Conjugated polymers containing electron-deficient main chains and electron-rich pendant groups: Synthesis and application to electroluminescence

Organic Electronics

Volumn 12, Issue 6, 2011, Pages 1048-1062

  Wang, Kun Li ^a   Leung, Man Kit ^b   Hsieh, Li Ga ^a   Chang, Chin Chuan ^b   Lee, Kueir Rarn ^c   Wu, Chun Lung ^d   Jiang, Jyh Chiang ^e   Tseng, Chieh Yu ^e   Wang, Hui Tang ^e  

^a NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c CHUNG YUAN CHRISTIAN UNIVERSITY   (Taiwan)

^d TAIWAN TEXTILE RESEARCH INSTITUTE   (Taiwan)

^e NATIONAL TAIWAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

Author keywords

Bipolar; Conjugated polymer; Donor acceptor; Fluorene; PLED

Indexed keywords

CHAINS; ELECTROLUMINESCENCE; ELECTRONS; ENERGY TRANSFER; GLASS TRANSITION; POLYDISPERSITY; THERMODYNAMIC STABILITY;

2 ,1 ,3-BENZOTHIADIAZOLE; BIPOLAR; DONOR ACCEPTORS; ELECTROLUMINESCENCE EFFICIENCIES; FLUORENES; INTERMOLECULAR ENERGY TRANSFER; NUMBER AVERAGE MOLECULAR WEIGHT; PLED;

CONJUGATED POLYMERS;

EID: 79953878441     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2011.03.020     Document Type: Article

References (43)

