A benzo[1,2-b:4,5-b′]dithiophene-based copolymer with deep HOMO level for efficient polymer solar cells

Solar Energy Materials and Solar Cells

Volumn 100, Issue , 2012, Pages 239-245

  Wen, Shanpeng ^a   Dong, Qingfeng ^a   Cheng, Weidong ^a   Li, Pengfei ^a   Xu, Bin ^a   Tian, Wenjing ^a  

^a Jilin University   (China)

Author keywords

Conjugated polymer; Photovoltaic devices; Polymerization

Indexed keywords

ABSORPTION BAND; ACTIVE LAYER; BULK HETEROJUNCTION; CYCLIC VOLTAMMETRIC MEASUREMENTS; DECOMPOSITION TEMPERATURE; DONOR UNITS; GOOD STABILITY; HOMO ENERGY LEVELS; OPEN CIRCUIT POTENTIAL; PHOTOVOLTAIC DEVICES; POLYMER SOLAR CELLS; POWER CONVERSION EFFICIENCIES; STILLE CROSS-COUPLING;

CONJUGATED POLYMERS; CONVERSION EFFICIENCY; HETEROJUNCTIONS; PHOTOVOLTAIC CELLS; PHOTOVOLTAIC EFFECTS; POLYMERIZATION;

COPOLYMERS;

EID: 84857794057     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2012.01.025     Document Type: Article

References (46)

1. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, and A.J. Heeger Polymer photovoltaic cell: enhanced efficiencies via a network of internal donoracceptor heterojunctions Science 270 1995 1789 1791 (Pubitemid 126635480)
2. E. Bungaard, and F.C. Krebs Low band gap polymers for organic photovoltaics Solar Energy Materials and Solar Cells 91 2007 954 985 (Pubitemid 46635041)
3. F.C. Krebs, T. Tromholt, and M. Jørgensen Upscaling of polymer solar cell fabrication using roll-to-roll processing Nanoscale 2 2010 873 886
4. M.O. Reese, S.A. Gevorgyan, M. Jørgensen, E. Bundgaard, S.R. Kurtz, D.S. Ginley, D.C. Olson, M.T. Lloyd, P. Morvillo, E.A. Katz, A. Elschner, O. Haillant, T.R. Currier, V. Shrotriya, M. Hermenau, M. Riede, K.R. Kirov, G. Trimmel, T. Rath, O. Inganäs, F. Zhang, M. Andersson, K. Tvingstedt, M.L. Cantu, D. Laird, C. McGuiness, S. Gowrisanker, M. Pannone, M. Xiao, J. Hauch, R. Steim, D.M. DeLongchamp, R. Rösch, H. Hoppe, N. Espinosa, A. Urbina, G.Y. Uzunoglu, J.B. Bonekamp, A.J.J.M.V. Breemen, C. Girotto, E. Voroshazi, and F.C. Krebs Consensus stability testing protocols for organic photovoltaic materials and devices Solar Energy Materials and Solar Cells 95 2011 1253 1267
5. Y. Kim, K. Lee, N.E. Coates, D. Moses, T.-Q. Nguyen, M. Dante, and A.J. Heeger Efficient tandem polymer solar cells fabricated by all-solution processing Science 317 2007 222 225 (Pubitemid 47076192)
6. J. Brabec, N.S. Sariciftci, and J.C. Hummelen Plastic solar cells Advanced Functional Materials 11 2001 15 26 (Pubitemid 33046405)
7. F.C. Krebs, J. Fyenbo, and M. Jorgensen Product integration of compact roll-to-roll processed polymer solar cell modules: methods and manufacture using flexographic printing, slot-die coating and rotary screen printing Journal of Materials Chemistry 20 2010 8994 9001
8. G. Yu, and A.J. Heeger Charge separation and photovoltaic conversion in polymer composites with internal donor/acceptor heterojunctions Journal of Applied Physics 78 1995 4510 4515
9. J.J.M. Halls, C.A. Walsh, N.C. Greenham, E.A. Marseglia, R.H. Friend, S.C. Moratti, and A.B. Holmes Efficient photodiodes from interpenetrating polymer networks Nature 376 1995 498 500
10. R. Qin, W. Li, C. Li, C. Du, C. Veit, H.-F. Schleiermacher, M. Andersson, Z. Bo, Z. Liu, O. Inganäs, U. Wuerfel, and F. Zhang A planar copolymer for high efficiency polymer solar cells Journal of the American Chemical Society 131 2009 14612 14613
11. F. Huang, K.-S. Chen, H.-L. Yin, S. Hau, O. Acton, Y. Zhang, J.D. Luo, and A.K.-Y. Jen Development of new conjugated polymers with donor-π-bridge- acceptor side chains for high performance solar cells Journal of the American Chemical Society 131 2009 13886 13887
12. X. Zhang, J.W. Shim, S.P. Tiwari, Q. Zhang, J.E. Norton, P.-T. Wu, S. Barlow, S.A. Jenekhe, B. Kippelen, J.-L. Brédas, and S.R. Marder Dithienopyrrolequinoxaline/pyridopyrazine donoracceptor polymers: synthesis and electrochemical, optical, charge-transport, and photovoltaic properties Journal of Materials Chemistry 21 2011 4971 4982
13. W. Ma, C. Yang, and A.J. Heeger Thermally stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology Advanced Functional Materials 15 2005 1617 1622 (Pubitemid 41454589)
14. G. Li, V. Shrotriya, Y. Yao, J. Huang, and Y. Yang Manipulating regioregular poly(3-hexylthiophene): [6,6]-phenyl-C61-butyric acid methyl ester blends - route towards high efficiency polymer solar cells Journal of Materials Chemistry 17 2007 3126 3140 (Pubitemid 47170837)
15. G. Li, V. Shrotriya, J.S. Huang, Y. Yao, T. Moriarty, K. Emery, and Y. Yang High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends Nature Materials 4 2005 864 868
16. S. Ko, R. Mondal, C. Risko, J.K. Lee, S. Hong, M.D. McGehee, J.-L. Bredas, and Z.N. Bao Tuning the optoelectronic properties of vinylene-linked donoracceptor copolymers for organic photovoltaics Macromolecules 43 2010 6685 6698
17. Z. Li, J.F. Ding, N.H. Song, J.P. Lu, and Y. Tao Development of a new s-tetrazine-based copolymer for efficient solar cells Journal of the American Chemical Society 132 2010 13160 13161
18. M.C. Scharher, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A.J. Heeger, and C.J. Brabec Design rules for donors in bulk-heterojunction solar cells - towards 10% energy-conversion efficiency Advanced Materials 18 2006 789 794
19. S.P. Wen, J.N. Pei, Y.H. Zhou, L.L. Xue, B. Xu, Y.W. Li, and W.J. Tian Synthesis and photovoltaic properties of poly(pphenylenevinylene) derivatives containing oxadiazole Journal of Polymer Science Part A: Polymer Chemistry 47 2009 1003 1012
20. J.H. Hou, M.-H. Park, S.Q. Zhang, Y. Yao, L.-M. Chen, J.-H. Li, and Y. Yang Bandgap and molecular energy level control of conjugated polymer photovoltaic materials based on benzo[1,2-b:4,5-b′]dithiophene Macromolecules 41 2008 6012 6018
21. L.J. Huo, J.H. Hou, S.Q. Zhang, H.-Y. Chen, and Y. Yang A polybenzo[1,2-b:4,5-b′]dithiophene derivative with deep HOMO level and its application in high-performance polymer solar cells Angewandte Chemie International Edition 49 2010 1500 1503
22. H.X. Zhou, L.Q. Yang, A.C. Stuart, S.C. Price, S.B. Liu, and W. You Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7% efficiency Angewandte Chemie International Edition 123 2011 3051 3054
23. S.C. Price, A.C. Stuart, and W. You Low band gap polymers based on benzo[1,2-b:4,5-b′]dithiophene: rational design of polymers leads to high photovoltaic performance Macromolecules 43 2010 4609 4612
24. Y.Y. Liang, Y. Wu, D.Q. Feng, S.T. Tsai, H.J. Son, G. Li, and L.P. Yu Development of new semiconducting polymers for high performance solar cells Journal of the American Chemical Society 131 2009 56 57
