Upload
others
View
1
Download
0
Embed Size (px)
Citation preview
i
2009 Asian Symposium on Organic Materials for Electronics and Photonics (ASOMEP 2009)
The 7th International OLED and PLED Materials Workshop in Taipei
December 14 (Monday) ndash December 15 (Tuesday) 2009
ASOMEP 2009 Final Program
Time Symposium
Session Dec 13th (Sun)
Symposium Session Dec 14th (Mon)
Symposium Session Dec 15th (Tue)
0800-0850 Registration and Check In
0850-0900 Opening Remarks (Prof Pi-Tai Chou NTU)
Chair Prof Pi-Tai Chou (NTU) Prof Hsiu-Fu Hsu (TKU)
0900-0925 Prof Kilwon Cho (Korea) Prof J A Gareth Williams (UK)
0925-0950 Prof Kung-Hwa Wei (NCTU) Prof Hwan Kyu Kim (Korea)
0950-1010 Coffee Break
Chair Prof Hsiu-Fu Hsu (TKU) Prof Yun Chi (NTHU)
1010-1035 Prof Dong Hoon Choi (Korea) Prof Chun-Guey Wu (NCU)
1035-1100 Prof Guillermo C Bazan (USA) Prof Jang-Joo Kim (Korea)
1100-1125 Deputy Director Jia-Ming Liu (ITRI) Prof Takashi Karatsu (Japan)
1125-1150 Prof Yun-Hee Kim (Korea) Prof Yong-Rok Kim(Korea)
1150-1320 Lunch and Poster Section
Chair Prof Chung-Chih Wu (NTU) Prof Man-Kit Leung (NTU)
1320-1345 Director Yusin Lin (AUO) Prof Wei-Fang Su (NTU)
1345-1410 Prof Osamu Ishitani (Japan) Prof Hironori Kaji (Japan)
1410-1435 Prof Eunkyoung Kim (Korea) Prof Hsiu-Fu Hsu (TKU)
1435-1500 Prof Ye Tao (Canada) Prof Wai-Yeung Wong (HK)
1500-1520 Coffee Break
Chair Prof Chien-Tien Chen (NTNU) Prof Yun Chi (NTHU)
1520-1545 Prof Nakjoong Kim (Korea) Prof MunPyo Hong (Korea)
1545-1610 Prof IDW Samuel (UK) Prof Changjin Lee (Korea)
1610-1635 Prof Wei Huang (China) Prof Eric Diau (NCTU)
1635-1700
Tour Section
Prof Cheolmin Park (Korea) Prof Tae-Dong Kim (Korea)
1700-1725
1725-1735 Prof Tetsuro Majima (Japan) Closing Remarks
(Prof Yun Chi)
1800-2030
Reception Hosts Prof Pi-Tai
Chou Yun Chi and Chien-Tien
Chen Dinner Closing Ceremony and Dinner
ii
ASOMEP 2009 Final Program
December 14 (Mon)
0800-0850 Registration and Check In
0850-0900 Opening Remarks Prof Pi-Tai Chou NTU Plenary Session I (Chair Prof Pi-Tai Chou)
0900-0925 Organic thin-film transistors based on organic semiconductor insulating polymer blends
Prof Kilwon Cho Korea 1
0925-0950 Main-chain and side-chain donor-acceptor conjugated polymers for bulk heterojunction
solar cell applications
Prof Kung-Hwa Wei NCTU 2
0950-1010 Coffee Break
Plenary Session II (Chair Prof Hsiu-Fu Hsu)
1010-1035 Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Prof Dong Hoon Choi Korea 3
1035-1100 Insight into the synthesis design and processing of narrow band gap organic
semiconducting polymers for solar cell fabrication Prof Guillermo C Bazan USA 4
1100-1125 Recent progress of OLED lighting at ITRI
Deputy Director Jia-Ming Liu ITRI 5
1125-1150 To Be Announced
Prof Yun-Hee Kim Korea 6 1150-1320 Lunch and Poster Section
Plenary Session III (Chair Chung-Chih Wu)
1320-1345 AMOLED as a green solution for display
Director Yusin Lin AUO 7
1345-1410 Control of photochemical and photophysical properties of rhenium(I) complexes using
intrerligand weak interaction between ligands
Prof Osamu Ishitani Japan 8
1410-1435 Patternable conductive polymers for organic device application
Prof Eunkyoung Kim Korea 9
1435-1500 Development of low-cost high efficiency organic solar cells
iii
Prof Ye Tao Canada 10
1500-1520 Coffee Break
Plenary Session IV (Chair Chien-Tien Chen)
1520-1545 To Be Announced
Prof Nakjoong Kim Korea 11
1545-1610 Organic semiconductors from solar cells to skin cancer treatment
Prof IDW Samuel UK 13
1610-1635 Pyrene-based organic semiconductors for high-performance optoelectronic devices
Prof Wei Huang China 14
1635-1700 Thin hybrid block copolymer micelle films with tunable electro-optic properties
Prof Cheolmin Park Korea 15
1700-1725 DNA electronics
Prof Tetsuro Majima Japan 16
1800-2030 Dinner
December 15 (Tue) Plenary Session I (Chair Hsiu-Fu Hsu)
0900-0925 Optimizing the efficiency of luminescent platinum complexes for colour NIR and white-light
OLEDs
Prof J A Gareth Williams UK 17
0925-0950 The unusual key issues on energy transfer pathway of lanthanide(III)-cored complexes for
highly efficient Ln3+ emission
Prof Hwan Kyu Kim Korea 18
0950-1010 Coffee Break
Plenary Session II (Chair Yun Chi)
1010-1035 Ruthenium sensitizers for all-purpose dye-sensitized solar cells
Prof Chun-Guey Wu NCU 19
1035-1100 Electrical doping in organic semiconductors display and other applications
Prof Jang-Joo Kim Korea 20
1100-1125 Photophysics and photochemistry of blue green and red phosphorescent
triscyclometalated Ir(III) complexes
Prof Takashi Karatsu Japan 21
1125-1150 Random lasing films with organic-inorganic-composites
Prof Yong Rok Kim Korea 22
iv
1150-1320 Lunch and Poster Section Plenary Session III (Chair Man-Kit Leung)
1320-1345 Toward high efficiency polymer-nanoparticle hybrid solar cell
Prof Wei-Fang Su NTU 23
1345-1410 Solid-state NMR analysis of materials for organic light-emitting diodes
Prof Hironori Kaji Japan 24
1410-1435 Gearing of molecules for highly correlated molecular packing
Prof Hsiu-Fu Hsu TKU 25
1435-1500 Functional metallophosphors as robust OLED materials for effective charge carrier
injectiontransport
Prof Wai-Yeung Wong HK 26
1500-1520 Coffee Break
Plenary Session IV (Chair Yun Chi)
1520-1545 Study of top ITO electrode formation for inverted top emission OLED
Prof MunPyo Hong Korea 27
1545-1610 Novel fullerene derivatives and printed organic solar cells
Prof Changjin Lee Korea 28
1610-1635 Highly efficient dye-sensitized solar cells based on porphyrin sensitizers and
one-dimensional TiO2 nanostructures
Prof Eric Diau NCTU 29 1635-1700 Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Prof Tae-Dong Kim Korea 30
1725-1735 Closing Remarks Prof Yun Chi NTHU
1800-2030 Closing Ceremony and Dinner
v
Poster Presentation
1 Synthesis and optical Properties of perylene bisimide and anthracene derivatives for optoelectronic
materials
Po-Jen Ku Institute of Chemistry Academia Sinica 31
2 Dibenzo[fh]thieno[34-b]quinoxaline-based small molecules for efficient bulk-heterojunction solar cells
Ying-Chan Hsu Institute of Chemistry Academia Sinica 32
3 Structurally simple dipolar organic dyes featuring 13-cyclohexadiene conjugated unit for dye-sensitized
solar cells
Kuan-Fu Chen Institute of Chemistry Academia Sinica 33
4 Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Ting National Taiwan University 34
5 Phenylbenzimidazolecarbazole-based bipolar materials for highly efficient deep-blue fluorescence
green-yellow phosphorescence host and white OLEDs
Liang-Chen Chi National Taiwan University 35
6 A spiro-configured ambiploar host material for impressively efficient signal-layer green
electrophosphorescent devices
Hsiao-Fan Chen National Taiwan University 36
7 Highly efficient carbazoleoxadiazole-based bipolar host materials for green phosphorescent OLEDs
Shuo-Hsien Cheng National Taiwan University 37
8 Polymer light emitting-diodes material containing unsymmetrical substituted group synthesis and their
optical electrochemical and electrochromic properties
Der-Jang Liaw National Taiwan University of Science and Technology 38
9 Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang National Taiwan Normal University 39
10 Highly stereoselectivity of photoisomerization by Increasing steric hindrance of inherent MOM-based
helicene structure
Chien-Hsing Chen National Taiwan Normal University 40
11 Doubly ortho-linked cis-stillbenefluorene hybrids as bipolar organic sensitizers materials for solar cell
applications
Wei-Shan Chao National Taiwan Normal University 41
12 Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent
Materials for Optoelectronic Applications
Yi Wei National Taiwan Normal University 42
vi
13 High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu National Taiwan Ocean University 43
14 Highly Efficient Green PhOLEDs with ET-type Host Material
Wen-Yi Hung National Taiwan Ocean University 44
15 White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin National Cheng Kung University 45
16 Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan Tamkang University 47
Oral Presentation
December 14 Monday
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
ii
ASOMEP 2009 Final Program
December 14 (Mon)
0800-0850 Registration and Check In
0850-0900 Opening Remarks Prof Pi-Tai Chou NTU Plenary Session I (Chair Prof Pi-Tai Chou)
0900-0925 Organic thin-film transistors based on organic semiconductor insulating polymer blends
Prof Kilwon Cho Korea 1
0925-0950 Main-chain and side-chain donor-acceptor conjugated polymers for bulk heterojunction
solar cell applications
Prof Kung-Hwa Wei NCTU 2
0950-1010 Coffee Break
Plenary Session II (Chair Prof Hsiu-Fu Hsu)
1010-1035 Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Prof Dong Hoon Choi Korea 3
1035-1100 Insight into the synthesis design and processing of narrow band gap organic
semiconducting polymers for solar cell fabrication Prof Guillermo C Bazan USA 4
1100-1125 Recent progress of OLED lighting at ITRI
Deputy Director Jia-Ming Liu ITRI 5
1125-1150 To Be Announced
Prof Yun-Hee Kim Korea 6 1150-1320 Lunch and Poster Section
Plenary Session III (Chair Chung-Chih Wu)
1320-1345 AMOLED as a green solution for display
Director Yusin Lin AUO 7
1345-1410 Control of photochemical and photophysical properties of rhenium(I) complexes using
intrerligand weak interaction between ligands
Prof Osamu Ishitani Japan 8
1410-1435 Patternable conductive polymers for organic device application
Prof Eunkyoung Kim Korea 9
1435-1500 Development of low-cost high efficiency organic solar cells
iii
Prof Ye Tao Canada 10
1500-1520 Coffee Break
Plenary Session IV (Chair Chien-Tien Chen)
1520-1545 To Be Announced
Prof Nakjoong Kim Korea 11
1545-1610 Organic semiconductors from solar cells to skin cancer treatment
Prof IDW Samuel UK 13
1610-1635 Pyrene-based organic semiconductors for high-performance optoelectronic devices
Prof Wei Huang China 14
1635-1700 Thin hybrid block copolymer micelle films with tunable electro-optic properties
Prof Cheolmin Park Korea 15
1700-1725 DNA electronics
Prof Tetsuro Majima Japan 16
1800-2030 Dinner
December 15 (Tue) Plenary Session I (Chair Hsiu-Fu Hsu)
0900-0925 Optimizing the efficiency of luminescent platinum complexes for colour NIR and white-light
OLEDs
Prof J A Gareth Williams UK 17
0925-0950 The unusual key issues on energy transfer pathway of lanthanide(III)-cored complexes for
highly efficient Ln3+ emission
Prof Hwan Kyu Kim Korea 18
0950-1010 Coffee Break
Plenary Session II (Chair Yun Chi)
1010-1035 Ruthenium sensitizers for all-purpose dye-sensitized solar cells
Prof Chun-Guey Wu NCU 19
1035-1100 Electrical doping in organic semiconductors display and other applications
Prof Jang-Joo Kim Korea 20
1100-1125 Photophysics and photochemistry of blue green and red phosphorescent
triscyclometalated Ir(III) complexes
Prof Takashi Karatsu Japan 21
1125-1150 Random lasing films with organic-inorganic-composites
Prof Yong Rok Kim Korea 22
iv
1150-1320 Lunch and Poster Section Plenary Session III (Chair Man-Kit Leung)
1320-1345 Toward high efficiency polymer-nanoparticle hybrid solar cell
Prof Wei-Fang Su NTU 23
1345-1410 Solid-state NMR analysis of materials for organic light-emitting diodes
Prof Hironori Kaji Japan 24
1410-1435 Gearing of molecules for highly correlated molecular packing
Prof Hsiu-Fu Hsu TKU 25
1435-1500 Functional metallophosphors as robust OLED materials for effective charge carrier
injectiontransport
Prof Wai-Yeung Wong HK 26
1500-1520 Coffee Break
Plenary Session IV (Chair Yun Chi)
1520-1545 Study of top ITO electrode formation for inverted top emission OLED
Prof MunPyo Hong Korea 27
1545-1610 Novel fullerene derivatives and printed organic solar cells
Prof Changjin Lee Korea 28
1610-1635 Highly efficient dye-sensitized solar cells based on porphyrin sensitizers and
one-dimensional TiO2 nanostructures
Prof Eric Diau NCTU 29 1635-1700 Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Prof Tae-Dong Kim Korea 30
1725-1735 Closing Remarks Prof Yun Chi NTHU
1800-2030 Closing Ceremony and Dinner
v
Poster Presentation
1 Synthesis and optical Properties of perylene bisimide and anthracene derivatives for optoelectronic
materials
Po-Jen Ku Institute of Chemistry Academia Sinica 31
2 Dibenzo[fh]thieno[34-b]quinoxaline-based small molecules for efficient bulk-heterojunction solar cells
Ying-Chan Hsu Institute of Chemistry Academia Sinica 32
3 Structurally simple dipolar organic dyes featuring 13-cyclohexadiene conjugated unit for dye-sensitized
solar cells
Kuan-Fu Chen Institute of Chemistry Academia Sinica 33
4 Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Ting National Taiwan University 34
5 Phenylbenzimidazolecarbazole-based bipolar materials for highly efficient deep-blue fluorescence
green-yellow phosphorescence host and white OLEDs
Liang-Chen Chi National Taiwan University 35
6 A spiro-configured ambiploar host material for impressively efficient signal-layer green
electrophosphorescent devices
Hsiao-Fan Chen National Taiwan University 36
7 Highly efficient carbazoleoxadiazole-based bipolar host materials for green phosphorescent OLEDs
Shuo-Hsien Cheng National Taiwan University 37
8 Polymer light emitting-diodes material containing unsymmetrical substituted group synthesis and their
optical electrochemical and electrochromic properties
Der-Jang Liaw National Taiwan University of Science and Technology 38
9 Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang National Taiwan Normal University 39
10 Highly stereoselectivity of photoisomerization by Increasing steric hindrance of inherent MOM-based
helicene structure
Chien-Hsing Chen National Taiwan Normal University 40
11 Doubly ortho-linked cis-stillbenefluorene hybrids as bipolar organic sensitizers materials for solar cell
applications
Wei-Shan Chao National Taiwan Normal University 41
12 Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent
Materials for Optoelectronic Applications
Yi Wei National Taiwan Normal University 42
vi
13 High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu National Taiwan Ocean University 43
14 Highly Efficient Green PhOLEDs with ET-type Host Material
Wen-Yi Hung National Taiwan Ocean University 44
15 White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin National Cheng Kung University 45
16 Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan Tamkang University 47
Oral Presentation
December 14 Monday
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
iii
Prof Ye Tao Canada 10
1500-1520 Coffee Break
Plenary Session IV (Chair Chien-Tien Chen)
1520-1545 To Be Announced
Prof Nakjoong Kim Korea 11
1545-1610 Organic semiconductors from solar cells to skin cancer treatment
Prof IDW Samuel UK 13
1610-1635 Pyrene-based organic semiconductors for high-performance optoelectronic devices
Prof Wei Huang China 14
1635-1700 Thin hybrid block copolymer micelle films with tunable electro-optic properties
Prof Cheolmin Park Korea 15
1700-1725 DNA electronics
Prof Tetsuro Majima Japan 16
1800-2030 Dinner
December 15 (Tue) Plenary Session I (Chair Hsiu-Fu Hsu)
0900-0925 Optimizing the efficiency of luminescent platinum complexes for colour NIR and white-light
OLEDs
Prof J A Gareth Williams UK 17
0925-0950 The unusual key issues on energy transfer pathway of lanthanide(III)-cored complexes for
highly efficient Ln3+ emission
Prof Hwan Kyu Kim Korea 18
0950-1010 Coffee Break
Plenary Session II (Chair Yun Chi)
1010-1035 Ruthenium sensitizers for all-purpose dye-sensitized solar cells
Prof Chun-Guey Wu NCU 19
1035-1100 Electrical doping in organic semiconductors display and other applications
Prof Jang-Joo Kim Korea 20
