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Synthesis and characterization of new TPD-based copolymers and applications in bulk heterojunction solar cells

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Abstract

We developed and synthesized two novel polymeric semiconductor materials containing thienopyrrolodione (TPD) units, with one of the polymers also containing thiophene (T) units and the other containing bi-thiophene (BT) units, and denoted as TPD-T and TPD-BT, respectively. TPD-T and TPD-BT were studied for bulk heterojunction organic solar cells as blends with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). The TPD-T-based device exhibited considerably better photovoltaic performances, with a power conversion efficiency of 2.51%, in contrast to the 1.63% value for the TPD-BT-based device. According to atomic force microscope images of the TPD-BT:PC71BM and TPD-T:PC71BM blend films, the latter showed more nanoscale phase aggregation, explaining its better photovoltaic properties.

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References

  1. G. B. Lee, R. Kim, H.-J. Cha, C. E. Park, J. H. Kim, and Y.-H. Kim, Macromol. Res., 22, 569 (2014).

    Article  CAS  Google Scholar 

  2. K. Nakano, M. Nakano, B. Xiao, E. Zhou, K. Suzuki, I. Osaka, K. Takimiya, and K. Tajima, Macromolecules, 49, 1752 (2016).

    Article  CAS  Google Scholar 

  3. I. Etxebarria, J. Ajuria, and R. Pacios, Org. Electron., 19, 34 (2015).

    Article  CAS  Google Scholar 

  4. K. Zhang, Z. Hu, C. Sun, Z. Wu, F. Huang, and Y. Cao, Chem. Mater., 29, 141 (2017).

    Article  CAS  Google Scholar 

  5. G. A. dos Reis Benatto, B. Roth, M. Corazza, R. R. Søndergaard, S. A. Gevorgyan, M. Jørgensen, and F. C. Krebs, Nanoscale, 8, 318 (2016).

    Article  CAS  Google Scholar 

  6. K. Liu, T. T. Larsen-Olsen, Y. Lin, M. Beliatis, E. Bundgaard, M. Jørgensen, F. C. Krebs, and X. Zhan, J. Mater. Chem. A, 4, 1044 (2016).

    Article  CAS  Google Scholar 

  7. J. W. Jung, J. W. Jo, C. C. Chueh, F. Liu, W. H. Jo, T. P. Russell, and A. K. Y. Jen, Adv. Mater., 27, 3310 (2015).

    Article  CAS  Google Scholar 

  8. W. Li, W. Roelofs, M. Turbiez, M. M. Wienk, and R. A. Janssen, Adv. Mater., 26, 3304 (2014).

    Article  CAS  Google Scholar 

  9. J. Hong, Y. J. Kim, Y. H. Kim, and C. E. Park, Macromol. Chem. Phys., 217, 2116 (2016).

    Article  CAS  Google Scholar 

  10. B. W. Larson, O. G. Reid, D. C. Coffey, S. M. Avdoshenko, A. A. Popov, O. V. Boltalina, S. H. Strauss, N. Kopidakis, and G. Rumbles, Adv. Energy Mater., 6, 1601427 (2016).

    Article  Google Scholar 

  11. N. Banerji, Nat. Mater., 16, 503 (2017).

    Article  CAS  Google Scholar 

  12. Q.-Y. Li, J. Xiao, L.-M. Tang, H.-C. Wang, Z. Chen, Z. Yang, H.-L. Yip, and Y.-X. Xu, Org. Electron., 44, 217 (2017).

    Article  CAS  Google Scholar 

  13. X. Guo, N. Zhou, S. J. Lou, J. W. Hennek, R. Ponce Ortiz, M. R. Butler, P.-L. T. Boudreault, J. Strzalka, P.-O. Morin, and M. Leclerc, J. Am. Chem. Soc., 134, 18427 (2012).

    Article  CAS  Google Scholar 

  14. W. S. Yang, J. H. Noh, N. J. Jeon, Y. C. Kim, S. Ryu, J. Seo, and S. I. Seok, Science, 348, 1234 (2015).

    Article  CAS  Google Scholar 

  15. J. Zhao, Y. Li, G. Yang, K. Jiang, H. Lin, H. Ade, W. Ma, and H. Yan, Nat. Energy, 1, 15027 (2016).

    Article  CAS  Google Scholar 

  16. J. L. Wang, F. Xiao, J. Yan, Z. Wu, K. K. Liu, Z. F. Chang, R. B. Zhang, H. Chen, H. B. Wu, and Y. Cao, Adv. Funct. Mater., 26, 1803 (2016).

    Article  CAS  Google Scholar 

  17. J.-L. Wang, K.-K. Liu, J. Yan, Z. Wu, F. Liu, F. Xiao, Z.-F. Chang, H.-B. Wu, Y. Cao, and T. P. Russell, J. Am. Chem. Soc., 138, 7687 (2016).

    Article  CAS  Google Scholar 

  18. K. H. Park, Y. J. Kim, G. B. Lee, T. K. An, C. E. Park, S. K. Kwon, and Y. H. Kim, Adv. Funct. Mater., 25, 3991 (2015).

    Article  CAS  Google Scholar 

  19. W.-C. Li, Y.-R. Liu, J.-H. Chen, W.-C. Chang, P.-T. Sah, and L.-H. Chan, Org. Electron., 33, 213 (2016).

    Article  Google Scholar 

  20. Y. J. Kim, Y. J. Lee, J. W. Jang, H. Cha, Y. H. Kim, S. K. Kwon, and C. E. Park, J. Polym. Sci., Part A: Polym. Chem., 51, 4742 (2013).

    Article  CAS  Google Scholar 

  21. M. C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A. J. Heeger, and C. J. Brabec., Adv. Mater., 18, 789 (2006).