1. G. Zhang, W. Li, B. Chu, Z. Su, D. Yang, F. Yan, Y. Chen, D. Zhang, L. Han, J. Wang, H. Liu, G. Che, Z. Zhang, and Z. Hu Highly efficient photovoltaic diode based organic ultraviolet photodetector and the strong electroluminescence resulting from pure exciplex emission Org. Electron. 10 2009 352 356
2. B. Ma, B.J. Kim, L. Deng, D.A. Poulsen, M.E. Thompson, and J.M.J. Fréchet Bipolar copolymers as host for electroluminescent devices: effects of molecular structure on film morphology and device performance Macromolecules 40 2007 8156 8161 (Pubitemid 350150527)
3. S.H. Chen, and Y. Chen Poly(p-phenylenevinylene) derivatives containing electron-transporting aromatic triazole or oxadiazole segments Macromolecules 38 2005 53 60 (Pubitemid 40135795)
4. S.T. Huang, D.J. Liaw, L.G. Hsieh, C.C. Chang, M.K. Leung, K.L. Wang, W.T. Chen, K.R. Lee, J.Y. Lai, L.H. Chan, and C.T. Chen Synthesis and electroluminescent properties of polyfluorene-based conjugated polymers containing bipolar groups J. Polym. Sci. A Polym. Chem. 47 2009 6231 6245
5. C.C. Chi, C.L. Chiang, S.W. Liu, H. Yueh, and C.T. Chen Achieving high-efficiency non-doped blue organic light-emitting diodes: charge-balance control of bipolar blue fluorescent materials with reduced hole-mobility J. Mater. Chem. 19 2009 5561 5571
6. H. Wu, J. Zou, F. Liu, L. Wang, A. Mikhailovsky, G.C. Bazan, W. Yang, and Y. Cao Efficient single active layer electrophosphorescent white polymer light-emitting diodes Adv. Mater. 20 2008 696 702
7. M.H. Kim, M.J. Cho, K.H. Kim, M.H. Hoang, T.W. Lee, J.I. Jin, N.S. Kang, J.W. Yu, and D.H. Choi Organic donor-σ-acceptor molecules based on 1,2,4,5-tetrakis((E)-2-(5′-hexyl-2,2′-bithiophen-5-yl)vinyl)benzene and perylene diimide derivative and their application to photovoltaic devices Org. Electron. 10 2009 1429 1441
8. S. Karak, V.S. Reddy, S.K. Ray, and A. Dhar Organic photovoltaic devices based on pentacene/N,N′-dioctyl-3,4,9,10-perylenedicarboximide heterojunctions Org. Electron. 10 2009 1006 1010
9. J.D. Myers, T.K. Tseng, and J. Xue Photocarrier behavior in organic heterojunction photovoltaic cells Org. Electron. 10 2009 1182 1186
10. E. Zhou, S. Yamakawa, K. Tajima, C. Yang, and K. Hashimoto Synthesis and photovoltaic properties of diketopyrrolopyrrole-based donor-acceptor copolymers Chem. Mater. 21 2009 4055 4061
11. S. Celebi, A. Balan, B. Epik, D. Baran, and L. Toppare Donor acceptor type neutral state green polymer bearing pyrrole as the donor unit Org. Electron. 10 2009 631 636
12. M. Ili, M. Pamuk, F. Algi, A.M. Önal, and A. Cihaner A new soluble neutral state black electrochromic copolymer via a donor-acceptor approach Org. Electron. 11 2010 1255 1260
13. A. Benor, A. Hoppe, V. Wagner, and D. Knipp Electrical stability of pentacene thin film transistors Org. Electron. 8 2007 749 758 (Pubitemid 47600719)
14. D.H. Kim, B.L. Lee, H. Moon, H.M. Kang, E.J. Jeong, J.I. Park, K.M. Han, S. Lee, B.W. Yoo, B.W. Koo, J.Y. Kim, W.H. Lee, K. Cho, H.A. Becerril, and Z. Bao Liquid-crystalline semiconducting copolymers with intramolecular donor-acceptor building blocks for high-stability polymer transistors J. Am. Chem. Soc. 131 2009 6124 6132
15. W. Wu, Y. Liu, Y. Wang, H. Xi, X. Gao, C. Di, G. Yu, W. Xu, and D. Zhu High-performance, low-operating-voltage organic field-effect transistors with low pinch-off voltages Adv. Funct. Mater. 18 2008 810 815 (Pubitemid 351430223)
16. K.L. Wang, Y.L. Liu, J.W. Lee, K.G. Neoh, and E.T. Kang Nonvolatile electrical switching and write-once read-many-times memory effects in functional polyimides containing triphenylamine and 1,3,4-oxadiazole moieties Macromolecules 43 2010 7159 7164
17. G. Liu, Q.D. Ling, E.T. Kang, K.G. Neoh, D.J. Liaw, F.C. Chang, C.X. Zhu, and D.S.H. Chan Bistable electrical switching and write-once read-many-times memory effect in a donor-acceptor containing polyfluorene derivative and its carbon nanotube composites J. Appl. Phys. 102 2007 Art No. 024502
18. Y.L. Liu, K.L. Wang, G.S. Huang, C.X. Zhu, E.S. Tok, K.G. Neoh, and E.T. Kang Volatile electrical switching and static random access memory effect in a functional polyimide containing oxadiazole moieties Chem. Mater. 21 2009 3391 3399
19. Y.L. Liu, Q.D. Ling, E.T. Kang, K.G. Neoh, D.J. Liaw, K.L. Wang, W.T. Liou, C.X. Zhu, and D.S.H. Chan Volatile electrical switching in a functional polyimide containing electron-donor and -acceptor moieties J. Appl. Phys. 105 2009 Art No. 044501
20. K.L. Wang, T.Y. Tseng, H.L. Tsai, and S.C. Wu Resistive switching polymer materials based on poly(aryl ether)s containing triphenylamine and 1,2,4-triazole moieties J. Polym. Sci. A Polym. Chem. 46 2008 6861 6871
21. K.L. Wang, Y.L. Liu, I.H. Shih, K.G. Neoh, and E.T. Kang Synthesis of polyimides containing triphenylamine-substituted triazole moieties for polymer memory applications J. Polym. Sci. A Polym. Chem. 48 2010 5790 5800