1100-1125 Photophysics and photochemistry of blue green and red phosphorescent
triscyclometalated Ir(III) complexes
Prof Takashi Karatsu Japan 21
1125-1150 Random lasing films with organic-inorganic-composites
Prof Yong Rok Kim Korea 22
iv
1150-1320 Lunch and Poster Section Plenary Session III (Chair Man-Kit Leung)
1320-1345 Toward high efficiency polymer-nanoparticle hybrid solar cell
Prof Wei-Fang Su NTU 23
1345-1410 Solid-state NMR analysis of materials for organic light-emitting diodes
Prof Hironori Kaji Japan 24
1410-1435 Gearing of molecules for highly correlated molecular packing
Prof Hsiu-Fu Hsu TKU 25
1435-1500 Functional metallophosphors as robust OLED materials for effective charge carrier
injectiontransport
Prof Wai-Yeung Wong HK 26
1500-1520 Coffee Break
Plenary Session IV (Chair Yun Chi)
1520-1545 Study of top ITO electrode formation for inverted top emission OLED
Prof MunPyo Hong Korea 27
1545-1610 Novel fullerene derivatives and printed organic solar cells
Prof Changjin Lee Korea 28
1610-1635 Highly efficient dye-sensitized solar cells based on porphyrin sensitizers and
one-dimensional TiO2 nanostructures
Prof Eric Diau NCTU 29 1635-1700 Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Prof Tae-Dong Kim Korea 30
1725-1735 Closing Remarks Prof Yun Chi NTHU
1800-2030 Closing Ceremony and Dinner
v
Poster Presentation
1 Synthesis and optical Properties of perylene bisimide and anthracene derivatives for optoelectronic
materials
Po-Jen Ku Institute of Chemistry Academia Sinica 31
2 Dibenzo[fh]thieno[34-b]quinoxaline-based small molecules for efficient bulk-heterojunction solar cells
Ying-Chan Hsu Institute of Chemistry Academia Sinica 32
3 Structurally simple dipolar organic dyes featuring 13-cyclohexadiene conjugated unit for dye-sensitized
solar cells
Kuan-Fu Chen Institute of Chemistry Academia Sinica 33
4 Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Ting National Taiwan University 34
5 Phenylbenzimidazolecarbazole-based bipolar materials for highly efficient deep-blue fluorescence
green-yellow phosphorescence host and white OLEDs
Liang-Chen Chi National Taiwan University 35
6 A spiro-configured ambiploar host material for impressively efficient signal-layer green
electrophosphorescent devices
Hsiao-Fan Chen National Taiwan University 36
7 Highly efficient carbazoleoxadiazole-based bipolar host materials for green phosphorescent OLEDs
Shuo-Hsien Cheng National Taiwan University 37
8 Polymer light emitting-diodes material containing unsymmetrical substituted group synthesis and their
optical electrochemical and electrochromic properties
Der-Jang Liaw National Taiwan University of Science and Technology 38
9 Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang National Taiwan Normal University 39
10 Highly stereoselectivity of photoisomerization by Increasing steric hindrance of inherent MOM-based
helicene structure
Chien-Hsing Chen National Taiwan Normal University 40
11 Doubly ortho-linked cis-stillbenefluorene hybrids as bipolar organic sensitizers materials for solar cell
applications
Wei-Shan Chao National Taiwan Normal University 41
12 Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent
Materials for Optoelectronic Applications
Yi Wei National Taiwan Normal University 42
vi
13 High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu National Taiwan Ocean University 43
14 Highly Efficient Green PhOLEDs with ET-type Host Material
Wen-Yi Hung National Taiwan Ocean University 44
15 White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin National Cheng Kung University 45
16 Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan Tamkang University 47
Oral Presentation
December 14 Monday
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
iv
1150-1320 Lunch and Poster Section Plenary Session III (Chair Man-Kit Leung)
1320-1345 Toward high efficiency polymer-nanoparticle hybrid solar cell
Prof Wei-Fang Su NTU 23
1345-1410 Solid-state NMR analysis of materials for organic light-emitting diodes
Prof Hironori Kaji Japan 24
1410-1435 Gearing of molecules for highly correlated molecular packing
Prof Hsiu-Fu Hsu TKU 25
1435-1500 Functional metallophosphors as robust OLED materials for effective charge carrier
injectiontransport
Prof Wai-Yeung Wong HK 26
1500-1520 Coffee Break
Plenary Session IV (Chair Yun Chi)
1520-1545 Study of top ITO electrode formation for inverted top emission OLED
Prof MunPyo Hong Korea 27
1545-1610 Novel fullerene derivatives and printed organic solar cells
Prof Changjin Lee Korea 28
1610-1635 Highly efficient dye-sensitized solar cells based on porphyrin sensitizers and
one-dimensional TiO2 nanostructures
Prof Eric Diau NCTU 29 1635-1700 Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Prof Tae-Dong Kim Korea 30
1725-1735 Closing Remarks Prof Yun Chi NTHU
1800-2030 Closing Ceremony and Dinner
v
Poster Presentation
1 Synthesis and optical Properties of perylene bisimide and anthracene derivatives for optoelectronic
materials
Po-Jen Ku Institute of Chemistry Academia Sinica 31
2 Dibenzo[fh]thieno[34-b]quinoxaline-based small molecules for efficient bulk-heterojunction solar cells
Ying-Chan Hsu Institute of Chemistry Academia Sinica 32
3 Structurally simple dipolar organic dyes featuring 13-cyclohexadiene conjugated unit for dye-sensitized
solar cells
Kuan-Fu Chen Institute of Chemistry Academia Sinica 33
4 Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Ting National Taiwan University 34
5 Phenylbenzimidazolecarbazole-based bipolar materials for highly efficient deep-blue fluorescence
green-yellow phosphorescence host and white OLEDs
Liang-Chen Chi National Taiwan University 35
6 A spiro-configured ambiploar host material for impressively efficient signal-layer green
electrophosphorescent devices
Hsiao-Fan Chen National Taiwan University 36
7 Highly efficient carbazoleoxadiazole-based bipolar host materials for green phosphorescent OLEDs
Shuo-Hsien Cheng National Taiwan University 37
8 Polymer light emitting-diodes material containing unsymmetrical substituted group synthesis and their
optical electrochemical and electrochromic properties
Der-Jang Liaw National Taiwan University of Science and Technology 38
9 Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang National Taiwan Normal University 39
10 Highly stereoselectivity of photoisomerization by Increasing steric hindrance of inherent MOM-based
helicene structure
Chien-Hsing Chen National Taiwan Normal University 40
11 Doubly ortho-linked cis-stillbenefluorene hybrids as bipolar organic sensitizers materials for solar cell
applications
Wei-Shan Chao National Taiwan Normal University 41
12 Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent
Materials for Optoelectronic Applications
Yi Wei National Taiwan Normal University 42
vi
13 High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu National Taiwan Ocean University 43
14 Highly Efficient Green PhOLEDs with ET-type Host Material
Wen-Yi Hung National Taiwan Ocean University 44
15 White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin National Cheng Kung University 45
16 Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan Tamkang University 47
Oral Presentation
December 14 Monday
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
v
Poster Presentation
1 Synthesis and optical Properties of perylene bisimide and anthracene derivatives for optoelectronic
materials
Po-Jen Ku Institute of Chemistry Academia Sinica 31
2 Dibenzo[fh]thieno[34-b]quinoxaline-based small molecules for efficient bulk-heterojunction solar cells
Ying-Chan Hsu Institute of Chemistry Academia Sinica 32
3 Structurally simple dipolar organic dyes featuring 13-cyclohexadiene conjugated unit for dye-sensitized
solar cells
Kuan-Fu Chen Institute of Chemistry Academia Sinica 33
4 Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Ting National Taiwan University 34
5 Phenylbenzimidazolecarbazole-based bipolar materials for highly efficient deep-blue fluorescence
green-yellow phosphorescence host and white OLEDs
Liang-Chen Chi National Taiwan University 35
6 A spiro-configured ambiploar host material for impressively efficient signal-layer green
electrophosphorescent devices
Hsiao-Fan Chen National Taiwan University 36
7 Highly efficient carbazoleoxadiazole-based bipolar host materials for green phosphorescent OLEDs
Shuo-Hsien Cheng National Taiwan University 37
8 Polymer light emitting-diodes material containing unsymmetrical substituted group synthesis and their
optical electrochemical and electrochromic properties
Der-Jang Liaw National Taiwan University of Science and Technology 38
9 Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang National Taiwan Normal University 39
10 Highly stereoselectivity of photoisomerization by Increasing steric hindrance of inherent MOM-based
helicene structure
Chien-Hsing Chen National Taiwan Normal University 40
11 Doubly ortho-linked cis-stillbenefluorene hybrids as bipolar organic sensitizers materials for solar cell
applications
Wei-Shan Chao National Taiwan Normal University 41
12 Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent
Materials for Optoelectronic Applications
Yi Wei National Taiwan Normal University 42
vi
13 High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu National Taiwan Ocean University 43
14 Highly Efficient Green PhOLEDs with ET-type Host Material
Wen-Yi Hung National Taiwan Ocean University 44
15 White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin National Cheng Kung University 45
16 Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan Tamkang University 47
Oral Presentation
December 14 Monday
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
vi
13 High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu National Taiwan Ocean University 43
14 Highly Efficient Green PhOLEDs with ET-type Host Material
Wen-Yi Hung National Taiwan Ocean University 44
15 White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin National Cheng Kung University 45
16 Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan Tamkang University 47
Oral Presentation
December 14 Monday
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Oral Presentation
December 14 Monday
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Organic Thin-Film Transistors Based on Organic Semiconductor Insulating Polymer Blends
Kilwon Cho
Department of Chemical Engineering Pohang University of Science and Technology Pohang 790-784 Korea (kwchopostechackr)
Organic semiconductor and insulating polymer
blends have been attracting considerable attention for organic electronic devices because the electronic properties of organic semiconductors can be combined with the low-cost environmentally stable and excellent mechanical characteristics of insulating polymers However degradation of the electrical performance in organic electronic devices based on the organic semiconductorinsulating polymer blends have been reported because of the decrease of interconnectivity in semiconducting component Therefore the development of a facile method for realizing high-performance low-semiconductor-cost device based on semiconductinginsulating polymer blend is of highly technological and academic significance
Here we demonstrate the versatile uses of organic semiconductorinsulating polymer blend for organic field-effect transistor (OFET) applications Firstly we report the semiconductor-top and dielectric-bottom bilayer structure by means of surface-induced vertical phase separation of poly(3-hexylthiohene) (P3HT) and poly(methyl methacrylate) (PMMA) blends [1] This bilayer structure exhibits the improved FET characteristics even at content of P3HT as low as 5 as well as one-step fabrication of low-voltage-driven device In the case of PMMA blends with small molecular organic semiconductor triethylsilylethynyl anthradithiophene (TES-ADT) vertically separated bilayer structure with TES-ADT crystals at the top and PMMA at the bottom are formed These phase-separated blend films serve as semiconducting (TES-
ADT) and dielectric (PMMA) layers in high performance FETs (ie with field-effect mobilities as high as 06 cm2V-1s-1 and nearly zero hysteresis) [2] Further we demonstrate that P3HT blends with
amorphous polystyrene (a-PS) using a marginal solvent (ie CH2Cl2) or solvent mixture with controlled solubility allows blend film to have the unique structure with P3HT nanowires embedded in PS matrix The P3HT molecules in these blends form highly crystalline interconnected nanowire networks dispersed in PS matrix which is extremely beneficial for keeping connectivity at content of P3HT as low as 3 wt and improving environmental stability [3 4] In addition these blend structure can be successfully produced by using inkjet printing technique [5] and organic semiconductorinsulating polymer blend may offer an excellent way to the direct-write fabrication of OFETs with low semiconductor cost high environmental stability References [1] L Qiu J A Lim X Wang W H Lee M Hwang KCho Adv Mater 2008 20 1141 [2] W H Lee J A Lim D Kwak J H Cho H S Lee H H Choi K Cho Adv Mater 2009 published-on line [3] L Qiu W H Lee X Wang J S Kim J A Lim D Kwak S Lee KCho Adv Mater 2009 21 1349 [4] L Qiu X Wang W H Lee J A Lim J S Kim D Kwak K Cho Chem Mater 2009 21 4380 [5] J A Lim W H Lee H S Lee J H Lee Y D Park K Cho Adv Funct Mater 2008 18 229
Kilwon Cho Seoul National University (BS 1980 MS 1982 in Applied Chemistry) The University of Akron (PhD 1986 in Polymer Science) IBM Research Center (Visiting Scientist 1987) Professor at POSTECH (1988 in Chemical Engineering) Research field polymer surface interface and thin film organic electronics (organic transistors organic photovoltaic solar cells) Current research interests development of printing-based organic field-effect transistors and organic photovoltaics
1
O-1
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Main-chain and Side-Chain Donor-Acceptor Conjugated Polymers for Bulk Heterojunction Solar Cell Applications
By Kung-Hwa Wei Department of Materials science and Engineering National Chiao Tung University Hsinchu Taiwan
e-mail khweimailnctuedutw
In this talk I will discuss the various prospects of some synthesized main-chain donor-acceptor and side-chain donor-acceptor conjugated polymers for blending with fullerenes to form bulk heterojunction solar cells This discussion involves both the materials and devices issues In particular I will present the results of a new kind of intramolecular donorndashacceptor side-chain-tethered phenanthrenyl-imidazole polythiophene (PHPIT) such a molecular architecture not only can increase the breadth of the wavelength of the light absorbed but also has the advantage of allowing charge separation through sequential transfer of electrons The device physics of PHPITfullerene nanocomposite will be covered Moreover the results of a new main-chain conjugated copolymer consisting of cyclopentadithiophene and benzopyridine units with full visible light absorption will be also discussed The last part of my talk is concerned with the nano-phase separation of polythiophene and fullerene in the active layer that involves holes and electrons transport to their respective electrodes
2
O-2
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Organic Soluble Deoxyribonucleic Acid (DNA) for Electronics and Optoelectronics
Dong Hoon Choi
Department of Chemistry Korea University Seoul Korea dhchoi8803koreaackr
Double-stranded (ds) DNA obtained from salmon
sperm are interesting biodegradable and environmentally
friendly biomacromolecules Because of the regular
sequence of the four base pairs in ds-DNA and the
