Improved Charge Transport and Absorption Coefficient in Indacenodithieno[3,2‐b]thiophene‐based Ladder‐Type Polymer Leading to Highly Efficient Polymer Solar Cells

Advanced MaterialsVolume 24, Issue 47 p. 6356-6361 Communication Improved Charge Transport and Absorption Coefficient in Indacenodithieno[3,2-b]thiophene-based Ladder-Type Polymer Leading to Highly Efficient Polymer Solar Cells Yun-Xiang Xu, Yun-Xiang Xu Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorChu-Chen Chueh, Chu-Chen Chueh Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorHin-Lap Yip, Hin-Lap Yip Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorFei-Zhi Ding, Fei-Zhi Ding Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195, USASearch for more papers by this authorYong-Xi Li, Yong-Xi Li Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorChang-Zhi Li, Chang-Zhi Li Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorXiaosong Li, Xiaosong Li Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195, USASearch for more papers by this authorWen-Chang Chen, Wen-Chang Chen Department of Chemical Engineering and Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, TaiwanSearch for more papers by this authorAlex K.-Y. Jen, Corresponding Author Alex K.-Y. Jen [email protected] Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USADepartment of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USA.Search for more papers by this author Yun-Xiang Xu, Yun-Xiang Xu Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorChu-Chen Chueh, Chu-Chen Chueh Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorHin-Lap Yip, Hin-Lap Yip Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorFei-Zhi Ding, Fei-Zhi Ding Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195, USASearch for more papers by this authorYong-Xi Li, Yong-Xi Li Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorChang-Zhi Li, Chang-Zhi Li Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USASearch for more papers by this authorXiaosong Li, Xiaosong Li Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195, USASearch for more papers by this authorWen-Chang Chen, Wen-Chang Chen Department of Chemical Engineering and Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, TaiwanSearch for more papers by this authorAlex K.-Y. Jen, Corresponding Author Alex K.-Y. Jen [email protected] Department of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USADepartment of Materials Science and Engineering, University of Washington, Seattle, WA 98195, USA.Search for more papers by this author First published: 24 September 2012 https://doi.org/10.1002/adma.201203246Citations: 335Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract A novel ladder-type donor (IDTT) is developed by substituting the two outward thiophenes of the IDT donor with two thieno[3,2-b]thiophenes. The polymer derived from this donor possesses longer effective conjugation and better planarity, which improves electron delocalization along the polymer backbone and charge mobility. The polymer solar cell device using PIDTT-DFBT shows a high power conversion efficiency of 7.03% with a large open-circuit voltage of 0.95 V without using any additives or post-solvent/thermal annealing processes. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description adma_201203246_sm_suppl.pdf612.2 KB suppl Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 Z. He, C. Zhong, X. Huang, W.-Y. Wong, H. Wu, L. Chen, S. Su, Y. Cao, Adv. Mater. 2011, 23, 4636. 2 C. E. Small, S. Chen, J. Subbiah, C. M. Amb, S.-W. Tsang, T.-H. Lai, J. R. Reynolds, F. So, Nat. Photonics 2012, 6, 115. 3 X. Li, W. C. H. Choy, L. Huo, F. Xie, W. E. I. Sha, B. Ding, X. Guo, Y. Li, J. Hou, J. You, Y. Yang, Adv. Mater. 2012, 24, 3046. 4 T. Yang, M. Wang, C. Duan, X. Hu, L. Huang, J. Peng, F. Huang, X. Gong, Energy Environ. Sci. 2012, 5, 8208. 5 Z. He, C. Zhong, S. Su, M. Xu, H. Wu, Y. Cao, Nat. Photonics 2012, 6, 593. 6 C.-Y. Yu, C.-P. Chen, S.-H. Chan, G.-W. Hwang, C. Ting, Chem. Mater. 2009, 21, 3262. 7 S.-H. Chan, C.-P. Chen, T.-C. Chao, C. Ting, C.-S. Lin, B.-T. Ko, Macromolecules 2008, 41, 5519. 8 C. P. Chen, S. H. Chan, T. C. Chao, C. Ting, B. T. Ko, J. Am. Chem. Soc. 2008, 130, 12828. 9 I. McCulloch, R. S. Ashraf, L. Biniek, H. Bronstein, C. Combe, J. E. Donaghey, D. I. James, C. B. Nielsen, B. C. Schroeder, W. Zhang, Acc. Chem. Res. 2012, 45, 714. 10 B. C. Schroeder, R. S. Ashraf, S. Thomas, A. J. P. White, L. Biniek, C. B. Nielsen, W. Zhang, Z. Huang, P. S. Tuladhar, S. E. Watkins, T. D. Anthopoulos, J. R. Durrant, I. McCulloch, Chem. Commun. 2012, 48, 7699. 11 H. Bronstein, R. S. Ashraf, Y. Kim, A. J. White, T. Anthopoulos, K. Song, D. James, W. Zhang, I. McCulloch, Macromol. Rapid Commun. 2011, 32, 1664. 12 H. Bronstein, D. S. Leem, R. Hamilton, P. Woebkenberg, S. King, W. Zhang, R. S. Ashraf, M. Heeney, T. D. Anthopoulos, J. de Mello, I. McCulloch, Macromolecules 2011, 44, 6649. 13 Z. Fei, R. S. Ashraf, Z. Huang, J. Smith, R. J. Kline, P. D'Angelo, T. D. Anthopoulos, J. R. Durrant, I. McCulloch, M. Heeney, Chem. Commun. 2012, 48, 2955. 14 Q. Zheng, B. J. Jung, J. Sun, H. E. Katz, J. Am. Chem. Soc. 2010, 132, 5394. 15 J.-Y. Wang, S. K. Hau, H.-L. Yip, J. A. Davies, K.-S. Chen, Y. Zhang, Y. Sun, A. K.-Y. Jen, Chem. Mater. 2011, 23, 765. 16 J.-S. Wu, Y.-J. Cheng, M. Dubosc, C.-H. Hsieh, C.-Y. Chang, C.-S. Hsu, Chem. Commun. 2010, 46, 3259. 17 Y.-J. Cheng, C.-H. Chen, Y.-S. Lin, C.-Y. Chang, C.-S. Hsu, Chem. Mater. 2011, 23, 5068. 18 Y.-J. Cheng, J.-S. Wu, P.-I. Shih, C.-Y. Chang, P.-C. Jwo, W.-S. Kao, C.-S. Hsu, Chem. Mater. 2011, 23, 2361. 19 C.-Y. Chang, Y.-J. Cheng, S.-H. Hung, J.-S. Wu, W.-S. Kao, C.-H. Lee, C.-S. Hsu, Adv. Mater. 2012, 24, 549. 20 Y.-J. Cheng, S.-W. Cheng, C.-Y. Chang, W.-S. Kao, M.-H. Liao, C.-S. Hsu, Chem. Commun. 2012, 48, 3203. 21 J. Roncali, Macromol. Rapid Commun. 2007, 28, 1761. 22 D. Hertel, U. Scherf, H. Bässler, Adv. Mater. 1998, 10, 1119. 23 C. Schwarz, H. Bässler, I. Bauer, J.-M. Koenen, E. Preis, U. Scherf, A. Köhler, Adv. Mater. 2012, 24, 922. 24 Y.-C. Chen, C.-Y. Yu, Y.-L. Fan, L.-I. Hung, C.-P. Chen, C. Ting, Chem. Commun. 2010, 46, 6503. 