25. Y.Y. Liang, D.Q. Feng, Y. Wu, S.-T. Tsai, G. Li, C. Ray, and L.P. Yu Highly efficient solar cell polymers developed via fine-tuning of structural and electronic properties Journal of the American Chemical Society 131 2009 7792 7799
26. J.H. Hou, H.-Y. Chen, S.Q. Zhang, R.I. Chen, Y. Yang, Y. Wu, and G. Li Synthesis of a low band gap polymer and its application in highly efficient polymer solar cells Journal of the American Chemical Society 131 2009 15586 15587
27. H.-Y. Chen, J.H. Hou, S.Q. Zhang, Y.Y. Liang, G.W. Yang, Y. Yang, L.P. Yu, Y. Wu, and G. Li Polymer solar cells with enhanced open-circuit voltage and efficiency Nature Photonics 3 2009 649 653
28. L.J. Huo, J.H. Hou, H.-Y. Chen, S.Q. Zhang, Y. Jiang, T.L. Chen, and Y. Yang Bandgap and molecular level control of the low-bandgap polymers based on 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4c]pyrrole-1,4-dione toward highly efficient polymer solar cells Macromolecules 42 2009 6564 6571
29. Y.P. Zou, A. Najari, P. Berrouard, S. Beaupre, B.R. Aïch, Y. Tao, and M. Leclerc A thieno[3,4-c]pyrrole-4,6-dione-based copolymer for efficient solar cells Journal of the American Chemical Society 132 2010 5330 5331
30. C. Piliego, T.W. Holcombe, J.D. Douglas, C.H. Woo, P.M. Beaujuge, and J.M.J. Fréchet Synthetic control of structural order in N-alkylthieno[3,4-c]pyrrole-4,6-dione-based polymers for efficient solar cells Journal of the American Chemical Society 132 2010 7595 7597
31. Y. Zhang, S.K. Hau, H.-L. Yip, Y. Sun, O. Acton, and A.K.-Y. Jen Efficient polymer solar cells based on the copolymers of benzodithiophene and thienopyrroledione Chemistry of Materials 22 2010 2696 2698
32. M.J. Zhang, H.J. Fan, X. Guo, Y.H. He, Z.-G. Zhang, J. Min, J. Zhang, G.J. Zhao, X.W. Zhan, and Y.F. Li Synthesis and photovoltaic properties of a copolymer of benzo[1,2-b:4,5-b′]dithiophene and bithiazole Macromolecules 43 2010 8714 8717
33. L.J. Huo, X. Guo, S.Q. Zhang, Y.F. Li, and J.H. Hou PBDTTTZ: a broad band gap conjugated polymer with high photovoltaic performance in polymer solar cells Macromolecules 44 2011 4035 4037
34. H. Pan, Y. Li, Y. Wu, P. Liu, B.S. Ong, S. Zhu, and G. Xu Low-temperature, solution-processed, high-mobility polymer semiconductors for thin-film transistors Journal of the American Chemical Society 129 2007 4112 4113 (Pubitemid 46595405)
35. H. Pan, Y. Wu, Y. Li, P. Liu, B.S. Ong, S. Zhu, and G. Xu Benzodithiophene copolymer - a low-temperature, solution-processed high-performance semiconductor for thin-film transistors Advanced Functional Materials 17 2007 3574 3579 (Pubitemid 350221711)
36. H. Pan, Y. Li, Y. Wu, P. Liu, B.S. Ong, S. Zhu, and G. Xu Synthesis and thin-film transistor performance of poly(4,8-didodecylbenzo[1,2-b:4,5-b] dithiophene) Chemistry of Materials 18 2006 3237 3241 (Pubitemid 44147039)
37. H.J. Son, W. Wang, T. Xu, Y.Y. Liang, Y. Wu, G. Li, and L.P. Yu Synthesis of fluorinated polythienothiophene-co-benzodithiophenes and effect of fluorination on the photovoltaic properties Journal of the American Chemical Society 133 2011 1885 1894
38. Y. Liang, Z. Xu, J. Xia, S.-T. Tsai, Y. Wu, G. Li, C. Ray, and L. Yu For the bright future - bulk heterojunction polymer solar cells with power conversion efficiency of 7.4% Advanced Materials 22 2010 E135 E138
39. Z. Li, J.F. Ding, N.H. Song, X.M. Du, J.Y. Zhou, J.P. Lu, and Y. Tao Alternating copolymers of dithienyl-s-tetrazine and cyclopentadithiophene for organic photovoltaic applications Chemistry of Materials 23 2011 1977 1984
40. S.P. Wen, J.N. Pei, P.F. Li, Y.H. Zhou, W.D. Cheng, Q.F. Dong, Z.F. Li, and W.J. Tian Synthesis and photovoltaic properties of low-bandgap 4,7-dithien-2-yl-2,1,3-benzothiadiazole-based poly(heteroarylenevinylene)s Journal of Polymer Science Part A: Polymer Chemistry 49 2011 2715 2724
41. I.H. Jung, Y.K. Jung, J. Lee, J.-H. Park, H.Y. Woo, J.-I. Lee, H.Y. Chu, and H.-K. Shim Synthesis and electroluminescent properties of fluorene-based copolymers containing electron-withdrawing thiazole derivatives Journal of Polymer Science Part A: Polymer Chemistry 46 2008 7148 7161
42. Y. Zhu, R.D. Champion, and S.A. Jenekhe Conjugated donor-acceptor copolymer semiconductors with large intramolecular charge transfer: synthesis, optical properties, electrochemistry, and field effect carrier mobility of thienopyrazine-based copolymers Macromolecules 43 2010 8712 8719 (Pubitemid 46079635)
43. T. Yamamoto, D. Komarudin, M. Arai, B.L. Lee, H. Suganuma, N. Asakawa, Y. Inoue, K. Kubota, S. Sasaki, T. Fukuda, and H. Matsuda Extensive studies on π-stacking of poly(3-alkylthiophene-2,5-diyl)s and poly(4-alkylthiazole-2,5- diyl)s by optical spectroscopy, NMR analysis, light scattering analysis, and X-ray crystallography Journal of the American Chemical Society 120 1998 2047 2058 (Pubitemid 28179176)
44. Q. Peng, K. Park, T. Lin, M. Durstock, and L.M. Dai Donor-π-acceptor conjugated copolymers for photovoltaic applications: tuning the open-circuit voltage by adjusting the donor/acceptor ratio Journal of Physical Chemistry B 112 2008 2801 2808
45. S.P. Wen, J.N. Pei, Y.H. Zhou, P.F. Li, L.L. Xue, Y.W. Li, B. Xu, and W.J. Tian Synthesis of 4,7-diphenyl-2,1,3-benzothiadiazole-based copolymers and their photovoltaic applications Macromolecules 42 2009 4977 4984
46. Z.-J. Li, W.-W. Yang, and X. Gao A room-temperature fluorescence study of organofullerenes: cis-1 bisadduct with unusual blue-shifted emissions Journal of Physical Chemistry A 115 2011 6432 6437