abundance of π electrons ds-DNA can be used in novel
electronic devices as an electroactive material However
the hydrophilichygroscopic nature of natural ds-DNA
interferes with the study of electronic properties under
ambient conditions even in an inert atmosphere
Therefore we modified the structure of natural DNA into
organic soluble functional DNA
One example is described as follows The organically
functionalized DNA as an emitting host material was
employed for electrophosphorescent devices We
synthesized organically soluble DNA containing
dodecylcarbazolyl side-chain moieties (Cz-DNA) that
make the DNA less hydrophilic and improve the host
properties such as carrier mobility miscibility and the
effect of energy transfer on the guest Ir(III) complex
Cz-DNA showed good film-forming properties under
ambient conditions
We used a double layer of poly(34-
ethylenedioxythiophene) poly(styrenesulfonate)
(PEDOTPSS) and POx-TPACz in multilayer
electrophosphorescence PLEDs and fac-tris(3-((9H-
carbazol-9-yl)methyl)-2-phenylpyridinato-C2N)iridium
(III) (Ir(Cz-ppy)3) as an emissive carrier recombination
center to determine the electrical conductivity of the Cz-
DNA host in a device Significant improvement in
luminous efficiency and brightness was achieved by
doping Ir(Cz-ppy)3 into Cz-DNA which was blended
with an electron-transport molecule 5-4-tert-
butylphenyl-134-oxadiazole (PBD)
Dong Hoon Choi b 1960 in Seoul Korea Seoul National University (BS 1984 MS 1986)
University of Michigan (PhD 1991 Prof R Zand) The State Univ of New York at Buffalo
(Postdoc 1992 Prof P N Prasad) Assistant Associate Full Professor Kyung Hee University
(1995-2005) Associate Full Professor Korea University (2005-present) Research fields
Semiconducting Materials for TFT and OPV OLED Functional Nanofibers Nonlinear optical
Materials Bio-related Materials Functional DNA
Cz-DNA
Ir(Cz-ppy)3
Voltage (V)-2 0 2 4 6 8 10 12 14
Cur
rent
den
sity
(mA
cm
2 )
0
40
80
120
160L
umin
ance
(cd
m2 )
100
101
102
103
GlassITO
PEDOTPSS (30 nm)
Cz-DNA PBD Ir(Cz-ppy)3(20~40 nm)
TAZ (15 nm)Bphen (25 nm)LiF (08 nm)
Al (500nm)
POx-TPACz (10 nm)
3
O-3
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Insight into the synthesis design and processing of narrow band gap organic semiconducting polymers for solar cell fabrication
Guillermo C Bazan
Department of Materials University of California Santa Barbara CA 93106 USA bazanchemucsbedu
High charge separation efficiency combined with the
reduced fabrication costs associated with solution
processing (printing and coating) and the potential for
implementation on flexible substrates make ldquoplasticrdquo
solar cells a compelling option for tomorrowrsquos
photovoltaics The control the donoracceptor
morphology in bulk heterojunction materials as required
for achieving high power conversion efficiency have is
therefore of primary concern We showed that by
incorporating a few volume percent of high boiling point
additive the power conversion efficiency of photovoltaic
cells (AM 15 conditions) is increased from 28 to 55
[1] Subsequent efforts centered on understanding the
mechanism of action of the additives and this will be
discussed in some detail [234] More recently the
improved synthesis of polymers has been studied in
particular those backbone systems that lead to
aggregation in solution and high performance devices
We will present polymerization procedures that lead to
high molecular weight product in short reaction times
and involve simple purification protocols Emerging
structurefunction relationships will be examined as
well as those polymer systems that allow fabrication of
devices that have power conversion efficiencies
approaching 6
QuickTimeand a decompressor
are needed to see this picture
References (a) Controlled Beta-Phase Formation in Poly(99-di-n-Octylfluorene) by Processing with Alkyl Additives
Peet J Bracker E Xu YH Bazan GC Adv Mat 2008 20 1882-1892 (b) The Role of Processing in the
Fabrication and Optimization of Plastic Solar Cells Peet J Senatore ML Heeger AJ Bazan GC Adv Mat 2009
21 1521-1527 (c) Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-
Performance Bulk Heterojunction Solar Cells Coffin RC Peet J Rogers J Bazan GC Nat Chem 2009 1 657-
661
Guillermo C Bazan b 1963 in Mendoza Argentina B Sc University of Ottawa Canada
PhD MIT (Richard R Schrock supervisor) Current position Professor of Materials and
Chemistry amp Biochemistry UCSB Research fields organic semiconducting materials with
special emphasis on polymerization reactions and processing methods that yield improved
optoelectronic devices
4
O-4
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Recent Progress of OLED Lighting at ITRI
Jia-Ming Liu Meng-Ting Lee Heh-Lung Huang Jin-Sheng Lin Miao-Tsai Chu Mei-Rurng Tseng
Material and Chemical Research Laboratories Industrial Technology Research Institute (ITRI) Chutung 310
Hsinchu Taiwan
Organic light-emitting devices are expected to have some unique features that are not available from
traditional lighting sources for instance large-sized flat shape and mercury-free In this article we
introduce our new approaches-composite emitters and double emitting layer for achieving high power
efficiency of blue phosphorescent OLED (Fig 1) As compared to that of conventional devices the efficiency
of composite emitters and double emitting layer approaches for blue PHOLEDs was significantly improved
by a factor more than 2 and 18 respectively Moreover we also introduce our own highly efficient yellow
thiopyridinyl-based iridium complex with the efficiency of 403 cdA for white OLED Besides the efficiency of
new-developing yellow thiopyridinyl-based iridium complex is 628 cdA With these new approaches and
material the white OLED with a power efficiency of 55lmW can be achieved
(a) (b) (c)
FIG 1 (a) Composite emitter concept for blue PHOLEDs (b) double emission layers device architecture for
blue PHOLEDs (c)white OLED device performance based on double emission layers concept (inset EL
spectra with different brightness)
References
[1] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 92 pp 173305 (2008)
[2] M T Lee J S Lin M T Chu and M R Tseng Appl Phys Lett 94 pp 083506 (2009)
[3] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh Taiwan Patent I242999 2005
[4] K H Shen S T Yeh H L Huang I H Shen M T Chu and T S Hsieh US Patent 7445857 2008
5
O-5
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Prof Yun-Hee Kim
To Be Announced
6
O-6
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
AMOLED as a green solution for display
Director Yusin Lin Titles
bull AUO green solutions amp achievements
bull AMOLED as a green solution for display
bull Backplane technologies for AMOLED
bull Unique applications of AMOLED display
bull Future challenges of OLED TV
7
O-7
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Control of photochemical and photophysical properties of rhenium(I) complexes using intrerligand weak interaction
between ligands
Osamu Ishitani Tatsuki Morimoto Hideaki Tsubaki Megumi Ito Kazuhide Koike Department of Chemistry Tokyo Institute of Technology Tokyo Japan
e-mail ishitanichemtitechacjp
Control of photochemical photophysical and electrochemical properties of transition metal complexes is of great interest because of the advantages of these complexes in fields of chemistry as diverse as photo- and electro-catalysts photonic sensors photochemical energy and electron transfer chemi- and electro-luminescence molecular electronics and photonics Intramolecular interactions between ligands have been successfully applied as a novel tool for controlling various properties of a series of cistrans-[Re(dmb)(CO)2(PR3)(PR3)]+ type complexes (dmb = 44-dimethyl-22-bipyridine) in the ground state and in the excited state For the rhenium complexes with two triarylphosphine ligands P(p-XPh)3 the dmb ligand was sandwiched by four aryl rings having CH(aryl)-π(pyridine)-π(aryl) interactions12 Properties of the complexes associated mainly with the dmb ligand are strongly affected by the intramolecular interactions (1) UVvis absorptions to the πminusπ and 1MLCT excited states were both red-shifted but (2) emission from the 3MLCT excited state was blue-shifted (3) the lifetime of the 3MLCT excited state was prolonged up to threefold These effects of the interligand interaction should give advantageous properties to the Re(I) complexes as photocatalyst ie longer absorption wavelength long lifetime of the reactive excited state and stronger oxidation power in the excited state Actually cistrans-[Re(dmb)(CO)2P(p-XPh )32]+ works as a good photocatalyst for CO2 reduction (ΦCO = 02 TNCO = 17)23
References [1] H Tsubaki A Sekine Y Ohashi K Koike H Takeda and O Ishitani J Am Chem Soc 2005 127 15544 [2] H Tsubaki S Tohyama K Koike and O Ishitani Dalton Transactions 2005 385 [3] H Tsubaki A Sugawara H Takeda B Gholamkhass K Koike O Ishitani Res Chem Intermediat 2007 33 37-48
Osamu Ishitani 石谷 治 b 1959 in Hiroshima Japan Kobe Univ (BS 1982) Osaka Univ (PhD 1987) Hahn-Meitner Institute Visiting Researcher (1987) National Institute for Resources and Environment Researcher (1988) Senior Researcher (1991) Univ of North Carolina at Chapel Hill Visiting Researcher (1993) Saitama Univ Associate Professor (1995) Tokyo Institute of Technology Associate Professor (2002) Professor (2006-) Research filed Photochemistry of transition metal complexes Photocatalyst Solar energy conversion
Figure Interligand interaction in
[Re(dmb)(CO)2(PPh3)2]+
8
O-8
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Patternable conductive polymers for organic device application
Yuna Kim Sehwan Kim Jungmok You Jeonghun Kim Eunkyoung Kim
Department of Chemical and Biomolecular Engineering Yonsei University
262 Seongsanno Seodaemun-gu Seoul 120-749 Korea eunkimyonseikr
Patterning of active polymer films at micro or nano scales
has been an important issue for the organic devices The
formation of photoactive or conductive polymer patterns
by simple process is a key requirement for various
practical applications such as integrated circuits solar
cells electrochromic displays and bioengineering
Electronic control and cell engineering based on
patternable conducting polymers were examined using
photoactive polymers New photoactive polymers were
synthesized by attaching methacrylate or vinylene groups
to afford patternable conducting polymersa
Thus nanostructure of the polythiophenes was controlled
by the photoreaction of methacrylate pendant groups in
the polymer chain The synthesized photoreactive
conducting polymers or its precursor afforded thin films
of conducting polymers via spin coating or vapor phase
polymerization respecrively Photoreaction of the
conducting polymers led to patterns in different
dimension The surface morphology and charge
transport properties of the polymer films were affected
by the degree of the photo cross-linking reaction as well
as pattern dimension The application potential of the
patterned films was examined by characterizing the
properties of the conducting film as an active organic
photovoltaics electrochromic devices and cell culture
systemb
References (a) Jeonghun Kim Hyunjin Oh Eunkyoung Kim J Mater Chem 2008 18 4762-4768 (b) Jungmok
You June Seok Heo Jiyea Lee Han-Soo Kim Hyun Ok Kim and Eunkyoung Kim Macromolecules 2009
3326ndash3332
Eunkyoung Kim Born in 1959 in Seoul South Korea Yonsei University (BS 1982) Seoul
National Univ (MS 1984) University of Houston (PhD 1990 Prof J K Kochi)
University of Houston (Postdoc1990-92 Prof J K Kochi) Korea Research Institute of
Chemical Technology (KRICT research scientist 1992-2004 Division Chair 2002-2004)
Yonsei Univ (Professor 20049 ~ current) Research fields Chromogenic polymers
photopolymers and charge transport in polymeric media for organic circuitry 3D
information storage and patterning
9
O-9
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Development of Low-Cost High Efficiency Organic Solar Cells
Ye Tao
Institute for Microstructural Sciences National Research Council of Canada Ottawa Canada K1A 0R6
yetaonrc-cnrcgcca
Using photovoltaic (PV) effect to generate electricity
from solar energy represents a highly appealing solution
to our need for clean abundant and renewable energy
sources and to our desire for protecting the environment
Organic semiconductor based PV cells are viewed as one
of the most promising candidates for low cost solar cells
due to the low material cost and the possibility of using
wet processes such as spin-coating ink-jet and roll-to-
roll printing for fabrication on flexible plastic substrates
In this talk I will present our recent work on the
development of bulk heterojunction solar cells using
polycarbazole derivatives and discuss the effects of the
device architectures thin film processes on the light
absorption power conversion efficiency and current-
voltage characteristics of the solar cells Through device
structure optimization and process improvement we
have reached a power conversion efficiency of 60
with polycarbazole derivative based solar cells under
one sun of AM15G simulated illumination
References (a) N Blouin A Michaud D Gendron S Wakim M Belletecircte G Durocher Y Tao and M Leclerc J AM CHEM SOC 2008 130 732-742 (b) T-Y Chu S Alem P G Verly S Wakim J P Lu Y Tao S Beaupreacute M Leclerc F Beacutelanger D Deacutesilets S Rodman D Waller and R Gaudiana Appl Phys Lett 95 063304 (2009)
Ye Tao Nanjing Univeristy (BS 1982 M Sc 1986 Prof Feng Duan) Eacutecole Polytechnique
University of Montreal Canada (PhD 1993 Prof Author Yelon) Swiss Federal Institute of
Technology Zuumlrich (ETH-Zuumlrich) Switzerland (PDF 1995-98 Prof Peter Guumlnter) National
Research Council of Canada Inst for Microstructural Sci (1998-present) Senior Research
Officer group leader of the Organic Materials and Devices Group Research fields organic
semiconductor materials and devices surfaces and interfaces
-12 -08 -04 00 04 08 12
-10
0
10
20
30ITOPEDOT PCDTBT[70]PCBM LiFAl
JSC= -108 mAcm2
VOC= 088 VFF= 63η= 60
Cur
rent
den
sity
(mA
cm
2 )
Voltage (V)
dark 100 mWcm2
300 400 500 600 700 8000
10
20
30
40
50
60
70
80
Wavelength (nm)
Ext
erna
l Qua
ntum
Effi
cien
cy (
)
10
20
30
40
50
60
70ITOPEDOT PCDTBTPC70BM LiFAl
Reflectance (
)
10
O-10
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Nakjoong Kim Prof Dr
Organic Photonic and Electronic materials amp Department of Chemistry Hanyang University
Haengdang-Dong Seongdong-Gu Seoul 133-791 Korea Tel +82-2-2220-0935(O) Fax +82-2-2295-0572
Email kimnjhanyangackr amp Homepage httpopemhanyangackr
Educations 1973 2 Department of Chemical Seoul National University (BS) 1978 2 Department of Chemical Seoul National University (MS)
(Advisor Prof Seihun Chang) 1978 8 ndash 1983 8 Department of Chemical University of Texas at Austin (PhD) (Advisor Prof Stephen E Webber)
1983 8 ndash 20002 Functional Polymers Laboratory KIST (Senior Researcher) 1984 1 ndash 198412 Department of Chemical University of Texas at Austin (Visiting Researcher)
199810 - 2007 5 Director Creative Research Initiative Center for Organic Photorefractive Materials at Hanyang University 2000 3 - present Department of Chemistry Hanyang University (Professor)
2007 7 ndash present Director Center of IBENT Sciecnce Technology 2009 3 ndash present Director Research Institute for Natural Sciences at Hanyang University
Awards 1996 Testimonial from prime minister
Academic Related Careers
1987 - 1988 Secretary at the Polymer Society of Korea 1989 - 1990 Financial Secretary at the Polymer Society of Korea
11
O-11
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