    Article  CAS  Google Scholar 

  22. Y.-R. Hong, H.-K. Wong, L. C. Moh, H.-S. Tan, and Z.-K. Chen, Chem. Commun., 47, 4920 (2011).

    Article  CAS  Google Scholar 

  23. J. E. Coughlin, Z. B. Henson, G. C. Welch, and G. C. Bazan, Acc. Chem. Res., 47, 257 (2014).

    Article  CAS  Google Scholar 

  24. Y. Zou, A. Najari, P. Berrouard, S. Beaupré, B. R. Aïch, Y. Tao, and M. Leclerc, J. Am. Chem. Soc., 132, 5330 (2010).

    Article  CAS  Google Scholar 

  25. T.-Y. Chu, J. Lu, S. Beaupré, Y. Zhang, J.-R. Pouliot, S. Wakim, J. Zhou, M. Leclerc, Z. Li, J. Ding, and Y. Tao, J. Am. Chem. Soc., 133, 4250 (2011).

    Article  CAS  Google Scholar 

  26. J. Warnan, C. Cabanetos, A. E. Labban, M. R. Hansen, C. Tassone, M. F. Toney, and P. M. Beaujuge, Adv. Mater., 26, 4357 (2014).

    Article  CAS  Google Scholar 

  27. T. K. An, S. J. Park, E. S. Ahn, S. H. Jang, Y. Kim, K. Kim, H. Cha, Y. J. Kim, S. H. Kim, C. E. Park, and Y.-H. Kim, Dyes Pigment., 114, 60 (2015).

    Article  CAS  Google Scholar 

  28. M.-J. Kim, T. K. An, S.-O. Kim, H. Cha, H. N. Kim, T. Xiofeng, C. E. Park, and Y.-H. Kim, Mater. Chem. Phys., 153, 63, (2015).

    Article  CAS  Google Scholar 

  29. H. Zhou, L. Yang, S. Stoneking, and W. You, ACS Appl. Mater. Interfaces, 2, 1377 (2010).

    Article  CAS  Google Scholar 

  30. H. Goto and K. Akagi, Angew. Chem. Int. Ed., 44, 4322 (2005).

    Article  CAS  Google Scholar 

  31. Y.-J. Cheng, S.-H. Yang, and C.-S. Hsu, Chem. Rev., 109, 5868 (2009).

    Article  CAS  Google Scholar 

  32. S. Yum, T. K. An, X. Wang, W. Lee, M. A. Uddin, Y. J. Kim, T. L. Nguyen, S. Xu, S. Hwang, C. E. Park, and H. Y. Woo, Chem. Mater., 26, 2147 (2014).

    Article  CAS  Google Scholar 

  33. T. K. An, S.-H. Hahn, S. Nam, H. Cha, Y. Rho, D. S. Chung, M. Ree, M. S. Kang, S.-K. Kwon, Y.-H. Kim, and C. E. Park, Dyes Pigm., 96, 756 (2013).

    Article  CAS  Google Scholar 

  34. J. E. Lee, T. K. An, and Y.-H. Kim, Macromol. Res., 24, 629 (2016).

    Article  CAS  Google Scholar 

  35. S. Wen, Q. Dong, W. Cheng, P. Li, B. Xu, and W. Tian, Sol. Energy Mater. Sol. Cells, 100, 239 (2012).

    Article  CAS  Google Scholar 

  36. G. R. Bamwenda and H. Arakawa, J. Mol. Catal. A: Chem., 161, 105 (2000).

    Article  CAS  Google Scholar 

  37. L. Ye, W. Jiang, W. Zhao, S. Zhang, D. Qian, Z. Wang, and J. Hou, Small, 10, 4658 (2014).

    Article  CAS  Google Scholar 

  38. Y. R. Cheon, Y. J. Kim, J.-J. Ha, M.-J. Kim, C. E. Park, and Y.-H. Kim, Macromolecules, 47, 8570 (2014).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry and RIGET, Gyeongsang National University, Jinju, Gyeongnam, 52828, Korea

    Hyungin Cheon & Yun-Hi Kim

  2. POSTECH Organic Electronics Laboratory, Department of Chemical Engineering, Pohang University of Science and Technology, Pohang, Gyeongbuk, 37673, Korea

    Yu Jin Kim & Jisu Hong

  3. Department of Materials Engineering and Convergence Technology & ERI, Gyeongsang National University, Jinju, Gyeongnam, 52828, Korea

    Moon Chan Hwang & Soon-Ki Kwon

  4. Department of Polymer Science & Engineering and Department of IT Convergence, Korea National University of Transportation, 50 Daehak-Ro, Chungju, Chungbuk, 27469, Korea

    Tae Kyu An

Authors
  1. Hyungin Cheon
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  2. Yu Jin Kim
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  3. Moon Chan Hwang
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  4. Jisu Hong
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  5. Tae Kyu An
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  6. Soon-Ki Kwon
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  7. Yun-Hi Kim
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Corresponding authors

Correspondence to Tae Kyu An, Soon-Ki Kwon or Yun-Hi Kim.

Additional information

Acknowledgments: This work was supported by the KETEP by the Korea government Ministry of Knowledge Economy (20123010010140) and NRF (2016M1A2A2940911). This work was also supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (2017R1C1B2002888).

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Cheon, H., Kim, Y.J., Hwang, M.C. et al. Synthesis and characterization of new TPD-based copolymers and applications in bulk heterojunction solar cells. Macromol. Res. 26, 29–34 (2018). https://doi.org/10.1007/s13233-018-6011-6

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  • DOI: https://doi.org/10.1007/s13233-018-6011-6

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