Synthesis and applications of 2,7-carbazole-based conjugated main-chain copolymers containing electron deficient bithiazole units for organic solar cells

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 48, Issue 23, 2010, Pages 5479-5489

  Patra, Dhananjaya ^a   Sahu, Duryodhan ^a   Padhy, Harihara ^a   Kekuda, Dhananjay ^b   Chu, Chih Wei ^a,b   Lin, Hong Cheu ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^b RESEARCH CENTER FOR APPLIED SCIENCES   (Taiwan)

Author keywords

Bithiazole units; Bulk heterojunction; Copolymers; Donor acceptor

Indexed keywords

ABSORPTION BAND; ACTIVE LAYER; AIR STABILITY; BAND GAPS; BITHIAZOLE; BULK HETEROJUNCTION; BUTYRIC ACIDS; DONOR-ACCEPTORS; ELECTRON ACCEPTOR; ELECTRON DONORS; ELECTRON-DEFICIENT; FILL FACTOR; HIGHEST OCCUPIED MOLECULAR ORBITAL; METHYL ESTERS; ORGANIC SOLAR CELL; POWER CONVERSION EFFICIENCIES; SOLAR EMISSION; UV- AND; VISIBLE REGION; WEIGHT RATIOS; WHITE-LIGHT ILLUMINATION;

ABSORPTION; ABSORPTION SPECTROSCOPY; CONVERSION EFFICIENCY; COPOLYMERIZATION; COPOLYMERS; ELECTROCHEMICAL PROPERTIES; ELECTRON ENERGY LEVELS; ELECTRONS; EMISSION SPECTROSCOPY; ESTERIFICATION; ESTERS; FATTY ACIDS; MOLECULAR ORBITALS; OPEN CIRCUIT VOLTAGE; ORGANIC POLYMERS; PLASTIC PRODUCTS; POLYCYCLIC AROMATIC HYDROCARBONS; SOLAR CELLS;

HETEROJUNCTIONS;

EID: 78349291944     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24356     Document Type: Article

References (74)