1993 Financial Secretary at the Korean Chemical Society 1997 - 1999 Editorial Board in the Journal of Bulletin of Korean Chemical
Society at the Korean Chemical Society 1998 General Director at the Polymer Society of Korea 1998 ndash 2008 Chairman at Korea Japan Joint Forum
1999 Managing Director at the Polymer Society of Korea
2000 International Advisory Committee at International Conference on Organic Nonlinear Optics
2000 ndash 2001 Chairman in the Division of ldquoMolecular Electronics amp Devicesrdquo at the Polymer Society of Korea
2004 Chairman in the Division of ldquoPolymer Chemistryrdquo
at the Korean Chemical Society 2004 - 2005 Scientific Affairs Director at the Polymer Society of Korea
2004 - 2007 Vice-president at Korean Society for Imaging Science and Technology
2005 2007 Board of Trustees at the Korean Chemical Society 2006 Auditor at the Polymer Society of Korea 2006 Vice-president at the Korean Chemical Society 2006 ndash 2007 Conference Chairs amp Editorial Board in the Division of ldquoOrganic Photonic
Materials and Devicesrdquo at the SPIE photonic west 2007 Vice-president at the Polymer Society of Korea 2008 ndash 2009 President at Korean Society for Imaging Science and Technology 2009 - Honorary Chairman at Korea Japan Joint Forum
12
O-11
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
ORGANIC SEMICONDUCTORS FROM SOLAR CELLS TO SKIN CANCER TREATMENT
Prof IDW Samuel
Director of the Organic Semiconductor Centre
SUPA School of Physics and Astronomy University of St Andrews
St Andrews Organic semiconductors are very promising optoelectronic materials allowing simple fabrication of devices such as LEDs solar cells and lasers This talk will give an overview of work at the Organic Semiconductor Centre in St Andrews and then focus on two aspects of recent progress First it will explain the crucial role of exciton diffusion in (solid state) organic solar cells The development of methods using time-resolved fluorescence measurements to measure exciton diffusion will be described and the results reported Second it will show how skin cancer is a major and rapidly growing problem and that polymer LEDs provide a revolutionary new approach to the treatment of many skin cancers
13
O-12
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Pyrene-based Organic Semiconductors for High-performance Optoelectronic Devices Ling-hai Xie Chao Tang Wen-Yong Lai and Wei Huang
Jiangsu Key Laboratory for Organic Electronics amp Information Displays and Institute of Advanced Materials (IAM)
Nanjing University of Posts and Telecommunications (NUPT) 9 Wenyuan Road Nanjing 210046 China
Phone +86 25 8586 6008 Fax +86 25 8586 6999 Email iamwhuangnjupteducn
Polycyclic aromatic hydrocarbons (PAHs) become a
fascinating class of planar π-systems with unique optoelectronic properties and π-π supramolecular interaction Bulky group-functionalized carbon-rich planar polycyclic aromatic hydrocarbons could improve photoluminescence efficiency and hole-injection ability while keep high carrier mobility
Pyrene is one of well-known PAHs extensively applied in the field of bio-science and technology we combined pyrene into noncoplanar oligofluorenes or polyfluorenes and investigated their structure-property relationships and device performances The following are some recent results (1) the effect of phenylfluorenyl moieties (PFMs) as noncoplanar elements on the π-π stacking interaction was demonstrated by single-crystal X-ray and simulation (2) Various pyrene-based complex diarylfluorenes and spiro-functionalized pyrene was designed and synthesized to obtain the highly efficient blue OLED with 308
cdA12 (3) Multiarmed frameworks have been introduced to suppress dimmerization of pyrene structures for solution-processable light-emitting macromolecules3 Several attempts have also been made to develop the solution-processable small molecule blue and white organic light emitting diodes45 Pyrene-functionalized organic semiconductors were demonstrated to be efficient solution processable light emitting molecular glass (4) We designed hyperbranched interrupted π-conjugated polymers end-capped with high carrier-mobility moieties obtained stable light-emitting materials with low driving voltage6 (5) Pyrene-based electrolytes or surfactants have recently been designed for further improvement of OLED performance Polycyclic aromatic hydrocarbons modified with various functional groups will be promising candidates for high-performance optoelectronic devices
2PPF
O
2PPPF
O
2PE-PPF
C6H13C6H13
H
n
C6H13
C6H13
Hn
C6H13C6H13
Hn
C6H13
C6H13
H
n
n = 1 (T1)n = 2 (T2)n = 3 (T3)
References (1) Tang C Liu F Xia Y J Lin J Xie L H Zhong G Y Fan Q L Huang W Org Electron 2006
7 (3) 155-162 (2) Tang C Liu F Xia Y J Xie L H Wei A Li S B Fan Q L Huang W J Mater Chem
2006 16 (41) 4074-4080 (3) Liu F Lai W Y Tang C Wu H B Chen Q Q Peng B Wei W Huang W
Cao Y Macromol Rapid Commun 2008 29 (8) 659-664 (4) Liu F Tang C Chen Q Q Li S Z Wu H B Xie
L H Peng B Wei W Cao Y Huang W Org Electron 2009 10 (2) 256-265 (5) Liu F Tang C Chen Q Q
Shi F F Wu H B Xie L H Peng B Wei W Cao Y Huang W J Phys Chem C 2009 113 (11) 4641-
4647(6) Liu F Liu J-Q Liu R-R Hou X-Y Xie L H Wu H B Tang C Wei W Cao Y Huang W J
Polym Sci Part A Polym Chem 2009 47(23) 6451-6462
Wei HUANG b 1965 in Hebei Province China Peking University (BS 1983 Ph D 1992 Prof Y-
Q Tang) National University of Singapore (NUS) (Postdoc 1993) Senior Research Fellow by
IMRE (1998) Distinguished Professor Fudan University (2002) Initiated and established the
Institute of Advanced Materials (IAM) at Nanjing University of Posts and Telecommunications
(2007) Research fields Organic electronics Electroluminescent polymeric Materials Water-soluble
conjugated polymers for applications in biosensor Functional polymeric materials OLED-based
flat-panel displays Applications of photoelectron spectroscopy Molecular modeling
14
O-13
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Thin Hybrid Block Copolymer Micelle Films with Tunable Electro-optic Properties
Cheolmin Park Jinwoo Sung Himadri Acharya Department of Materials Science and Engineering Yonsei University Seoul Korea
cmparkyonseiackr
The nanostructures of block copolymers are of great
importance since they are useful for fabrication of
nanocomposites with the functional materials such as
metal nanoparticles quantum dots and single-wall carbon
nanotubes (SWNTs) We describes a novel method to
fabricate a thin composite film based on spin coating in
which surface plasmon bands of Au and Ag nanoparticles
are effectively coupled with each other due to position
selective deposition of both nanoparticles on a self
assembled block copolymer structure Simple solution
blending and subsequent spin coating of Au nanoparticles
(NPs) and a block copolymer micelles containing Ag NPs
in the core regions offers a facile route for controlling
coupled surface plasmon band (SPB) of the two NPs over
100 nm in wavelength in thin solid films (Figure b) The
self assembled composite structure where Ag and Au NPs
are preferentially located in the core and corona regions
of the micelles respectively allows not only a controlled
inter-particle distance but also homogeneous dispersion of
the NPs throughout film
In the second part we report a novel method to
disperse SWNTs in organic solvents The method is based
on treatment of SWNTs with block copolymer micelles
The micelles of a poly(styrene)-b-poly(4vinyl pyridine)
(PS-b-P4VP) copolymer physically absorbed on surface
of SWNTs provide good stability of the SWNT In order
to utilize the SWNTblock copolymer suspensions for
thin film applications we develop a new way for
fabricating a transparent thin film of block
copolymerSWNT composite based on spin coating with
low electric resistance The selective doping of
HAuCl43H2O metal salts in a self assembled block
copolymer nanostructure which provides a good
stability of SWNTs as a dispersant in the film allows us
to tune the conductance in the range of more than two
orders of magnitude with the transparency of the film
maintained
References (a) J Sung P S Jo H Shin J Huh B G Min D H Kim C Park Adv Mater 20 1505 2008 (b) H
Acharya J Sung K Tamada C Park Chemistry of Materials 21(18) 4248 2009
Cheolmin Park b 1970 in Pusan Korea Seoul National University (BS 1992) Seoul National University (MS 1995)
Massachussetts Institute of Technology (PhD 2001 Prof E L Thomas) Harvard University (Postdoc 2002 Prof G
Whitesides) Assistant Professor Yonsei University (2006) Associate Professor Yonsei University
Research fields Self assembled polymers such as block copolymers and semi-crystalline polymers
nanopatterning unconventional lithography nanocomposites organic electronic devices including
ferroelectric memory organic transistors
15
O-14
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
DNA Electronics
Tetsuro Majima
The Institute of Scientific and Industrial Research (SANKEN) Osaka University Osaka 567-0047 Japan
majimasankenosaka-uacjp
Charge transfer in DNA the base of DNA electronics
attracts wide attention because such charge transfer may
be a factor leading to DNA damage within a cell Thus
detailed studies on charge transfer in DNA are underway
even in very recent We have been working on charge
transfer in DNA mostly by means of the transient
absorption measurement(1)
The electric conduction is confirmed in DNA duplex as
expected for the stacked π-electron systems Relatively
high charge mobility long-range charge transport and
sequence dependence are important information obtained
by the preceding studies Still understanding on the
charge transfer seems to be limited As a wire for nano-
architecture characteristics of DNA as charge transport
media should be fully understood I would like to
introduce our recent work on charge transfer in DNA
and its application for single-base mismatch detection
and sequence independent charge transfer in DNA
together with rapid charge transfer which can be
attained by replacing adenine with deazaadenine
References (1) K Kawai et al Narture Chem 1(2) 156-159 (2009) J Am Chem Soc (Commun) 131(19) 6656-6657 (2009) ChemPhysChem on the web J Phys Chem B 112(7) 2144-2149 (2008) Chem Eur J 14(12) 3721-3726 (2008) Chem Commun 2656-2658 (2008) Nucl Acids Res 36(17) 5562ndash5570 (2008) Proc Nat Acad Sci USA 104(27) 11179-11183 (2007) Angew Chem Int Ed 46(35) 6681-6683 (2007) J Phys Chem B 111(9) 2322-2326 (2007) Chem Eur J 13(8) 2386-2391 (2007)
Tetsuro Majima b 1952 Osaka University (BS 1975 MS 1977 PhD 1980) Research Associate University of Texas at Dallas (1980-82) Guest Researcher The Institute of Physical and Chemical Research (RIKEN) (82-83) Researcher (83-92) Senior Researcher (92-94) Assoc Professor Osaka University (94-97) Professor (97-) Senior Editor of Langmuir American Chemical Society (07-) Professor of the WCU project in Korea University (09-) Research Field Photochemistry Radiation Chemistry Supramolecular chemistry Multi-laser chemistry Electron Transfer Chemistry Biomolecular Chemistry Single-molecular Chemistry
16
O-15
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Oral Presentation
December 15 Tuesday
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Optimizing the Efficiency of Luminescent Platinum Complexes for Colour NIR and White-Light OLEDs
J A Gareth Williams
Department of Chemistry University of Durham Durham DH1 3LE UK jagwilliamsdurhamacuk
Light-emitting complexes of 3rd row transition metal
ions are potential phosphors for OLEDs High spin-
orbit coupling constants facilitate emission from the
triplet states that are normally wasted in a purely organic
device The factors which must be taken into account in
the design of highly emissive Pt(II) complexes will be
revieweda before considering the properties of a class of
cyclometallated complexes under investigation in our
laboratory
These compounds are based on N^C^N-coordinating
ligands where C is a cyclometallating phenyl ring and N
represents a heterocyclic unit (eg 2-pyridyl 2-8-
quinolyl 1-isoquinolyl 1-pyrazolyl)b The simplest
such structure is shown below (R=R=H X=Cl) This
complex and many of its derivatives have exceptionally
high quantum yields (up to 085) which are rationalized
in terms of the rigidity imparted by the terdentate
structure and a short PtndashC bond which raises the energy
of potentially deactivating d-d states
Functionalisation of the N^C^N ligand or a judicious
choice of the ligand occupying the 4th coordination site
X (eg X = halides thiolates acetylides) allows excited
state energies to be tuned over almost the entire visible
range TD-DFT calculations assist in interpreting
substituent effects The complexes form excimers at
elevated concentrations ndash and sometimes in the solid
state according to packing ndash which emit efficiently in
the red region of the spectrum eg the figure shows the
spectra from crystals of two different polymorphs of one
complex By combining excimer emission with the
green-blue light of the isolated molecules high-
efficiency white-light-emitting devices are possible eg
external quantum efficiency up to 18 at 500 cd mndash2
CIE = (033 038)c Emerging strategies for
controlling the excimer energy to optimize the WOLED
characteristics will be discussed
N NPt
X
R
RR
References (a) Williams JAG Top Curr Chem 2007 281 205 (b) Williams JAG Chem Soc Rev 2009 38
1783 (c) Cocchi M Kalinowski J Fattori V Williams JAG Appl Phys Lett 2009 94 073309
J A Gareth Williams b 1970 in Manchester UK University of Oxford (BA 1992) University of
Durham (PhD 1995 Prof D Parker) Universiteacute Louis Pasteur (Postdoc 1996 Prof J-P Sauvage)
Lecturer (1998) then Senior Lecturer (2006) University of Durham Research fields synthesis amp
excited state properties of coordination compounds development of highly luminescent complexes for
light-emitting devices sensing and bioimaging investigation of synthetic strategies to polynuclear
complexes and energy transfer processes therein
0
20
40
60
80
100
400 500 600 700 800
emis
sion
inte
nsity
(au
)
wavelength nm
17
O-16
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
The Unusual Key Issues on Energy Transfer Pathway of Lanthanide(III)-cored Complexes for Highly Efficient Ln3+ Emission
Yu-Kyung Eom Jung Hwan Oh Bok Ju Song and Hwan Kyu Kim
Center for Advanced Photovoltaic Materials (ITRC) amp Department of Advanced Materials Chemistry
Korea University (Sejong) Korea Email hkk777koreaackr
The development of luminescent lanthanide
complexes has been attracted considerable attention
because of a wide variety of applications such as planar
waveguide amplifiers light-emitting diodes and MRI
contrast agent The complexation of luminescent Ln3+
ion with organic ligand can lead to a system capable of
overcoming intrinsically low molar absorption
coefficients (typically 1-10 Mminus1cmminus1) of Ln3+ ions and
effectively transferring excited energy from the light-
absorbing ligand to central Ln3+ ion This sensitization
process is much more effective than the direct excitation
of Ln3+ ions To date it is well-believed that only energy
transfer from the triplet state of luminescent ligands to
Ln3+ ion is the most dominant mechanism Therefore
most researches toward lanthanide ion sensitizers have
been focused on developing the luminescent ligands with
a triplet state matching the receiving lanthanide ion
energy levels Interestingly however several reports
mentioned the energy transfer from the excited singlet
state to Ln3+ ion Very recently we also reported all
possible ET pathways using Pt-porphyrin (ETt) and
anthracene ligand (ETs) and additionally demonstrated