22. Q.D. Ling, D.J. Liaw, E.Y.H. Teo, C. Zhu, D.S.H. Chan, E.T. Kang, and K.G. Neoh Polymer memories: bistable electrical switching and device performance Polymer 48 2007 5182 5201 (Pubitemid 47247452)
23. M. Pamuk, S. Tirke, A. Cihaner, and F. Algi A new low-voltage-driven polymeric electrochromic Polymer 51 2010 62 68
24. S. Tarkuc, Y.A. Udum, and L. Toppare Tuning of the neutral state color of the π-conjugated donor-acceptor-donor type polymer from blue to green via changing the donor strength on the polymer Polymer 50 2009 3458 3464
25. P. Karastatiris, J.A. Mikroyannidis, and I.K. Spiliopoulos Bipolar poly(p-phenylene vinylene)s bearing electron-donating triphenylamine or carbazole and electron-accepting quinoxaline moieties J. Polym. Sci. A Polym. Chem. 46 2008 2367 2378 (Pubitemid 351430159)
26. S. Xun, Q. Zhou, H. Li, D. Ma, L. Wang, X. Jing, and F. Wang Synthesis, characterization, and electroluminescence of PPV copolymers containing electron and hole-transporting units J. Polym. Sci. A Polym. Chem. 46 2008 1566 1576 (Pubitemid 351310826)
27. C. Nagamani, C. Versek, M. Thorn, M.T. Tuominen, and S. Thayumanavan Proton conduction in 1H-1,2,3-triazole polymers: imidazole-like or pyrazole-like? J. Polym. Sci. A Polym. Chem. 48 2010 1851 1858
28. R.A. Potrekar, M.P. Kulkarni, R.A. Kulkarni, and S.P. Vernekar Polybenzimidazoles tethered with N-phenyl 1,2,4-triazole units as polymer electrolytes for fuel cells J. Polym. Sci. A Polym. Chem. 47 2009 2289 2303
29. L. Huo, Z. Tan, X. Wang, Y. Zhou, M. Han, and Y. Li Novel two-dimensional donor-acceptor conjugated polymers containing quinoxaline units: synthesis, characterization, and photovoltaic properties J. Polym. Sci. A Polym. Chem. 46 2008 4038 4049
30. L. Huo, C. He, M. Han, E. Zhou, and Y. Li Alternating copolymers of electron-rich arylamine and electron-deficient 2,1,3-benzothiadiazole: synthesis, characterization and photovoltaic properties J. Polym. Sci. A Polym. Chem. 45 2007 3861 3871 (Pubitemid 47328881)
31. K.L. Wang, S.T. Huang, L.G. Hsieh, and G.S. Huang Synthesis, optical and electrochemical properties of new hyperbranched poly(triphenylamine amide)s Polymer 49 2008 4087 4093
32. F.S. Mancilha, B.A. DaSilveira Neto, A.S. Lopes, P.F. Moreira Jr, F.H. Quina, R.S. Gonalves, and J. Dupont Are molecular 5,8-π-extended quinoxaline derivatives good chromophores for photoluminescence applications? Eur. J. Org. Chem. 2006 4924 4933
33. M. Grell, D.D.C. Bradley, M. Inbasekaran, and E.P. Woo A glass-forming conjugated main-chain liquid crystal polymer for polarized electroluminescence applications Adv. Mater. 9 1997 798 802 (Pubitemid 127532934)
34. T. Förster 10th Spiers Memorial Lecture. Transfer mechanisms of electronic excitation Discuss. Faraday Soc. 27 1959 7 17
35. F. Huang, L. Hou, H. Wu, X. Wang, H. Shen, W. Cao, W. Yang, and Y. Cao High-efficiency, environment-friendly electroluminescent polymers with stable high work function metal as a cathode: green- and yellow-emitting conjugated polyfluorene polyelectrolytes and their neutral precursors J. Am. Chem. Soc. 126 2004 9845 9853 (Pubitemid 39031066)
36. M. Yan, L.J. Rothberg, F. Papadimitrakopoulos, M.E. Galvin, and T.M. Miller Defect quenching of conjugated polymer luminescence Phys. Rev. Lett. 73 1994 744 747 (Pubitemid 24976314)
37. D. Oelkrug, A. Tompert, J. Gierschner, H.J. Egelhaaf, M. Hanack, M. Hohloch, and E. Steinhuber Tuning of fluorescence in films and nanoparticles of oligophenylenevinylenes J. Phys. Chem. B 102 1998 1902 1907 (Pubitemid 128586640)
38. Y.Y. Li, A.M. Ren, J.K. Feng, L. Yang, and C.C. Sun A theoretical investigation on the absorption and emission properties of isomeric benzofuran trimers Opt. Mater. 29 2007 1571 1578 (Pubitemid 46946978)
39. L. Yang, J.K. Feng, Y. Liao, and A.M. Ren Theoretical studies on the electronic and optical properties of two blue-emitting fluorene-pyridine-based copolymers Opt. Mater. 29 2007 642 650 (Pubitemid 46038930)
40. L. Yang, J.K. Feng, W.Y. Wong, and S.Y. Poon Electronic structure and optical properties of germanium-bridged platinum(II)-containing diethynylfluorene monomer and oligomers: a theoretical investigation Polymer 48 2007 6457 6463 (Pubitemid 47483818)
41. F. Huang, Y. Zhang, M.S. Liu, and A.K.Y. Jen Electron-rich alcohol-soluble neutral conjugated polymers as highly efficient electron-injecting materials for polymer light-emitting diodes Adv. Funct. Mater. 19 2009 2457 2466
42. J. Demas, and J. Addington Luminescence quenching of the tris (2,2′-bipyridine) ruthenium (II) and tris (1,10-phenanthroline) ruthenium (II) cations J. Am. Chem. Soc. 98 1976 5800 5806
43. R.H. Schweitzer, and G.W. Brudvig Fluorescence quenching by chlorophyll cations in photosystem II Biochemistry 36 1997 11351 11359 (Pubitemid 27408617)