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Synthesis and Characterization of Cyclopentadithiophene and Thienothiophene-Based Polymers for Organic Thin-Film Transistors and Solar Cells

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Abstract

Novel donor-donor type alternating copolymers (8CDT-TT and 16CDT-TT) derived from cyclopentadithiophene (CDT) and thienothiophene (TT) moieties that differ from solubilizing side chains were successfully synthesized and characterized. After the synthesis of CDT-TT-based conjugated polymers with dioctyl and dihexadecyl side chains, their optical, thermal, structural and semiconducting properties were investigated. Organic thin-film transistors fabricated from 8CDT-TT and 16CDT-TT exhibit carrier mobilities as high as 3.92×10-4 and 1.05×10-3 cm2V-1s-1, respectively. Bulk heterojunction solar cells fabricated using a polymer:PCBM blend ratio of 1:3 exhibit power conversion efficiencies of 2.12 and 1.84% for 8CDT-TT and 16CDT-TT, respectively.

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References

  1. H. Yan, Z. Chen, Y. Zheng, C. Newman, J. R. Quinn, F. Dötz, M. Castler, and A. Fachetti, Nature, 457, 679 (2009).

    Article  CAS  PubMed  Google Scholar 

  2. H. N. Tsao, D. Cho, J. W. Andreasen, A. Rouhanipour, D. W. Breiby, W. Pisula, and K. Müllen, Adv. Mater., 21, 209 (2009).

    Article  CAS  Google Scholar 

  3. M. J. Lee, D. Gupta, N. Zhao, M. Heeney, I. McCulloch, and H. Sirringhaus, Adv. Funct. Mater., 21, 932 (2011).

    Article  CAS  Google Scholar 

  4. Y. Jiang, Y. Gao, H. Tian, J. Ding, D. Yan, Y. Geng, and F. Wang, Macromolecules, 49, 2135 (2016).

    Article  CAS  Google Scholar 

  5. K. Shi, W. Zhang, X. Liu, Y. Zou, and G. Yu. Polymer, 112, 180 (2017).

    Article  CAS  Google Scholar 

  6. H. Y. Chen, J. Hou, S. Zhang, Y. Liang, G. Yang, Y. Yang, L. Yu, Y. Wu, and G. Li, Nat. Photonics, 3, 649 (2009).

    Article  CAS  Google Scholar 

  7. 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, and I. J. McCulloch, J. Am. Chem. Soc., 133, 3272 (2011).

    Article  CAS  PubMed  Google Scholar 

  8. J. E. Anthony, Chem. Mater., 23, 583 (2011).

    Article  CAS  Google Scholar 

  9. H.-S. Lee, J. S. Lee, A.-H. Jung, W. Cha, H. Kim, H. J. Son, J. H. J. Cho, and B. S. Kim, Polymer, 105, 79 (2016).

    Article  CAS  Google Scholar 

  10. J. Y. Kim, Y. U. Kim, H. J. Kim, H. A. Um, J. Shin, M. J. Cho, and D. H. Choi, Macromol. Res., 24, 980 (2017).

    Article  CAS  Google Scholar 

  11. J. Tong, J. Li, P. Zhang, X. Ma, M. Wang, L. An, J. Sun, P. Guo, C. Yang, and Y. Xia, Polymer, 121, 183 (2017).

    Article  CAS  Google Scholar 

  12. H. Cheon, Y. J. Kim, M. C. Hwang, J. Hong, T. K. An, S.-K. Kwon, Y.-H. Kim, Macromol. Res., 26, 29 (2018).

    Article  CAS  Google Scholar 

  13. C. J. Lim, Y. Lei, B. Wu, L. Li, X. Liu, Y. Lu, F. Zhu, B.S. Ong, X. Hu, and S. C. Ng, Tetrahedron Lett., 57, 1430 (2016).

    Article  CAS  Google Scholar 

  14. A. Facchetti, Chem. Mater., 23, 733 (2011).

    Article  CAS  Google Scholar 

  15. P. K. Madathil, B. Heinrich, B. Donnio, F. Mathevet, J.-L. Face, D. Guillon, A. J. Attias, C. Lee, and K.-S. Lee, J. Nanosci. Nanotechnol., 10, 6800 (2010).

    Article  CAS  PubMed  Google Scholar 

  16. P. K. Madathil, J.-G. Lim, T.-D. Kim, D. Beckmann, A. Mavrinskiy, W. Pisula, M. Baumgarten, K. Müllen, and K.-S. Lee, J. Nanosci. Nanotechnol., 12, 4269 (2012).

    Article  CAS  PubMed  Google Scholar 

  17. H. Huang, J. Youn, R. Ponce Ortiz, Y. Zheng, A. Facchetti, and T. Marks, Chem. Mater., 23, 2185 (2011).

    Article  CAS  Google Scholar 

  18. L. De Cremer, S. Vandeleene, M. Maesen, T. Verbiest, and G. Koeckelberghs, Macromolecules, 41, 591 (2008).

    Article  CAS  Google Scholar 

  19. H. N. Tsao, D.M. Cho, I. Park, M. R. Hansen, A. Mavrinskiy, D.Y. Yoon, R. Graf, W. Pisula, H. W. Spiess, and K. Müllen, J. Am. Chem. Soc., 133, 2605 (2011).