the unusual ET pathway through the intramolecular
charge transfer (ICT) state of the naphthalene ligand to
Ln3+ ion (ETc) for the first time (see Scheme 1)
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
N A -X
Fluor
Phosph
8S 72
6P 72
G d 3 +
1530 nm
4I132
4I112
4I92
4F92
4F72
4I15 2
4S3 2
2G 92
E r 3+
times
IS C
3O 2-quench
ET s
T1
S 1
C T
E TtE T c
Ligand
E
6P72
S0
Scheme 1 Three Possible Energy Transfer Pathways
toward the Efficient Lanthanide Emission
For finding out the most dominant ET pathway
toward the highly efficient Ln3+ emission the Ln3+
emission efficiency comparison for all three ET
pathways should necessarily be explored References (a) J B Oh M K Nah and H K Kim Adv Funct Mater 17(3) 413 (2007) (b) Y H Kim N S
Baek and H K Kim ChemPhysChem 7(1) 213( 2007) (c) M-K Nah H K Kim and J-G Kang etal J Phys
Chem A 111(28) 6157 (2007) (d) N S Baek M K Nah Y H Kim and H K Kim Bull Korean Chem Soc
27 1729(2006) (e) N S Baek Y H Kim and H K Kim Adv Funct Mater 16 1873 (2006)
Hwan Kyu Kim b 1957 in Ulsan Korea Univ of Ulsan (BS 1980) KAIST (MS 1982)
Carnegie Mellon Univ (PhD 1990 Prof K Matyjaszewski) Cornell Univ (Postdoc 1991-
3 Prof C K Ober) ERTI (Senior Researcher 1993-4) Hannam Univ (Professor 1994-
2007) Korea Univ (Professor 2007-) Research fileds luminescent lanthanide materials
low-loss polymeric waveguide materials dye-sensitized solar cell organicinorganic hybrid
materials for photonic applications and organic optoelectronic materials for OLED
18
O-17
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Ruthenium Sensitizers for All-Purpose Dye-Sensitized Solar Cells
Chun-Guey Wu Department of Chemistry National Central University
Jhong-Li Taiwan 32001 ROC Abstract Dye-sensitized solar cell (DSC) is the third generation photovoltaic device with great potential
for transforming solar heat to electricity Amongst the five components Anode TiO2 electrode Dye Electrolyte and Cathode which were assembled to the DSC devices dye molecules can be regarded as one of the heart components In the talk I will introduce the molecular engineering for high efficiency ruthenium-based dyes prepared in our laboratory The molecular design of the ruthenium complexes for various types (solution state flexible and solid state) of DSC devices was demonstrated and the effect of the structureproperties of the dye on the photovoltaic performance of the corresponding DSC will be discussed
Keywords DSC ruthenium complexes ancillary ligand References
1 Chia-Yuan Chen Mingkui Wang Jheng-Ying Li Nuttapol Pootrakulchote Leila Alibabaei Cevey-ha Ngoc-le Jean-David Decoppet Jia-Hung Tsai Carole Graumltzel Chun-Guey Wu Shaik M Zakeeruddin and Michael Graumltzel ACS Nano 2009 3 3103-3109
2 Kun-Mu Lee Shi-Jhang Wu Chia-Yuan Chen Chun-Guey Wu Masashi Ikegami Kozo Miyoshi Tsutomu Miyasaka and Kuo-Chuan Ho J Mater Chem 2009 19 500-5015
3 Chia-Yuan Chen Jian-Ging Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Kuo-Chuan Ho Angew Chem Int Edit 2008 47 7342 ndash7345
4 Chia-Yuan Chen Shi-Jhang Wu Jheng-Ying Li Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Mater 2007 19 3888-3891
5 Chia-Yuan Chen Hung-Chieh Lu Chun-Guey Wu Jian-Ging Chen Kuo-Chuan Ho Adv Funct Mat 200717 29-36
6 Chia-Yuan Chen Shi-Jhang Wu Chun-Guey Wu Jian-Ging Chen and Kuo-Chuan Ho Angew Chem Int Edit 2006 45 5822-5825
19
O-18
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Electrical doping in organic semiconductors display and other applications
Jang-Joo Kim
Department of Materials Science and Engineering Seoul National University Seoul jjkimsnuackr
Tremendous progress in inorganic semiconductor devices
must not be possible without the development of n- and
p-dopants to control the electrical properties of the
semiconductors It is only recently however that
electrical doping in organic semiconductors has attracted
attention to reduce the contact resistance and increase the
conductivity of organic semiconductors and to reduce the
driving voltage of the organic devices Hetero-junctions
made of different materials without doping rather than
homo-junctions with p- or n-dopants have been used for
multilayer organic semiconductor devices Since the
materials are intrinsic with low mobility and low free
carrier density the devices need high voltage to drive
Recently we have developed new electrical dopants
of rhenium oxide (ReO3) and cupper iodide (CuI) as p-
dopants and rubidium carbonate (Rb2CO3) as an n-dopant
respectively ReO3 has advantage of low temperature
evaporation (about 300degC) with enhanced device stability
Various kinds of high performance organic light emitting
diodes have been realized including bottom emission
green phosphorescent p-i-n LEDs [1] tandem OLEDs [2]
top-emission OLEDs [3] and White OLEDs Organic
solar cells using the p and n-doped charge transporting
layers and tandem OPVs will also be presented
The charge generation efficiency of p-dopants by
doping in host materials has been evaluated by optical
and electrical methods to relate the energy levels of the
dopants and host materials CuI MoO3 and ReO3
having different work functions were doped in different
hole transporting organic materials Formation of charge
transfer (CT) complexes increases linearly with
increasing doping concentration for all the dopants
Dopants with higher work function (ReO3gtMoO3gtCuI)
are more effective in the formation of CT complexes
and in the generation of the charges in the doped films
[4] Mobilities of carriers were reduced when organic
semiconductors are heavily doped [5] which is different
from the previous reports This controversy will be
discussed in the presentation
References [1] Dong-Seok Leem et al Appl Phys Lett 91 (2007) 011113 [2] Jae-Hyun Lee Dong-Seok Leem
Jang-Joo Kim Organic Electronics 9 (2008) 805 [3] Dong-Seok Leem et al Appl Phys Lett 93 (2008) 103304
[4] Jae-Hyun Lee Appl Phys Lett 94 (2009)123306 [5] Jae-Hyun Lee et al Organic Electronics in print
Jang-Joo Kim b in Korea Seoul National University (BS 1977) Stanford University (PhD 1987 Prof D A
Stevenson) SRI International (Postdoc rsquo86-lsquo87) Electronics and Telecommunications
Research Institute (principal member of technical staff 1987) Professor Gwangju Insitute of
Science and Technology (1997) Professor Soul National University (2003) Research fields
organic materials and device for electronic and photonics
20
O-19
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Photophysics and Photochemistry of Blue Green and Red Phosphorescent Triscyclometalated Ir(III) Complexes
Takashi Karatsu
Department of Applied Chemistry and Biotechnology Graduate School of Engineering Chiba University Japan
karatsufacultychiba-ujp
Phosphorescent materials have attracted much attention as the material for the organic light emitting diode (OLED) because of their high performance of electroluminescence Especially iridium (III) triscyclometalated complexes are just started fabricating displays after pioneering works by the Thompson and Forrest group Research interests have been focused on the facial (fac) isomer that is easier to synthesize and has higher phosphorescence quantum yield (Φp) and stronger chemical stability than those of meridional (mer) isomer However little is known about the mer isomer Thompson group and we have reported merrarrfac photochemical one-way geometrical isomerizationa-
c Recently it is shown that synthetic importance of the mer-isomer that is synthesizable under mild condition to make fac-isomer of thermally unstable complexes through photoisomerization It has been reported
that presence of mer-isomer quenches fac-isomer phosphorescence however several pure mer-isomers have been shown to be useful to fabricate OLED devices
Here we would like to report mechanism and reaction state of merrarrfac photochemical geometrical isomerization investigated for the several blue green and red phosphorescent iridium (III) triscyclo-metalated complexes shown below Our investigations are based on the experiment in solution and quantum chemical calculations Recently the excited states involved in the nonradiative deactivation of fac-isomer are clarified to be similar states involved in the isomerization of mer-isomer In addition to the geometrical isomerization we have investigated how ΔminusΛ chirality is involved in the merrarrfac geometrical isomerization to elucidate detail mechanismd
References (a) Tamayo A B Alleyne B D Djurovich P I Lamansky S Tsyba I Ho N N Bau R Thompson M E J Am Chem Soc 2003 125 7377-7387 (b) Karatsu T Nakamura T Yagai S Kitamura A Yamaguchi K Matsushima Y Iwata T Hori Y Hagiwara T Chem Lett 2003 32 886-887 (c) Karatsu T Ito E Yagai S Kitamura A Chem Phys Lett 2006 424 353-357 (d) Tsuchiya K Ito E Yagai S Kitamura A Karatsu T Eur J Inorg Chem 2009 2104-2109
Takashi Karatsu b 1958 in Nagano Japan University of Tsukuba (BS 1981 PhD 1986
Prof K Tokumaru) University of Utah University of Texas at Austin (Postdoc 1986 Prof
J Michl) University of Tsukuba (Research Associate 1988) Chiba University (Lecturer
1989 Assistant Professor 1991 Professor 2005) Research fields Photochemistry Reaction
mechanism Fluorescent and phosphorrescent materials Organosilane chemistry
Photopolymer Cis-trans isomerization of olefin
21
O-20
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Random Lasing Films with Organic- Inorganic- Composites
Yong-Rok Kim
Department of Chemistry Yonsei University Republic of Korea yrkimyonseiackr
Since the first observation of a laser-like emission in
disordered medium great attentions have been given to
the investigation of random lasing phenomena due to the
possible applications of small-sized active elements in
photonic devices A random lasing is different from a
conventional lasing since it does not require any cavity
mirrors in its feedback mechanism The feedback process
in a random lasing is provided by optical scatterings in
disordered media and therefore random lasing can be
observed in all directions due to the randomly located
optical cavities
In this presentation two different types of random
lasing films are introduced Confined nanofiber
composite within nanoporous alumina membrane(PAM)
and electrocoated film with charged optical particles
The directional random lasing was firstly demonstrated
with the PAM which was filled with hybrid polymer
which consisted of poly(N-vinylcarvazole) (PVK)
Rhodamine 6G and TiO2 nanoparticlesa The angle-
resolved photoluminescence (PL) measurement
suggested that lasing had a strong directionality along the
hybrid polymer nanowires which were embedded within
the nanochannels of the PAM Although wavelengths of
the lasing peaks were not affected by excitation and
detection angles lasing behavior strongly depended on
the pore diameters of the PAMs utilized
Charged optical paticles were utilized to demonstrate
random lasing with the electro-coated film on ITO grassb
The film was consisted of the multi layer charged silicate
nanoparticles covalently bonded with the dyes The
thickness of the random lasing film was controlled with
different electric fields The strong dependence of lasing
pattern on the thickness of the film was due to the beam
penetration dept and the different pattern of the closed
loop As expected it was observed that the lasing
threshold was decreased with the increased thickness of
the film Unique feature of this film with charged optical
nanoparticles will provide the well controlled patterns of
random lasing by utilizing the electric field
References (a) H-W Shin S-Y Cho K-H Choi S-L Oh and Y-R Kim Appl Phys Lett 2006 88 263112 (b) H-
W Shin S-L Oh L Galmiche B Lama P Audebert Y-R Kim Surf Coat Tech 2009 submitted
Yong-Rok Kim Yonsei University (BS 1982) (MS 1984) University of Pennsylvania (PhD
1991 Prof R M Hochstrasser) (Postdoc 1991-1992) Professor Dept of Chemistry Yonsei
University Republic of Korea (1993-present)
Research fields photon applied functional nanocomposites ultrafast laser spectroscopy
functional energetics with morphology control photocatalytic nanoporous membranes medicinal
chemistry of singlet oxygen dynamics
22
O-21
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Toward High Efficiency Polymer-Nanoparticle Hybrid Solar Cell
Wei-Fang Su Department of Materials Science and Engineering National Taiwan University
1 Roosevelt Road Sec 4 Taipei Taiwan Emailsuwfntuedutw
Hybrid materials made from conducting polymer-nanoparticle are attractive for solar cell because of the prospect of light weight low cost high throughput high energy density using reel-to-reel or spray deposition on flexible substrate
In this research we are investigating thermal stable polymer-metal oxide hybrid material for solar cell We are able to greatly improve the efficiency of the hybrid solar cell by fabricating highly ordered nano structure hybrids studying the morphology and interlayer characteristics of hybrid and modifying the surface of metal oxide The device usually has the construction of ITOPEDOThybridAl four layers The inclusion of TiO2 nanorods into MEHPPV conducting polymer that increases the ordering of polymer and its absorption spectrum was red shifted the exciton life has been decreased to less than half of the neat polymer (2006 Nanotechnology 17 5781-5785) The efficiency of MEHPPV-TiO2 solar cell can be increased by 25 times by inserting a TiO2 nanorod layer between the hybrid active layer and Al electrode due to the enlargement of the interconnecting network between the hybrid and electrode (2006 Nanotechnology 17 5387-5392) The carrier mobility can be increased by 9 times using column structured ZnO electron transport layer infiltrated with the P3HT-TiO2 hybrid due to efficient charge transport (2007 J Mater Chem 17 4571-4576) The effect of polymer molecular weight on the nanoscale morphology that related to the performance of P3HT-TiO2 hybrid solar cell was studied by scanning near field optical microscopy (SNOM) atomic force microscopy (AFM) and confocal Raman microscopy The results are correlated well with the carrier transport behavior of different molecular weight polymer investigated by the time-of-flight technique (2008 J Mater Chem 18 4097ndash4102) The solar cell fabricated from surface modified TiO2 nanoparticles with bandgap tuned linker and P3HT hybrid has achieved the relatively high power conversion efficiency of 22 under simulated AM 15 illumination (100 mWcm2) (2008 Appl Phys Lett 92 053312 2009 J Am Chem Soc131 3644 )
The efficiency of the device is expected to be further improved by using newly developed self assembled highly ordered nano structure copolymers of P3HT-P2VP (2007 J Am Chem Soc 129(36) 11036-11038) and low bandgap conducting copolymers (2007 Macromolecules 40 8189-8194 and 2008 Macromolecules 41 6664-6671) This project is supported by the National Science Council of Taiwan (95-3114-P-002-003-MY3) and the AOARD of US Air Force (AOARD-07-4014)
23
O-22
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Solid-State NMR Analysis of Materials for Organic Light-Emitting Diodes
Hironori Kaji Institute for Chemical Research Kyoto University Uji Kyoto 611-0011 JAPAN
e-mail kajisclkyoto-uacjp
Organic light-emitting diodes (OLEDs) are promising devices for future applications of large area displays and room lighting The clarification of the structure and dynamics of organic materials in OLEDs is important to understand the device performances and to obtain the guiding principles for the material designs for OLEDs with excellent properties However the detailed analyses of the structure and dynamics of OLED materials have not yet been carried out