1. (a), Roncali, J., Chem Rev 1997, 97, 173 - 205
2. (b), Yu, G.,;, Gao, J.,;, Hummelen, J. C.,;, Wudl, F.,;, Heeger, A. J., Science 1995, 270, 1789 - 1791
3. (c), Cheng, Y. J.,;, Yang, S. H.,;, Hsu, C. S., Chem Rev 2009, 109, 5868 - 5923
4. (d), Bundgaard, E.,;, Krebs, F. C., Sol Energy Mater Sol Cells 2007, 91, 954 - 985
5. (e), Shrotriya, V., Nat Photonics 2009, 3, 447 - 449.
6. (a), Velusami, M.,;, Huang, J.-H.,;, Hsu, Y.-C.,;, Chou, H.-H,;, Ho, K.-C.,;, Wu, P.-L.,;, Chang, W.-H.,;, Lin, J. T.,;, Chu, C.-W., Organic Letters 2009, 4898 - 4901
7. (b), Huang, J. H.,;, Velusami, M.,;, Ho, K. C.,;, Lin, J.-T.,;, Chu, C.-W., J Mater Chem 2010, 20, 2820 - 2825
8. (c), Zhang J.,;, Yang Y.,;, He C.,;, He Y.,;, Zhao G.,;, Li Y., Macromolecules 2009, 42, 7619 - 7622
9. (d), Walker, B.,;, Tamayo, A. B.,;, Dang, X.-D.,;, Zalar, P.,;, Seo, J. H.,;, Gercia, A.,;, Tantiwiwat, M.,;, Nguyen, T.-Q., Adv Funct Mater 2009, 19, 3063 - 3069.
10. (a), Brabec, C. J.,;, Sariciftci, N. S.,;, Hummelen, J. C., Adv Funct Mater 2001, 11, 15 - 26
11. (b), Coakley, K. M.,;, McGehee, M. D., Chem Mater 2004, 16, 4533 - 4542
12. (c), G, Li.,;, V, Shrotriya.,;, Huang, J.,;, Yao, Y.,;, Moriarty, T.,;, Emery, K.,;, Yang, Y., Nat Mater 2005, 4, 864 - 868
13. (d), Gunes, S.,;, Neugebauer, H.,;, Sariciftci, N. S., Chem Rev 2007, 107, 1324 - 1338
14. (e), Thompson, B. C.,;, Frechet, J. M. J., Angew Chem Int Ed 2008, 47, 58 - 77.
15. (a), Liang, Y.,;, Feng, D.,;, Wu, Y.,;, Tsai, S.-T.,;, Li, G.,;, Ray, C.,;, Yu, L., J Am Chem Soc 2009, 131, 7792 - 7799
16. (b), Chen, H.-Y.,;, Hou, J.,;, Zhang, S.,;, Liang, Y.,;, Yang, G.,;, Yang, Y.,;, Yu, L.,;, Wu, Y.,;, Li. G., Nat Photonics 2009, 3, 649 - 653
17. (c), Park, S. H.,;, Roy, A.,;, Beaupré, S.,;, Cho, S.,;, Coates, N.,;, Moon, J. S.,;, Moses, D.,;, Leclerc, M.,;, Lee, K.,;, Heeger, A. J., Nat Photonics 2009, 3, 297 - 303.
18. (a), Zho, Y.,;, Gendron, D.,;, Neagu-Plesu, R.,;, Leclerc, M., Macromolecules 2009, 42, 6361 - 6365
19. (b), Li, Y.,;, Zhu, Y., Adv Mater 2008, 20, 2952 - 2958.
20. (a), Huo, L.,;, Tan, Z. A.,;, Wang, X.,;, Zhou, Y.,;, Han, M.,;, Li, Y., J Polym Sci Part A: Polym Chem 2008, 46, 4038 - 4049
21. (b), Chen, C.-P.,;, Chan, S.-H.,;, Chao, T.-C.,;, Ting, C.,;, Ko, B.-T., J Am Chem Soc 2008, 130, 12828 - 12833.
22. Dennler, G.,;, Scharber, M.,;, Brabec, C. J., Adv Mater 2009, 21, 1323 - 1338.
23. Brédas, J.-L.,;, Beljonne, D.,;, Coropceanu, V.,;, Cornil, J., Chem. Rev. 2004, 104, 4971 - 5003.
24. (a), Petersen, M. H.,;, Hagemann, O.,;, Nielsen, K.T.,;, Jorgensen, M.,;, Krebs, F.C., Sol Energy Mater Sol Cells, 2007, 91, 996 - 1009
25. (b), Peng, Q.,;, Xu, J.,;, Zheng,. J Polym Sci Part A: Polym Chem 2009, 47, 3399 - 3408
26. (c), Huo, L.,;, Tan, Z.,;, Wang, X.,;, Zhou, Yi.,;, Han, M.,;, Li, Y., J Polym Sci Part A: Polym Chem 2007, 46, 4038 - 4049.
27. (a), Blouin, N.,;, Michaud, A.,;, Leclerc, M., Adv Mater 2007, 19, 2295 - 2300
28. (b), Blouin, N.,;, Michaud, A.,;, Gendron, D.,;, Wakim, S.,;, Blair, E.,;, Neaguplesu, R.,;, Belletete, M.,;, Durocher, G.,;, Tao, Y.,;, Leclerc, M., J Am Chem Soc 2008, 130, 732 - 742