25 R. S. Ashraf, Z. Chen, D. S. Leem, H. Bronstein, W. Zhang, B. Schroeder, Y. Geerts, J. Smith, S. Watkins, T. D. Anthopoulos, H. Sirringhaus, J. C. de Mello, M. Heeney, I. McCulloch, Chem. Mater. 2010, 23, 768. 26 M. Zhang, X. Guo, X. Wang, H. Wang, Y. Li, Chem. Mater. 2011, 23, 4264. 27 X. Wang, H. Luo, Y. Sun, M. Zhang, X. Li, G. Yu, Y. Liu, Y. Li, H. Wang, J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 371. 28 J.-S. Wu, Y.-J. Cheng, T.-Y. Lin, C.-Y. Chang, P.-I. Shih, C.-S. Hsu, Adv. Funct. Mater. 2012, 22, 1711. 29 T. W. Lee, N. S. Kang, J. W. Yu, M. H. Hoang, K. H. Kim, J.-I. Jin, D. H. Choi, J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5921. 30 M. Yuan, P. Yang, M. M. Durban, C. K. Luscombe, Macromolecules 2012, 45, 5934. 31 Y. Zhang, J. Zou, H.-L. Yip, Y. Sun, J. A. Davies, K.-S. Chen, O. Acton, A. K.-Y. Jen, J. Mater. Chem. 2011, 21, 3895. 32 K.-S. Chen, Y. Zhang, H.-L. Yip, Y. Sun, J. A. Davies, C. Ting, C.-P. Chen, A. K.-Y. Jen, Org. Electron. 2011, 12, 794. 33 Y. Sun, S.-C. Chien, H.-L. Yip, Y. Zhang, K.-S. Chen, D. F. Zeigler, F.-C. Chen, B. Lin, A. K.-Y. Jen, J. Mater. Chem. 2011, 21. 34 Y. Zhang, S.-C. Chien, K.-S. Chen, H.-L. Yip, Y. Sun, J. A. Davies, F.-C. Chen, A. K.-Y. Jen, Chem. Commun. 2011, 47, 11026. 35 Y. Zhang, J. Zou, H.-L. Yip, K.-S. Chen, J. A. Davies, Y. Sun, A. K.-Y. Jen, Macromolecules 2011, 44, 4752. 36 Y. Zhang, J. Zou, H.-L. Yip, K.-S. Chen, D. F. Zeigler, Y. Sun, A. K.-Y. Jen, Chem. Mater. 2011, 23, 2289. 37 Y. Sun, S.-C. Chien, H.-L. Yip, K.-S. Chen, Y. Zhang, J. A. Davies, F.-C. Chen, B. Lin, A. K.-Y. Jen, J. Mater. Chem. 2012, 22, 5587. 38 K. M. O'Malley, C.-Z. Li, H.-L. Yip, A. K.-Y. Jen, Adv. Energy Mater. 2012, 2, 82. 39 H. Zhou, L. Yang, A. C. Stuart, S. C. Price, S. Liu, W. You, Angew. Chem. Int. Ed. 2011, 50, 2995. 40 S. C. Price, A. C. Stuart, L. Yang, H. Zhou, W. You, J. Am. Chem. Soc. 2011, 133, 4625. 41 B. C. Schroeder, Z. Huang, R. S. Ashraf, J. Smith, P. D'Angelo, S. E. Watkins, T. D. Anthopoulos, J. R. Durrant, I. McCulloch, Adv. Funct. Mater. 2012, 22, 1663. 42 N. S. Baek, S. K. Hau, H.-L. Yip, O. Acton, K.-S. Chen, A. K.-Y. Jen, Chem. Mater. 2008, 20, 5734. 43 H. Bronstein, Z. Chen, R. S. Ashraf, W. Zhang, J. Du, J. R. Durrant, P. Shakya Tuladhar, K. Song, S. E. Watkins, Y. Geerts, M. M. Wienk, R. A. J. Janssen, T. Anthopoulos, H. Sirringhaus, M. Heeney, I. McCulloch, J. Am. Chem. Soc. 2011, 133, 3272. 44 I. McCulloch, M. Heeney, C. Bailey, K. Genevicius, I. MacDonald, M. Shkunov, D. Sparrowe, S. Tierney, R. Wagner, W. Zhang, M. L. Chabinyc, R. J. Kline, M. D. McGehee, M. F. Toney, Nat. Mater. 2006, 5, 328. 45 K.-T. Wong, T.-C. Chao, L.-C. Chi, Y.-Y. Chu, A. Balaiah, S.-F. Chiu, Y.-H. Liu, Y. Wang, Org. Lett. 2006, 8, 5033. 46 R. Mondal, S. Ko, J. E. Norton, N. Miyaki, H. A. Becerril, E. Verploegen, M. F. Toney, J.-L. Bredas, M. D. McGehee, Z. Bao, J. Mater. Chem. 2009, 19, 7195. 47 L. Pandey, C. Risko, J. E. Norton, J.-L. Brédas, Macromolecules 2012, 45, 6405. Citing Literature Volume24, Issue47December 11, 2012Pages 6356-6361 ReferencesRelatedInformation