Under the circumstances we are now attempting to carry out the precise analyses of OLED materials using state-of-the-art solid-state NMR methodologies The NMR methods enable us to precisely analyze the local structure of the material not only in the crystalline state but also in the disordered state including the amorphous state Precise dynamics analyses are also possible by solid-state NMR In this presentation we focus on the solid-state NMR characterization of the two OLED materials tris(8-hydroxyquinoline) aluminum(III) (Alq3) and NNrsquo-diphenyl-NNrsquo-di(m-tolyl)benzidine (TPD) which are a widely used light-emitting electron-transport material and a widely used hole-transport material respectively
Figure 1 shows an example of solid-state NMR experiments for Alq3 The fluorescence wavelengths of Alq3 depend on the structures The difference of the isomeric states or that of the intermolecular interactions is considered to be the origin however the problem has been still under debate Two-dimensional double-quantum (2D DOQSY) solid-state NMR experiments can correlates the relative orientations of the ligands therefore the distinction of the meridional and facial isomers will become obvious The 2D DOQSY spectra of the isotopically 15N-labeled Alq3 in the - amorphous- and -Alq3 in Fig 1 clearly show that the - and amorphous-Alq3 are composed of the meridional isomer whereas -Alq3 is composed of the facial isomer In sharp contrast with the yellowish green emission from - and amorphous-Alq3 -Alq3 emits blue luminescence It is found from the above 2D DOQSY experiments that the emission wavelengths are determined by the isomeric states of Alq3
Hironori Kaji 梶 弘典 b 1965 in Kobe Japan Kyoto Univ (BS 1989 MS 1991 Ph D 1994 Prof N Soga) Assistant Prof Kyoto Univ (1994) Univ Massachusetts (Visiting Scientist 1998-1999 Prof K Schmidt-Rohr) JST PRESTO researcher (2002-2006) Associate Prof Kyoto Univ (2003) Professor (2009-) Research filed solid-state NMR organic light-emitting diodes (OLEDs) quantum chemical calculations chemistry for organic amorphous materials
Fig 1 Experimental 15N 2D DOQSY spectra of (a) - (b) amorphous and (c) -Alq3 The best-fit spectra are shown at the corresponding lower column (d) ndash (f)
24
O-23
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Gearing of Molecules for Highly Correlated Molecular Packing
Hsiu-Fu Hsu Hsin-An Lin Hsiu-Hui Chen Yi-Hsiang Chan and Yi-Shian Yeh Department of Chemistry Tamkang University Tamsui Taiwan
e-mail hhsumailtkuedutw Physical properties of active organic materials strongly depend on molecular correlations materials Columnar liquid crystalline materials continuously attract interests because of their cooperative physical properties that lead to many technological applications Herein by molecular design two organic systems exhibiting high intermolecular correlations by gearing of molecules are reported In the first system by installing an additional alkoxy chain on each sidearm in the well studied discotic nematogen hexakis(4-alkoxylphenylethynyl)benzene a series of compounds exhibiting a columnar mesophase with low melting temperatures and wide liquid crystal ranges were achieved The structural modification has resulted in a favored molecular swirl arrangement ie molecular rosette geometry evidenced by scanning tunnelling microscopy In addition to various known intermolecular interactions cooperative interactions of molecular swirls with the same rotational sense within and among columns are attributed for the formation of a columnar mesophase with a wide temperature range The lateral addition of the chains with respect to each side-arm has resulted in low melting points In the second system helicenes derived from hexabenzocoronene were designed to avoid disc sliding within columns
ROOR
OROR
OR
OR
OROR
ORRO
RO
RO
gearing of molecular swirls References [1] Chien S-C Chen H-H Chen H-C Yang Y-L Hsu H-F Shih T-L Lee J-J Adv Funct Mater
2007 17 1896-1902 [2] Lee S-L Lin H-A Lin Y-H Chen H-H Chan Y-H Chu Y-C Hsu H-FChen C-hLee J-
JWu C 2009 submitted
Hsiu-Fu Hsu 徐秀福 b 1966 in Taipei Taiwan National Sun Yat-Sen Univ (BS 1988) Univ of Illinois at Urbana-Champaign (PhD 1997 Prof J R Shapley) Massatusettes Institute of Technology (Postdoc 1997-1999 Prof T M Swager) Assistant Prof (1999-2004) Associate Prof (2004-2007) Professor (2007-) Research filed organometallic chemistry liquid crystal chemistry nano materials self-assembled monolayers
O-24
25
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Functional Metallophosphors as Robust OLED Materials for Effective Charge Carrier InjectionTransport
Wai-Yeung Wong
Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong rwywonghkbueduhk
Organic light-emitting diodes (OLEDs) show great
promise of revolutionizing display technologies in the
scientific community Heavy transition metal complexes
have recently gained tremendous academic and industrial
research interest for fabricating highly efficient
phosphorescent OLEDs by taking advantage of the 13
exciton singlettriplet ratio predicted by simple spin
statistics Traditional room-temperature phosphorescent
dyes are monofunctional materials working only as light-
emitting centres but other key issues including charge
generation and transport remain to be addressed in the
electroluminescence
This talk highlights recent advances in developing
new synthetic strategies for multifunctional
organometallic phosphors which integrate both
luminescent and charge carrier injectiontransport
functions into the same molecules so that they perform
most if not all of the necessary functional roles (viz
photoexcitation charge injection and transport as well
as recombination) for achieving high-efficiency devices
Considerable focus is placed on the design concepts
towards the tuning capability of phosphorescence
emission color of this prominent class of
metallophosphors
N OIr
O
PO
N OIr
O
O
N OIr
O
S OO
N OIr
O
S
N OIr
O
N
N OIr
O
B
N OIr
O
Ge
N OIr
O
Si2 2 2
2 2 2 2
2
400 500 600 700
00
02
04
06
08
10
Wavelength (nm)
EL
inte
nsity
(a
u)
N
O
PtOO
Ge
NPt
OO
References (1) G-J Zhou C-L Ho W-Y Wong Q Wang D-G Ma L-X Wang Z-Y Lin T B Marder and A
Beeby Adv Funct Mater 2008 18 499 (2) G-J Zhou W-Y Wong B Yao Z-Y Xie and L-X Wang Angew Chem
Int Ed 2007 46 1149 (3) W-Y Wong C-L Ho Z-Q Gao B-X Mi C-H Chen K-W Cheah and Z Lin Angew
Chem Int Ed 2006 45 7800 (4) W-Y Wong and C-L Ho Coord Chem Rev 2009 253 1709 (5) W-Y Wong and
C-L Ho J Mater Chem (Feature article) 2009 19 4457
Wai-Yeung Wong (Raymond 黃維揚) b 1970 in Hong Kong The University of Hong Kong
(BSc 1992 PhD 1995 Prof W-T Wong) Texas A amp M University (Postdoc 1996 Prof F A
Cotton) University of Cambridge (Postdoc 1997 Profs The Lord Lewis and P R Raithby)
Assistant Prof (1998minus2003) Associate Prof (2003minus2007) Professor (2007minus) Hong Kong Baptist
University Research fields synthetic inorganic and organometallic chemistry novel molecular
functional materials and metallopolymers for OLEDPLED and organic solar cell applications
nonlinear optics and nanotechnology
26
O-25
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Study of Top ITO Electrode Formation for Inverted Top Emission OLED
MunPyo Hong
Dept of Display Semiconductor Physics Korea University Chungnam 339-700 KOREA
The Inverted Top emission OLED (ITOLED) is most
suitable structure for high efficiency OLED display with
n-type TFT based backplane However ITO thin film
deposition process on organic semiconductor for anode
electrode formation is one of the most problematic
processes to realize the ITOLED because the sputtering
process causes critical damages on underlying organic
layers by highly energetic charged particles UV radiation
and heating-up To salve the limitations of plasma
sputtering process we are developing the Neutral Beam
Assisted (NBA) ITO sputtering system as a plasma
damage free process at room temperature For evaluating
the low damage abilities of our NBA ITO sputter we
have developed ITOLED test cells with Al cathode Liq
Alq3 NPB transition metal oxide HIL test ITO anode
structures(a) While fabricating the test cells the ITO
layers are prepared by normal DC sputtering or NBA
sputtering for the purpose the experiments Base on the
results of the OLED test cells the NBA ITO sputtering
system can be verified that inducing almost no damages
on the underlying organic semiconducting layers(b) Also
we have investigated the role of the transition metal
oxide HILs (WO3 MoO3 V2O5) as a protection layer
against plasma damages during ITO deposition by
plasma sputter after exposure to Ar plasma the change
of electrical optical properties of the transition metal
oxide layer were measured and the change of
composition structures were also analyzed by XPS In
the case of WO3 thin layer the Ar plasma exposing
effect could cause the formation of non-stoichiometrics
so that change the band gap state Consequently these
thin metal oxide layers with thickness of about 5 nm
could not be appropriate to protect underlying organic
layers against plasma attacks
1 1010-6
10-4
10-2
100
102
104
ITO
NPB
Al
Glass
WO3
(a)
No Plasma Treatment DC Power 40W DC Power 120W DC Power 200W
Cur
rent
den
sity
(m
Ac
m2 )
Voltage (V)
References (a) YouJong Lee JooHyung Kim J N Jang MunPyo Hong Thin Solid Films 2009 517 4019ndash4022
(b) YouJong Lee JooHyung Kim Soonnam Kwon MunPyo Hong Organic Electronics 2008 9 407ndash412
MunPyo Hong 1963 in Korea Hanyang University (BS 1987) University of Wisconsin-Madison (PhD 1995) University of Wisconsin-Madison (Research Assistant 199206~199505) Center of Plasma Added Manufacturing U of Wisconsin-Madison (Research Associate 199505~199511) Samsung Electronics LCD RampD Center (Principal Engineer Group Leader Project Manager 199512~200601) Sungkyunkwan University (Joint Professor 200003~200506) Korea University (Professor 200602~Present)
Research fields flexible display plasma process organic electronic device (OTFT OLED) inorganic TFTs e-paper
-12 -8 -4 0 4 8 12 16 20 2410-510-410-310-210-1100101102103
Normal IBOLED NBAS ITO Deposited IBOLED DC Sputtering ITO Deposited IBOLED
Voltage (V)
Cur
rent
den
sity
(m
Ac
m2 )
27
O-26
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Novel Fullerene Derivatives and Printed Organic Solar Cells
Changjin Lee
Adv Meter Div KRICT Daejeon Korea cjleekrictrekr
Low cost solar energy conversion using the mixture of
conjugated polymeric materials and acceptors has
become getting feasible through the development of
organic ldquobulk heterojunctionrdquo structure where efficient
light-induced charge separation is enabled by a large
area donor-acceptor interface Printing with solution of
P3HT and PCBM is possible using inkjet printer and
suggested a way to manufacturing low cost and large
area organic solar cells This kind of semiconducting
inks will be considered as new concept for the fusion
technology of the chemical and electronic industry
We have synthesized novel 13-diketone modified
C60s fluorinated alkoxy substituted methanofullerenes
(PCBFs) ethyleneoxy group substituted
methanofullerenes (PCBEs) as acceptor materials in
OPVCs OPVCs fabricated by using the mixture of
P3HT and mono-13-diketone modified fullerene as an
active layer showed excellent power conversion
efficiency of 342 after annealing at 160 ordmC for 15
min Some of the structures of new fullerenes were
shown in Figure 1 Also we had prepared ink-jetted
organic solar cell made of P3HT-PCBM and observed
42 of photoconversion efficiency Results of printed
organic solar cells using printed PEDOTPSS layer Ag
electrode and aerosol-jet printer will be discussed
References (a) H S Lee S C Yoon J Lim M Lee and C Lee J Nanosci Nanotech 8 4533 (2008) (b) S H Eom
S Senthilarasu P Uthirakumar S C Yoon J Lim C Lee H S Lim J Lee S-H Lee Org Electr 10 536 (2009)
Changjin Lee b 1959 in Daegu Korea Seoul National U (BS 1981 Ms 1983) U of
Minnesota (PhD 1989 Prof Paul G Gassman) U Texas (Postdoc 1991 Prof M
Fox) Principal Research Scientist KRICT Director of Device Mater Res Center
(2008)
Research fields synthesis and fabrication of organic semiconductors printed devices
00 02 04 06 08 10 12 14 16 18 20 22-10
-08
-06
-04
-02
00
02
04
Cur
rent
(mA
)
Voltage (V)
1-cell 2-cells 3-cells
28
O-27
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Highly Efficient Dye-Sensitized Solar Cells based on Porphyrin
Sensitizers and One-dimensional TiO2 Nanostructures
Eric Wei-Guang Diau
Department of Applied Chemistry and Institute of Molecular Science National Chiao Tung
University Hsinchu 30010 Taiwan E-mail diaumailnctuedutw
This lecture will give brief introduction for a new series of porphyrin dyes together with the
improvement of the cell performance using one-dimensional (1D) TiO2 nanostructures For the new dyes we have designed a series of novel zinc porphyrin sensitizers with the structures containing push-pull group porphyrin core phenylethylnyl bridge and carboxylic acid anchor We found that the cell performance of the porphyrin-based dye-sensitized solar cell (DSSC) is similar to that made of the N719 dye making this series of porphyrins a promising candidate for colorful DSSC applications [1] For the electron-transport layer it has been pointed out that the electron transport in a traditional nanoparticulate (NP) DSSC device is a limiting factor to achieve higher light-to-electricity conversion efficiency due to the structural disorder at the contact between two TiO2 NPs To improve the charge-collection efficiency by promoting faster electron transport and slower charge recombination we have made the TiO2 films constructed of either 1D nanorods (NR) or oriented nanotube (NT) arrays [2] The cell performances of the corresponding devices are presented together with the rational electron-transport kinetics Measurements of femtosecond fluorescence up-conversion [3] were carried out to evaluate the electron-injection yields of the porphyrinTiO2 films with control experiments conducted on porphyrinAl2O3 films under the same experimental conditions
References [1] (a) C-W Lee H-P Lu C-M Lan Y-L Huang Y-R Liang W-N Yen Y-C Liu Y-S Lin E W-G Diau and
C-Y Yeh Chem Eur J 2009 115 1403 (b) H-P Lu C-L Mai C-Y Tsia S-J Hsu C-P Hsieh C-L Chiu
C-Y Yeh and E W-G Diau Phys Chem Chem Phys communication 2009 11 10270
[2] (a) C-C Chen H-W Chung C-H Chen H-P Lu C-M Lan S-F Chen L Luo C-S Hung and E W-G
Diau J Phys Chem C 2008 112 19151 (b) C-C Chen W D Jehng L-L Li and E W-G Diau J
Electrochem Soc 2009 156 C304
[3] (a) C-Y Lin C-F Lo L Luo H-P Lu C-S Hung and E W-G Diau J Phys Chem C 2009 113 755 (b) C-
W Chang L Luo C-K Chou C-F Lo C-Y Lin C-S Hung Y-P Lee and E W-G Diau J Phys Chem C
2009 113 11524 (c) H-P Lu C-Y Tsai W-N Yen C-P Hsieh C-W Lee C-Y Yeh and E W-G Diau J
Phys Chem C 2009 113 20990
29
O-28
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Novel Approaches for Enhancing Temporal Alignment Stability of Second-Order Nonlinear
Optical Polymers
Su Hwan Bae Sin Tae Kim Dongsu Kim and Tae-Dong Kim
Department of Advanced Materials Hannam University Daejeon 305-811 Korea Email tdkimhnukr
Poled organic electro-optic (EO) materials have
enabled many advances in the exploration of high-speed
and broadband information technologies Polymer-based
EO devices have been demonstrated to have large
bandwidths over 110 GHz low driving voltages and
sustain their performance in a flexible form or under
extreme environmental conditions They have also been
utilized for the generationdetection of a gap-free pulsed
THz system with a bandwidth up to ~12 THz
A major breakthrough in the area of organic EO
materials has been recently achieved To go beyond the