29. (c), Zou, Y.,;, Gendron, D.,;, Ach, R. B.,;, Najari, A.,;, Tao, Y.,;, Leclerc, M., Macromolecules 2009, 42, 2891 - 2894
30. (d), Qin, R. P.,;, Li, W. W.,;, Li, C. H.,;, Du, C.,;, Veit, C.,;, Schleiermacher, H. F.,;, Andersson, M.,;, Bo, Z. S.,;, Liu, Z. P.,;, Inganäs, O.,;, Wuerfel, U.,;, Zhang, F. L., J Am Chem Soc 2009, 131, 14612
31. (e), Zhang, M.,;, Fan, H.,;, Guo, X.,;, He, Y.,;, Zhang, Z.,;, Min, J.,;, Zhang, J.,;, Zhao, G.,;, Zhan, X.,;, Li, Y., Macromolecules 2010, 43, 5706 - 5712.
32. (a), Daun, C.,;, Cai, W.,;, Huang, F.,;, Zhang, J.,;, Wang, M.,;, Yang, T.,;, Zhong, C.,;, Gong, X.,;, Cao, Y., Macromolecules 2010, 43, 5262 - 5268
33. (b), Boudreault, P. T.,;, Michaud, A.,;, Leclerc, M., Macromol Rapid Commun 2007, 28, 2176 - 2179.
34. (a), Muhlbacher, D.,;, Scharber, M.,;, Morana, M.,;, Zhu, Z.,;, Waller, D.,;, Gaudiana, R.,;, Brabec, C., Adv Mater 2006, 18, 2884 - 2889
35. (b), Peet, J.,;, Kim, J. Y.,;, Coates, N. E.,;, Ma, W. L.,;, Moses, D.,;, Heeger, A. J.,;, Bazan, G. C., Nat Mater 2007, 6, 497 - 500
36. (c), Li, K. C.,;, Hsu, Y.-C.,;, Lin, J.-T.,;, Yang, C.-C.,;, Wei, K. W.,;, Lin, H.-C., J Polym Sci Part A: Polym Chem 2009, 47, 2073 - 2092.
37. (a), Zhou, E.,;, Nakamura, M.,;, Nishizawa, T.,;, Zhang, Y.,;, Wei, Q.,;, Tajima, K.,;, Yang, C.,;, Hashimoto, K., Macromolecules. 2008, 41, 8302 - 8305
38. (b), Zhou, E.,;, Wei. Q.,;, Yamakawa, S.,;, Zhang, Y.,;, Tajima, K.,;, Yang, C.,;, Hashimoto, K., Macromolecules 2010, 21, 821 - 826
39. (c), Yue, W.,;, Zhao, Y.,;, Shao, S.,;, Tian, H.,;, Xie, Z.,;, Geng, Y.,;, Wang, F., J Mater Chem 2009, 19, 2199 - 2206.
40. (a), Liao, L.,;, Dai, L.,;, Smith, A.,;, Durstock, M.,;, Lu, J.,;, Ding, J.,;, Tao, Y., Macromolecules 2007, 40, 9406 - 9412
41. (b), Hou, J.,;, Chen, H.-Y.,;, Zhang, S.,;, Li, G.,;, Yang, Y., J Am Chem Soc 2008, 130, 16144 - 16145
42. (c), Huo, L.,;, Chen, H.-Y.,;, Hou, J.,;, Chen. T. L.,;, Yang, Y., Chem Commun 2009, 5570 - 5572.
43. (a), Wang, E.,;, Wang, M.,;, Wang, L.,;, Duan, C.,;, Zhang, J.,;, Cai, W.,;, He, C.,;, Wu, H.,;, Cao, Y., Macromolecules 2009, 42, 4410 - 4415
44. (b), Chen, M. H.,;, Hou, J.,;, Hong, Z.,;, Yang, G.,;, Sista, S.,;, Chen, L. M.,;, Yang, Y., Adv Mater 2009, 21, 4238 - 4242
45. (c), Gadisa, A.,;, Mammo, W.,;, Andersson, L. M.,;, Admassive, S.,;, Zhang, F.,;, Andersson, M. R.,;, Inganäs, O., Adv Funct Mater 2007, 17, 3836 - 3842
46. (d), Li, Y.,;, Li, H.,;, Xu, B.,;, Li, Z.,;, Chen, F.,;, Feng, D.,;, Zhang. J.,;, Tian, W., Polymer 2010, 51, 1786 - 1795.
47. (a), Tang, W.,;, Kietzke, T.,;, Vemulamada P.,;, Chen, Z.-K., Polym Sci Part A: Polym Chem 2007, 4, 5266 - 5276
48. (b), Huang, J. H.,;, Li, K. C.,;, Wei, H. Y.,;, Chen, P. Y.,;, Lin, L.Y.,;, Kekuda, D.,;, Lin, H. C.,;, Ho, K. C.,;, Chu, C. W., Organic Electronics 2009, 10, 1109 - 1115
49. (c), Li, K.-C.,;, Hsu, Y.-C.,;, Lin, J.-T.,;, Yang, C.-C.,;, Wei, K. W.,;, Lin, H.-C., J Polym Sci Part A: Polym Chem 2008, 46, 4285 - 4304
50. (d), Huang, J. H.,;, Ho, Z. Y.,;, Kekuda, D.,;, Chang, Y.,;, Chu, C. W.,;, Ho, K. C., Nanotechnology 2009, 20, 025202.