    Article  CAS  PubMed  Google Scholar 

  20. Z. Li, J. Ding, N. Song, J. Lu, and Y. Tao, J. Am. Chem. Soc., 132, 13160 (2010).

    Article  CAS  PubMed  Google Scholar 

  21. J. T. Rogers, K. Schmidt, M. F. Toney, E. J. Kramer, and G. C. Bazan, Adv. Mater., 23, 2284 (2011).

    Article  CAS  PubMed  Google Scholar 

  22. 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, and M. F. Toney, Nat. Mater., 5, 328 (2006).

    Article  CAS  PubMed  Google Scholar 

  23. Z. Li, L. Huo, X. Guo, W. Yong, S. Zhang, and H. Fan, Polymer, 54, 6150 (2013).

    Article  CAS  Google Scholar 

  24. D. Chandran, T. Marszalek, W. Zajaczkowski, P. K. Madathil, R. K. Vijayaraghavan, Y.-H. Koh, S.-Y. Park, J. R. Ochsmann, W. Pisula, and K.-S. Lee, Polymer, 73, 205 (2015).

    Article  CAS  Google Scholar 

  25. H. Wang, Y. Zhu, Z. Liu, L. Zhang, J. Chen, and Y. Cao, Org. Electron., 31, 1 (2016).

    Article  CAS  Google Scholar 

  26. C. Gao, Z. Qiao, K. Shi, S. Chen, Y. Li, G. Yu, X. Li, and H. Wang, Org. Electron., 38, 245 (2016).

    Article  CAS  Google Scholar 

  27. F. Yang, C. Li, J. Zhang, G. Feng, Z. Wei, and W. Li, Org. Electron., 37, 366 (2016).

    Article  CAS  Google Scholar 

  28. I.-B. Kim, D. Khim, S.-Y. Jang, J. Kim, B.-K. Yu, Y.-A Kim, and D.-Y. Kim, Org. Electron., 26, 251 (2015).

    Article  CAS  Google Scholar 

  29. J. R. Ochsmann, D. Chandran, D. W. Gehrig, H. Anwar, P. K. Madathil, K.-S. Lee, and F. Laquai, Macromol. Rapid Commun., 36, 1122 (2015).

    Article  CAS  PubMed  Google Scholar 

  30. S.-Y. Jang, I.-B. Kim, J. Kim, D. Khim, E. Jung, B. Kang, B. Lim, Y.-A Kim, Y. H. Jang, K. Cho, and Dong-Yu Kim, Chem. Mater., 26, 6907 (2014).

    Article  CAS  Google Scholar 

  31. Z. Fei, P. Pattanasattayavong, Y. Han, B. C. Schroeder, F. Yan, R. J. Kline, T. D. Anthopoulos, and M. Heeney, J. Am. Chem. Soc., 136, 15154 (2014).

    Article  CAS  PubMed  Google Scholar 

  32. Y.-H. Ha, J. E. Lee, M.-C. Hwang, Y. J. Kim, J.-H. Lee, C. E. Park, Y.-H. Kim, Macromol. Res., 24, 457 (2016).

    Article  CAS  Google Scholar 

  33. L. S. Fuller, B. Iddon, and K. A. Smith, J. Chem. Soc., Perkin Trans. 1, 1997, 3465.

  34. P. Coppo, C. Domenico, S. G. Yeates, and M. L. Turner, Macromolecules, 36, 2705 (2003).

    Article  CAS  Google Scholar 

  35. E. Lim, B. J. Jung, J. Lee, H. K. Shim, J. I. Lee, Y. S. Yang, and L. M. Do, Macromolecules, 38, 4531 (2005).

    Article  CAS  Google Scholar 

  36. J. Peet, J. Kim, NE. Coates, W. L. Ma, D. Moses, A. J. Heeger, and G. C. Bazan, Nat. Mater., 6, 497 (2007).

    Article  CAS  PubMed  Google Scholar 

  37. G. Li, V. Shrotriya, J. Huang, Y. Yao, T. Moriarty, K. Emery, and Y. Yang, Nat. Mater., 4, 864 (2005).

    Article  CAS  Google Scholar 

  38. Y. Li, Y. Chen, X. Liu, Z. Wang, X. Yang, Y. Tu, and X. Zhu, Macromolecules, 44, 6370 (2011).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Advanced Materials, Hannam University, Daejeon, 34054, Korea

    Pramod Kandoth Madathil, Sinil Choi, Tae-Dong Kim & Kwang-Sup Lee

  2. Department of Physics and EHSRC, University of Ulsan, Ulsan, 44610, Korea

    Shinuk Cho

  3. Department of Chemistry, Christ University, Bangalore, 560029, India

    Pramod Kandoth Madathil

Authors
  1. Pramod Kandoth Madathil
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  2. Shinuk Cho
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  3. Sinil Choi
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  4. Tae-Dong Kim
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  5. Kwang-Sup Lee
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Corresponding author

Correspondence to Kwang-Sup Lee.

Additional information

Acknowledgments: This research was supported by the Asian Office of Aerospace Research and development (AOARD FA2386-17-1-4060) and the Mid-Career Researcher Program (2016R1A2B4008473) through the National Research Foundation of Korea (NRF) funded by the MEST. A part of this research conducted at the University of Ulsan was supported by a National Research Foundation of Korea grant (2014R1A4A1071686). T.-D. Kim also acknowledges the Leading Human Resource Training Program (2016H1D5A1911217).

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Madathil, P.K., Cho, S., Choi, S. et al. Synthesis and Characterization of Cyclopentadithiophene and Thienothiophene-Based Polymers for Organic Thin-Film Transistors and Solar Cells. Macromol. Res. 26, 934–941 (2018). https://doi.org/10.1007/s13233-018-6130-0

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  • DOI: https://doi.org/10.1007/s13233-018-6130-0

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