oriented gas model limit for organic EO materials new
approaches of using nanoscale architecture control and
supramolecular self-assembly have been proved as a very
effective method to create a new paradigm for materials
with very exciting properties High-performance EO
polymers were demonstrated by a facile and reliable
Diels-Alder ldquoclickrdquo reaction for postfunctionalization
and lattice hardening to improve EO activity (r33) and
thermal stability This type of ldquoclickrdquo chemistry paves
the way to systematically study the relationship among
EO activity chromophore shape and number density of
the chromophores With these novel approaches we
succeeded in enlarging the full potential of organic NLO
materials by a factor of 3~5 and developing a variety of
nano-structured organic EO materials with ultrahigh r33
values and excellent auxiliary property such as thermal
stability and optical transparency The availability of
such high r33 values enables not only unprecedented
performances in conventional device formats but also
the development of new devices such as hybrid
modulators and EO polymers integrated with silicon
photonics
N
OSi O
CNNCNC
CF3
N
N
N
N
O
O
O O
O
O
N
N
N
N
O
O
O O
O
O
TMI
6
OO
OO 012080
OO 008
N OO N
O
O
S O
OCF3
NCNC
CN
OO
O
FF
F
FF
F
FF
F
F
24
PassiveCrosslinker
Guest Chromophore Side-chain EO polymer
Poling
Crosslinked EO Polymerwith binary chromophores
Blends of PM-AJL04 6 and TMI
Lattice hardening
24
Figure 1 A crosslinked NLO polymer in-situ generated by
Diels-Alder reaction in a side-chain NLO polymer with binary
chromophores
References (a) T-D Kim J Luo L R Dalton A K-Y Jen et al J Phys Chem C 112 (2008) 8091 (b) T-D Kim J
Luo L R Dalton A K-Y Jen et al J Am Chem Soc 129 (2007) 488 (c) T-D Kim J Luo A K-Y Jen et al Adv
Mater 18 (2006) 3038
Tae-Dong Kim b 1972 in Seoul Korea Hannam Univ (BS 1998) Hannam Univ (MS 2000) Univ
of Washington (PhD 2007 Prof A K-Y Jen) Hannam Univ (Assist Prof 2008 - ) Research fileds
Nonlinear optical materials organic and polymeric semiconductors low band-gap polymers for solar
cells
30
O-29
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Poster Presentation
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Synthesis and Optical Properties of Perylene Bisimide and Anthracene Derivatives for Optoelectronic Materials
Po-Jen Ku 1 I-Lin Lee 2 Shih-Sheng Sun 1
1 Institute of Chemistry Academia Sinica Taipei
2 National Taiwan University of Science and Technology Taipei
E-mail sssunchemsinicaedutw An electron withdrawing ethynyl-benzimidazole derivatives attached to 17-bay position of NNrsquo-bis(2-ethyl-hexyl)perylene-34910-bis(dicarboximide) (QC series) or attached to 910-position of anthracene (QA and QB series) has transformed these molecules to n-channel organic field-effect transistor (OFET) materials UV-Vis absorption specra displayed bathochromic shift of these molecules owing to the electron-withdrawing effect TGA also revealed good thermal stability OTS-treated OFET devices showed low electron mobility and IonIoff
R
R
R1 = CHO
N
HN
N
HN CN
CN
NNC12H25
NNC12H25 CN
CN
R2 =
R3 =
R4 =
R5 =R = 1 2 4 5
RR = 1 2 3
NN
O
O
O
O
R
RR = 1 2 4 5
QA series QB series QC series
0
05
1
300 350 400 450 500 550 600
wavelength nm
norm
aliz
ed a
bs
0
05
1
norm
aliz
ed e
mis
sion
QB-1
QB-2
QB-3
4-(anthracen-9-ylethynyl)benzonitrile
0
02
04
06
08
1
12
300 400 500 600 700 800 900 1000 1100
wavelength nm
norm
aliz
ed a
bs
0
02
04
06
08
1
12
norm
aliz
ed in
tens
ity
QC-1-UV-EMQC-2-UV-EMQC-4-UV-EMQC-5-UV-EM
References
[1] Brooks A Jones Antonio Facchetti Michael R Wasielewski Tobin J Marks J Am Chem
Soc 2007 129 15259-15278
[2] Sakamoto Y Suzuki T Kobayashi M Gao Y Fukai Y Inoue Y Sato F Tokito S J
Am Chem Soc 2004 126 8138
31
P-1
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Dibenzo[fh]thieno[34-b]quinoxaline-Based Small Molecules for Efficient Bulk-Heterojunction Solar Cells
Marappan Velusamya Ying-Chan Hsua Jen-Hsien Huangb Hsien-Hsin Choua Kuo-Chuan Hob
Pei-Lun Wua Wei-Hau Changa Jiann T Lina and Chih-Wei Chuc
aInstitute of Chemistry Academia Sinica Nankang Taiwan
bDepartment of Chemical Engineering National Taiwan University Taiwan
cResearch Center for Applied Sciences Academia Sinica Nankang Taiwan
E-mail jtlinchemsinicaedutw gchugatesinicaedutw
Two isomeric compounds (1 and 2) containing an electron deficient dibenzo[fh]thieno[34- b]quinoxaline core and two peripheral arylamines were synthesized and characterized Besides intense πminusπ transition the charge-transfer transition in these compounds also contributes to light harvesting Solution processed bulk heterojunction (BHJ) solar cells based on these sensitizers and [66]-phenyl-C61-butyric acid methyl ester (PCBM) are reported The performance of the cells depends on the solvent used for fabrication and the ratio of the compound vs PCBM The cell fabricated from 167 wt PCBM exhibited a high power conversion efficiency of 170 and the external quantum yield of 55 The film of the cell was found to have balanced electron and hole mobility and good film morphology
NN
S
NSN S
32
P-2
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Structurally Simple Dipolar Organic Dyes Featuring 13-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
Kuan-Fu Chen12 Ming-Chang P Yeh2 and Shih-Sheng Sun1
1Institute of Chemistry Academia Sinica 2Department of Chemistry National Taiwan Normal University
A series of structurally simple dipolar light-harvesting organic dyes featuring 13-cyclohexadiene in the aromatic π framework for dye-sensitized solar cells has been synthesized and characterized A model compound 16 was also synthesized for assessing the role of 13-cyclohexadiene played in the photovoltaic efficiency One obvious advantage of employing 13-cyclohexadiene unit in the framework of light-harvesting dyes is the essentially planar conformation in the structural skeleton which yields more dense packing of the dyes adsorbed on TiO2 surface not necessarily multilayer aggregation and therefore increases the amounts of dye loading on the surface The highest conversion efficiency of the DSSCs based on these dyes can reach up to 44
References [1] (a) Graumltzel M Nature 2001 414 338-344 (b) Hagfeldt A Graumltzel M Acc Chem Res 2000 33 69-277 (c) Robertson N AngewChem IntEd 2006 45 2338-2345 [2] OrsquoRegan B Graumltzel M Nature 1991 353 737-740 [3] (a) Kitamura T Ikeda M Shigaki K Inoue T Anderson N A Ai X Lian T Yanagida S Chem Mater 2004 16 1806-1812 (b) Satoh N Nakashima T Yamamoto K J Am Chem Soc2005 127 13030-13038
Kuan-Fu Chen 陳冠甫 b 1982 in Taipei Taiwan Chia Nan University of Pharmacy amp Science (BS 2002) National Taiwan Normal University (MS 2004) National Taiwan Normal University (Ph D 2006-) E-mail 895420065ntnuedutw
33
P-3
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Pure-hydrocarbon host materials for highly efficient green and red electrophosphorescent devices
Hao-Chun Tinga and Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwong ntuedutw
We designed and synthesized a series of indenofluorene derivatives with various pendant aryl
substitutions The molecular configurations engaged in these molecules can prevent detrimental
intermolecular interactions for suppressing aggregates and excimers formation These new
molecules exhibit high thermal and morphological stability and suitable triplet energies can serve as
pure hydrocarbon host materials for green and red phosphorescent OLED Devices incorporating
with InDSF and InF3-tt as host materials show the maximum EL quantum efficiency of 176 and
192 for green and red electrophosphorescence respectively In this symposium we will report
the physical properties X-ray structures and device characteristics
tol tol
toltol
InF3tt References 1 Merlet S Birau MWang Z Y Org Lett 2002 4 2157 2 Nicolas C Cyril P Joeumllle RB Freacutedeacuteric B Chem Eur J 2008 14 11328 ndash 11342 3 Jacob J Sax S Piok T List E J W Grimsdale A C Muumlllen K J Am Chem Soc 2004
126 6987 4 Damien Thirion Cyril P Freacutedeacuteric B Joeumllle RB Org Lett 2009 11 (21) pp 4794ndash4797
34
P-4
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
PhenylbenzimidazoleCarbazole-Based Bipolar Materials for Highly efficient Deep-Blue Fluorescence Green-yellow Phosphorescence Host and White OLEDs
Liang-Chen Chia Ken-Tsung Wonga Wei-Jiun Chenb and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
To whom correspondence should be addressed E-mail kenwongntuedutw
In this communication we report a new bipolar material (CPhBzIm) combined with phenylbenzimidazole and carbazole which was synthesized by Suzuki-Miyaura coupling reaction (Fig 1) CPhBzIm exhibits an excellent solid state photoluminescence quantum yield (QY= 69 ) high triplet energy (ET = 258 eV) and bipolar charge transport ability (μh μe ~10-5 cm2Vs) The multifunctional CPhBzIm was not only used to fabricate non-doped deep blue-emitting devices with promising performance (ηext = 3 CIE = 016 005) but also served as host material doped with 10 of Ir(pbi)2(acac) to realize green PhOLED (ηext= 192 ηp = 62 lmW CIE = 042 056)
Furthermore we have demonstrated a simple single-doped way to realize two-color based WOLEDs by use of the dual roles of CPhBzIm as both efficient blue-emitter and excellent host for green phosphor in the configuration ITOpedotDTAF (25 nm) CPhBzIm Ir(pbi)2(acac) 01 (25 nm) TPBI (50nm)LiFAl The white-emitting device exhibited a low turn-on voltage (25 V) and an luminance of 26500 cdm2 at115 V with CIE (031 033) its ηext reached 7 (155 cdA) at a luminance of 40 cdm2 The single-doped and single emissive layer device structure is much simple than the widely reported stacked multi-emissive-layer or triple doped WOLEDs [1]
Fig 1 Chemical structures of CPhBzIm and green phosphorescent dopant Ir(pbi)2(acac)
References [1] Y Tao Q Wang Y Shang C Yang L Ao J Qin D Ma and Z Shuai Chem Commun 77-79 (2009)
N
NN N
N
CPhBzIm
NN
Ir
2O
O
Ir(pbi)2(acac)
35
P-5
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
A spiro-configured ambiploar host material for impressively efficient single-layer green electrophosphorescent devices
Hsiao-Fan Chena Ting-Chih Wanga Ken-Tsung Wonga Hao-Chih Chiub and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan
b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan Department of Chemistry National Taiwan University Taipei 106 Taiwan
E-mail kenwongntuedutw 45-diazafluorene fused with 27-bis(carbazol-9-yl)fluorene into a spiro configuration give a bipolar molecule (CSC) that possesses a high triplet energy (ET = 265 eV) suitable energy levels (HOMOLUMO = 563236 eV) and balanced ambipolar carrier mobilities (μh μe ~ 10-6 cm2Vs) was successfully applied as an efficient host material compatible with various Ir-based green phosphors for realizing highly efficient single-layer PhOLEDs The best single-layer device comprised of (PPy)2Ir(acac) as the green emitter achieved a maximum ηext as high as 83 (314 cdA) at the practical brightness of 1000 cdm2 (8 V) and a maximum luminance of 140000 cdm2 driven at a current density of 1200 mAcm2 (175 V)
References 1 M-Y Lai C-H Chen W-S Huang J-T Lin T-H Ke L-Y Chen M-H Tsai C-C Wu
Angew Chem Int Ed 2008 47 581 2 Z Ge T Hayakawa S Ando M Ueda T Akiike H Miyamoto T Kajita M Kakimoto Chem
Mater 2008 20 2532 3 C-H Chen W-S Huang M-Y Lai W-C Tsao J T Lin Y-H Wu T-H Ke L-Y Chen
C-C Wu Adv Funct Mater 2009 19 2661 4 W-Y Hung T-C Tsai S-Y Su K-T Wong L-C Chi Phys Chem Chem Phys 2008 10
5822
36
P-6
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Highly Efficient CarbazoleOxadiazole-Based Bipolar Host Materials for Green Phosphorescent OLEDs
Shuo-Hsien Chenga Ken-Tsung Wonga and Wen-Yi Hungb
a Department of Chemistry National Taiwan University Taipei Taiwan b Institute of Optoelectronic Sciences National Taiwan Ocean University Keelung Taiwan
E-mail kenwongntuedutw
In this symposium we will report the synthesis physical properties and OLED applications of a series of carbazole-oxadiazole hybridized bipolar molecules cbzoxa mcpoxa and cbzdioxa (Fig 1) These novel molecules comprised of different number of donor and acceptor units exhibit promising physical properties suitable highest occupied molecular orbital and lowest unoccupied molecular orbital energy level (HOMOLUMO = ca 5722 eV) and high triplet energy (ET = 252 eV) Use these materials as host we fabricated highly efficient green eletrophosphorescent devices (ITOpedotDTAF (25 nm) host green phosphors (25 nm) TPBI (50nm)LiFAl) giving remarkable EL performance The maximum ηext can reach as high as 207 using cbzoxa as a host doped with green phosphor (PPy)2Ir(acac) (CIE = 034 062) All of the devices can be operated at relatively low turn-on voltage (~ 20 V) with high power efficiency (ηp max = 81 lmW)
N
N NO
N N
N NO
cbzoxa mcpoxa cbzdioxa
Fig 1 Chemical structures of cbzoxamcpoxa and cbzdioxa
37
P-7
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Polymer Light Emitting-Diodes Material Containing Unsymmetrical Substituted Group Synthesis and their Optical Electrochemical and Electrochromic
Properties Han-Yu Wua Kun-Li Wangb Der-Jang Liawa Kueir-Rarn Leec Juin-Yih Laic
a Department of Chemical Engineering National Taiwan University of Science and Technology 10607 Taipei Taiwan
b Department of Chemical Engineering and Biotechnology National Taipei University of Technology 10608 Taipei Taiwan
c RampD Center for Membrane Technology Department of Chemical Engineering Chung Yuan University 32023 Chung-Li Taiwan
E-mail liawdjmailntustedutw liawdjntuedutw A novel dibromo compound containing unsymmetrical substituted bi-triarylamine was
synthesized A conjugated polymer was prepared via the Suzuki coupling from the newly prepared dibromo compound and 99-dioctylfluorene-27-bis (trimethyleneboronate) The glass transition temperature (Tg) of the conjugated polymer was 140 oC 10 weight-loss temperatures (Td10) in nitrogen was 458 oC and char yield at 800 oC in nitrogen higher than 64 Cyclic voltammogram of the polymer film cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 070 and 110 V vs AgAg+ in acetonitrile solution The polymer films revealed excellent stability of electrochromic characteristics with a color change from yellow green of the neutral form to the dark green and blue of oxidized forms at applied potentials ranging from 0 to 13 V The color switching time and bleaching time were 425 s and 722 s for 860 nm and 551 s and 648 s for 560 nm
References [1] Liaw D J Wang K L Kang E T Pujari S P Chen M H Huang Y C Tao B C Lee K R Lai
J Y J Polym Sci Part A Polym Chem 2009 47 3880 [2] Liaw D J Wang K L Pujari S P Huang Y C Tao B C Chen M H Lee K R Lai J Y Dyes
and Pigments 2009 82 109 [3] Ling c Q D Liaw D J Zhu C X Chan D S H Kang E T Neoh K G Prog Polym Sci 2008 33 917 [4] Ling Q D Chang F C Song Y Zhu C X Liaw D J Chan D S H Kang E T Neoh K G J Am
Chem Soc2006128 8732
Der-Jang LIAW (廖德章)b 1947 in Taichung Taiwan National Cheng-Kung Univ(BS 1970) (Osaka University MS 1975 PhD 1978 Prof Nozakura and Kamachi) Associate Prof (1978) Professor(1982) Chair Professor (2008)
38
P-8
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Extended red light harvesting in a poly(3-hexylthiophene)iron disulfide nanocrystal hybrid solar cell
Di-YanWang1 Yun-Yue Lin2 Chun-Wei Chen2 Chia-Chun Chen13
1 Department of Chemistry National Taiwan Normal University Taipei Taiwan 2 Department of Materials Science and Engineering National Taiwan University Taipei Taiwan
3 Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan
Email cjchenntnuedutw
In the last decade polymer solar cells offered the opportunity for fabrication of low-cost large-area mechanically