51. (a), Osaka, I.,;, Sauvé, G.,;, Zhang, R.,;, Kowalewski, T.,;, McCullough, R. D., Adv Mater 2007, 19, 4160 - 4165
52. (b), Mamada, M.,;, Nishida, J.,;, Kumaki, D.,;, Tokito, S., Chem Mater 2007, 19, 5404 - 5409.
53. (a), Yasuda, T.,;, Sakai, Y.,;, Aramaki, S.,;, Yamamoto, T., Chem Mater 2005, 17, 6060 - 6068
54. (b), Yamamoto, T.,;, Suganuma, H.,;, Maruyama, T.,;, Inoue, T.,;, Muramatsu, Y.,;, Arai, M.,;, Komarudin, D.,;, Ooba, N.,;, Tomaru, S.,;, Sasaki, S.,;, Kubota, K., Chem Mater 1997, 9, 1217 - 1225.
55. (a), Ahmed, E.,;, Kim, F. S.,;, Xin, H.,;, Jenekhe, S. A., Macromolecules 2009, 42, 8615 - 8618
56. (b), Curtis, M. D.,;, Nanos, J. I.,;, Moon, H.,;, Jhang, W. S., J Am Chem Soc 2007, 129, 15072 - 15084.
57. (a), Wong, W.-Y.,;, Wang, X.-Z.,;, He, Z.,;, Chen, K.-K.,;, Djuri, A. B.,;, Cheung, K.-Y.,;, Yip, C.-T.,;, Ng, A. M.-C.,;, Xi, Y. Y.,;, Mak, C. S. K.,;, Chan, W.-K., J Am Chem Soc 2007, 129, 14372 - 14380
58. (b), Lee, J.,;, Jung, B. J.,;, Lee, S. K.,;, Lee, J. I.,;, Cho, H. J.,;, Shim, H. K., J Polym Sci Part A: Polym Chem 2005, 43, 1845 - 1857.
59. (a), Li, K. C.,;, Huang, J. H.,;, Hsu, Y. C.,;, Huang, P.J.,;, Chu, C. W.,;, Lin, J. T.,;, Ho, K. C., Lin, H. C., Macromolecules 2009, 42, 3681 - 3693
60. (b), Huang, J. H.,;, Li, K. C.,;, Kekuda, D.,;, Padhy, H. H.,;, Lin, H. C.,;, Ho. K. C.,;, Chu, C. W., J Mater Chem 2010, 20, 3295 - 3300.
61. Wei, Y.,;, Yang, Y.,;, Yeh, J.-M., Chem Mater 1996, 8, 2659 - 2666.
62. (a), Zhag, S.,;, Guo, Y.,;, Fan, H.,;, Liu, Y.,;, Chen, H.-Y.,;, Yang, G.,;, Zhan, X.,;, Liu, Y.,;, Li, Y.,;, Yang, Y., J Polym Sci Part A: Polym Chem 2009, 47, 5498 - 5508.
63. (a), Chan, S.-H.,;, Chen, C.-P.,;, Chao, T.-C.,;, Ting, C.,;, Lin, C.-S.,;, Ko, B.-T., Macromolecules 2008, 41, 5519 - 5526
64. (b), Jung, I. H.,;, Yu, J.,;, Jeong, E.,;, Kwon, S.,;, Kong, H.,;, Lee, K.,;, Woo, H.Y.,;, Shim, H.K., Chem Eur J 2010, 16, 3743 - 3752.
65. (a), Xaio, S.,;, Stuart, A. C.,;, Liu, S.,;, You, W., ACS Appl Mater Intrfaces 2007, 7, 1613 - 1621
66. (b), Li, Y.,;, Li, Z.,;, Wang, C.,;, Li, H.,;, Lu, H.,;, Xu, B.,;, Tian, W., Polym Sci Part A: Polym Chem 2010, 48, 2765 - 2776
67. (c), Wong, W.-Y., Macromol Chem Phys 2008, 209, 14 - 24.
68. (a), Liang, T. C.,;, Chiang, I. H.,;, Yang, P. J.,;, Kekuda, D.,;, Chu, C. W.,;, Lin, H. C., J Polym Sci Part A: Polym Chem 2009, 47, 5998 - 6013.
69. (a), Liang, Y.,;, Wu, Y.,;, Feng, D.,;, Tsai, S.-T.,;, Son, H.-J.,;, Li, G.,;, Yu, L., J Am Chem Soc 2009, 131, 56 - 57
70. (b), Jung, I. H.,;, Kim, H.,;, Park, M.-J.,;, Kim, B.,;, Park, J.-H.,;, Jeong, E.,;, Woo, H. Y.,;, Yoo, S.,;, Shim, H.-K., J Polym Sci Part A: Polym Chem 2010, 48, 1423 - 1432.
71. (a), Baek, N. S.,;, Hau, S. K.,;, Yip, H. L.,;, Acton, O.,;, Chen, K. S.,;, Jen, A. K. Y., Chem Mater 2008, 20, 5734 - 5736.
72. Zhou, Y. H.,;, Wang, Y. N.,;, Wu, W. C.,;, Wang, H.,;, Han, L.,;, Tian, W. J.,;, Bassler, H., Sol Energy Mater Sol Cells 2007, 91, 1842 - 1848
73. (b), Liu, J.,;, Shi, Y. J.,;, Yang, Y., Adv Funct Mater 2001, 11, 420 - 424.
74. Li, Y.,;, Xue, L.,;, Li, H.,;, Xu, B.,;, Wen, S.,;, Tian, W., Macromolecules 2009, 42, 4491 - 4499.