flexible photovoltaic devices Semiconductor nanocrystals (NCs) have been incorporated into conjugated polymers to
form bulk heterojunction (BHJ) solar cells which consist of an electron-accepting network of nanocrystals formed
randomly within the polymer matrix (donor) Various semiconductor NCs have been used in polymerinorganic hybrid
solar cells such as (P3HT)CdSe nanorod P3HTTiO2 nanorod (MEH-PPV)PbS NC and P3HTPbSe NC hybrid
However the use of toxic elements such as Cd or Pb remains a limitation as the environmental issues need to be
addressedIn this paper we report a photovoltaic device based on a hybrid material consisting of P3HT and iron
disulfide (FeS2) NCs Iron disulfide (FeS2) which is a pyrite structure has a large optical absorption coefficient (60 times
105 cm-1) and a narrow bandgap of 095 eV The advantage in using the FeS2 NCs is because they are cheap abundant
and non-toxic The device based on P3HTFeS2 NC hybrid can exhibit an extended red light harvesting up to 900 nm
compared to the typical absorption edge of 650 nm of P3HT The increased photovoltaic response in the extended red
region of the P3HTFeS2 NC hybrid device provides a new method for fabricating low-cost and environmentally
friendly polymerinorganic hybrid solar cells
Reference [1] Ma W Yang C Gong X Lee K and Heeger A J Adv Funct Mater 2005 15 1617
[2] Li G Shrotriya V Huang J Yao Y Moriarty T Emery K and Yang Y Nat Mater2005 4 864
[3] Huynh W U Dittmer J J and Alivisatos A P Science2002 295 2425
[4] BeekW J E Wienk M M Kemerink M Yang X N and Janssen R A J 2005 J Phys Chem B 2005 109 9505
[5] Lin Y Y Chu T H Li S S Chuang C H Chang C H Su W F Chang C P Chu M W and Chen C W J Am Chem Soc2009 131
3644
[6] McDnoald S A Konstantatos G Zhang S Cyr P W Klem E J D Levina L and Sargent E H 2005 Nat Mater2005 4 138
[7] Cui D Xu J Zhu T Paradee G Ashok S and Gerhold M 2006 Appl Phys Lett 2006 88 183111
39
P-9
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Highly Stereoselectivity of Photoisomerization by Increasing Steric Hindrance of Inherent MOM-based Helicene Structure
Chien-Hsing Chen and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei
E-mail chefv043ntnuedutw
The helicene which dimethoxymethyl (MOM) dibenzosuberane (DBS) with upper part and
derivative of α-tetralone with lower part had been synthesized The efficiency of photoisomerization
were increasing in several solvent because higher steric hindrance in fjord region The
photoisomerization behavior was examined by CD and HPLC in several organic solvent The
switching selectivity (PMrsquo 0100 +100 de) was completed in n-hexane upon irradiation at 254
nm 280 nm and 310 nm The nematic liquid crystal can be inducing to chiral nematic liquid crystal
by doping the helicene
O O
hv
O O
( 10 R 11 R P)1 R = H2 R = C7H15
( 10 R 11 R M)
fjord region
R R
E7 1(2 wt)+E7 2(2 wt)+E7 References 1 Chen C-T Chou Y-C J Am Chem Soc 2000 122 7662
40
P-10
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
NG1
G2 S CNHOOC
G1 = Ph G2 = CH3G1 = Ph G2 = PhG1 = Ph G2 = 1-NpG1 = G2 = 2 -(99-dimethyl)fluorenylG1 = G2 = Iminostillbenyl
WSC-1~5
Doubly Ortho-linked cis-stillbeneFluorene Hybrids as Bipolar Organic Sensitizers Materials for Solar Cell Applications
Wei-Shan Chaodagger Wei-Kai HuangDagger Kuan-Fu ChendaggerDagger Ying-Chan HsudaggerDagger Chien-Tien Chendagger Eric
Wei-Guang DiauDagger Shin-Sheng SundaggerDagger e-mail chefv043ntnuedutw
Department of Chemistry National Taiwan Normal University Taipei Taiwandagger Department of Applied Chemistry National Chiao Tung University Hsinchu TaiwanDagger Institute of Chemistry
Academia Sinica Nankang Taipei TaiwandaggerDagger ROC
The hybrids bearing a central dibenzosuberene (DBE) unit with spiro-fluorene junction at C5 and functional C3 and C7 functional donor and acceptor groups at C3 and C7 positions respectively are the resultant 11 hybrid in the central unit and spiro-fluorene junction serve as new organic sensitizers materials for solar cell applications The donor-acceptor bipolar DBEspiro-fluorene type assembly led to absorbed increasable increases in visible-light absorption region and the spiro-fluorene prevented liquid state electrolytes (like ie I3
-I-) from permeating into the dyeTiO2 surfacepermeating destroys the dyeTiO2 surface and undesired direct also prevented the π-π transition in TiO2 level For the solar cell devices made of WSC dyes show The a conversion efficiency (η) of WSC dyes achieved of up to 510 (Voc = 766 mV Jsc = 92 mA cm-2 FF = 072 and at a dye loading = 2175 nmol cm-2) at AM 15G conditions (100 mW cm-2) (with a conversion efficiency of 783 for N719 under the same device configuration)The incident photon-to-current electron conversion efficiency (IPCE) of the solar cells based on WSC dyes all exceeds 80 from in the range of 450 to 590 nm absorption
References [1] (a) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (b) Chen C-T Majima T et al 2009 J Am Chem Soc 131 6698
400 500 600 700 8000
10
20
30
40
50
60
70
80
IPC
E (
)
Wavelength (nm)
N719 WSC-1 WSC-4 WSC-2 WSC-3 WSC-5
00 01 02 03 04 05 06 07 08 090
2
4
6
8
10
12
14
Cur
rent
Den
sity
(mAc
m-2)
Voltage(V)
N719 WSC-1 WSC-4 WSC-5 WSC-3 WSC-2
41
P-11
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Conceptually New Molecular Design Based on DonorAcceptor Hybrid as Dipolar Electroluminescent Materials for Optoelectronic Applications
Yi Wei and Chien-Tien Chen
Department of Chemistry National Taiwan Normal University Taipei Taiwan
E-mail chefv043ntnuedutw
The title molecules were examined as dipolar fluorescent materials in OLEDs Their electroluminescent efficiencies exhibit 24-48 times of improvement in HT-type than respective ET-type devices Consequently dipolar material with efficient charge transport that plays an important role for simple device fabrication would be achieved by modifying the HTET conformations of these hybrid systems
BN
C18
C9
C16C15
C17C14
C8
C7
C10
C13
C48
C11B1
C1
C5
C47
C6
C19
C49
C20
C24
C21
C12
C31
C32
C2
C4
C22
C46
C23
C50
C25
C53
C44C45
C43
C27
N1
C26
C28C42
C30
C51
C54
C29
C33
C52C3
C35
C34
C55 C57
C41
C56 C36
C40
C37
C39
C38
N
NN
C30
C31
C29
C32
C20C26C25
C28
C21C19
C33
C24C22
C40C45
C23
C41
C27
C16
C44
C42
N3
C43
C57
C46
C15
C34
C58
C52
C17
C56
N2
C51
C53
C39
C55 C35C54
C47C14
C18C11
C12
C13
C50
C38
C36
C48 C10C7N1
C49
C37
C1C9
C8
C6
C2
C5
C3
C4
N
CN
CN
N1
C1
C2
N2
C3
C40
C4
C41
C5
C10
C39
C6
C9
C42
C7
C8
C16
C38
C11
C15
C49
C43
C33
C48
C12
C14
N3
C32
C36
C35
C13
C17
C37
C44C34
C19
C18
C20
C28
C21
C47
C31
C45C46C29
C30
C22
C27
C23
C26
C24
C25
References (1) (a) Chen C-T Lin J-S Moturu M V R K Lin Y-W Wei Y Tao Y-T Chien C-H
Chem Commun 2005 3980 (b) Chen C-T Wei Y Lin J-S Moturu MV R K Chao W-S Tao Y-T Chien C-H J Am Chem Soc 2006 128 10992 (2) Wei Y Chen C-T J Am Chem Soc 2007 129 7478 (3) Wei Y Samori S Tojo S Fujitsuka M Lin J-S Chen C-T Majima T J Am Chem Soc
2009 131 6698
42
P-12
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
High efficiency and low operation voltage green PhOLED employs a pure hydrocarbon host material
Hao-Chih Chiu1 Wen-Yi Hung1 Liang-Chen Chi2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a unique molecular design strategy of an amorphous host material (SInF3) with a coplanar pure hydrocarbon p-terphenylene (indenofluorene) backbone exhibiting high triplet energy excellent thermal stability and high hole mobility for green PhOLEDs To the best of our knowledge indenofluorene derivative was reported for the first time as an efficient host material for PhOLEDs The device incorporated with SInF3 as the host which accommodated ppy2Ir(acac) as a green emitter achieved an external quantum efficiency (ηext) of 158 (60 cdA) and a power efficiency (ηp) of 63 lmW at the practical brightness of 50 cdm2 at 3 V Furthermore the device gave a brightness of 10000 cdm2 with extremely low-operating voltage at 5 V and the efficiency remains 14 (535 cdA) and 336 lmW which are the highest values ever reported for green PhOLEDs without p-i-n junction A limited external quantum efficiency roll-off was observed even at high luminance of 10000 cdm2 We attributed the excellent performances of this device to the balanced injection of both electrons and holes and the efficient confinement of triplet excitons generated within the emitting layer
SInF3 References L-C Chi W-Y Hung H-C Chiu and K-T Wong Chemical Communications Vol 2009 No 26 3892-3894 (2009)
300 400 500 600 70000
02
04
06
08
10530
492
312
347 352SInF3
absorption fluorescence phosphorescence
Inte
nsity
(au
)
Wavelength (nm)
368
330
101 102 103 104 1050
3
6
9
12
15
18
010203040506070
Qua
ntum
Effi
cien
cy (
)
Luminance (cdm2)
Power Efficiency (lm
W)
(b)
0 2 4 6 8 1010-3
10-1
101
103
105
10-6
10-4
10-2
100
102
104
Lum
inan
ce (c
dm
2 )
Voltage(V)
Current D
ensity (mA
cm2)
(a)
400 500 600 700 800
EL In
tens
ity (a
u)
Wavelength (nm)
43
P-13
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Highly Efficient Green PhOLEDs with ET-type Host Material
Zhen-Han Tsai1 Wen-Yi Hung1 Hsiao-Fan Chen2 Ken-Tsung Wong2 1Institute of Optoelectronic Sciences NTOU Keelung Taiwan 202
2Department of Chemistry NTU Taipei Taiwan 106
E-mail wenhungmailntouedutw
In this communication we report a novel starshaped molecule 246-tri(biphenyl-3-yl)- 135-triazine (T2T) and the results of using as a host in green PHOLEDs T2T is composed of an electron-transporting 135-triazine core and three biphenyl substitutes that possesses good electron mobility above 10-4 cm2 V-1s-1 at high field The twist structure between the 135-triazine unit and the terminal phenyl ring results in the reduction of the π conjugation which has high ET of 28 eV and is a potential host for green phosphors We employed a configuration ITO PEDOTPSS (30 nm) α-NPD (20 nm) TCTA (5 nm) T2T ppy2Iracac 10 wt (25 nm) ETL (50 nm) LiF (05 nm) Al to study I-V-L characteristics and EL efficiency of the devices with different ETLs Both I-V and L-V curves show a steep increase in the device indicating that the presence of TPBI or TAZ layer did block holes and improved the electron injectiontransport properties Obviously the device performance was improved by a factor of 80 with respect to the devices using original T2T as ETL The best performance was achieved by device using TPBI as ETL with a maximum luminance ηext and ηp of 109000 cd m-2175 and 59 lm W-1 respectively At a brightness of 1000 cd m-2 the device efficiency still remained in a high value (16 at 56V) We attribute the improved performance to the more-balanced charge flux and better exciton confinement within the emission layer resulted from the presence of TPBI as ETL and the exciton blocker in the multilayer device References H-F Chen S-J Yang Z-H Tsai W-Y Hung T-C Wang K-T Wong Journal of Materials Chemistry Vol 19 Issue 43 8112-8118 (2009)
N
N
N
300 400 500 60000
02
04
06
08
10
00
02
04
06
08
10
Emission (a u)
Abs
(a
u)
Wavelength (nm)
Film Solution Phos
ET
10-1 100 101 102 103 104 105 1060
3
6
9
12
15
18
0
10
20
30
40
50
60
Qua
ntum
Effi
cien
cy (
)
Brightness (cdm2)
(b) Power Efficiency (lm
W)
0 3 6 9 12 15 1810-3
10-1
101
103
105
0
300
600
900
1200 ETL T2T TPBI TAZ
Brig
htne
ss (c
dm
2 )
Voltage(V)
(a) Current D
ensity (mA
cm2)
44
P-14
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
White-emissive tandem-type hybrid organicpolymer diodes with (033 033) chromaticity coordinates
Ming-Wei Lin Chia-hsin Yeh Yu-Hao Lee and Tzung-Fang Guo Institute of Electro-Optical Science and Engineering National Cheng Kung University Tainan
Taiwan e-mail guotfmailnckuedutw
We report the fabrication of a white-emissive stacked organicpolymer light-emitting diodes (OPLED) applying the blue-emissive OLED and a yellow-emissive phenyl-substituted poly(para-phenylene vinylene) copolymer-based PLED The PLED of the single light-emissive layer prepared by the spin-coating process simplifies the deposition of multifunctional layers in OLED The PLED presented in this study also has a wide-range EL emission which is suitable for the fabrication as the decent white-lighting source The charge generation component is composed of the organic oxideAl complex as electron generation layer and a molybdenum oxide (MoO3) thin film as the hole generation layer Such a connecting structure permits the efficient injection of opposite holes and electrons injection into two adjacent emitting units and gives tandem devices superior electrical and optical performances The electroluminescence (EL) spectra of the tandem-type devices can be tuned by varying the intensity of the emissions from both its yellow- and blue-emissive components yielding a decent white-emissive EL spectrum which covers the entire visible region from 420 to 750 nm The Commission Internationale de lrsquoEclairage chromaticity coordinates are close to (033 033) for perfect white emission and also a high color r e n d e r i n g c a p a c i t y ( C R I ~ 9 0 ) a s u s e d f o r i l l u m i n a t i o n T h e E L s p e c t r a also exhibit good color stability under various bias conditions
References [1] Guo T -F Wen T-C Huang Y-S Lin M-W Tsou C-C Chung C-T OPTICS EXPRESS 2009 17 21205
Professor Tzung-Fang Guo received his Bachelor degree in Chemistry from Soochow University
(Taiwan) in 1993 and Mater Degree in Chemistry from the National Chung Cheng University (Taiwan)
in 1995 He obtained the PhD degrees in Materials Science and Engineering from University of
California Los Angeles in 2002 He joined Institute of Electro-Optical Science and Engineering
National Cheng Kung University (Taiwan) as an Assistant Professor in 2003 and became an Associate Professor in 2006
Professor Guorsquos research is related to studies of the organic electronic materials and devices including the
45
P-15
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
organicpolymer light-emitting diodes photovoltaic cells and organic field effect transistors Recently Prof Guo is
interested in the magnetoconductance response of polymer diodes made of intrinsically non-magnetic components which
is an important subject for the novel research of organic spintronics
This work is financially supported by National Science Council (NSC) of Taiwan NSC96-2113-M-006-009-MY3 the
Asian Office of Aerospace Research and Development (AOARD-09-4055) and NCKU Landmark project
46
P-15
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Synthesis of C2-Symmetric Hexabenzotriphenylene Compounds
Yi-Hsiang Chan and Hsiu-Fu Hsu
Department of Chemistry Tamkang University Tamsui Taiwan
e-mail 697160215s97tkuedutw
The performance of organic optoelectronic devices used in xerography light-emitting diode (OLED) thin-film transistor and solar cell applications is strongly affected by the charge transport characteristics of π-conjugated materials1 Important efforts have been directed to the construction of highly symmetric polycyclic aromatic hydrocarbons (PAHs) with different shapes such as saddles or twists and to the synthesis of other structures that exhibit distortions from planarity such as the helicenes or propeller-like geometries2 Herein synthesis and photophysical properties of C2-symmetric hexabenzotriphenylene derivatives will be reported References [1] Wong K-T Liao Y-L Lin C-Y Liu Y-H Hung W-Y Chen W-J Chem Commun 2007 1831-1833 [2] Barnett L Ho D M Baldridge K K Pascal Jr R A J Am Chem Soc 1999 121 727-733
47
P-16
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
Advertisement for
Organic Electronics
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨
雙進化學有限公司 益和貿易有限公司
台北縣 235 中和市中正路 965 號 2 樓 電話02-2222-8336 傳真02-2222-6117
ACROS ORGANICS 台灣代理
專業代理進口化學試藥
銷售實驗室各類耗材及精密儀器
空運期貨迅速到貨