Citation: GUO Xia, FAN Qunping, CUI Chaohua, ZHANG Zhiguo, ZHANG Maojie. Wide Bandgap Random Terpolymers for High Efficiency Halogen-Free Solvent Processed Polymer Solar Cells[J]. Acta Physico-Chimica Sinica, ;2018, 34(11): 1279-1285. doi: 10.3866/PKU.WHXB201804098 shu

Wide Bandgap Random Terpolymers for High Efficiency Halogen-Free Solvent Processed Polymer Solar Cells

  • Corresponding author: ZHANG Maojie, mjzhang@suda.edu.cn
  • Received Date: 29 March 2018
    Revised Date: 2 April 2018
    Accepted Date: 2 April 2018
    Available Online: 9 November 2018

    Fund Project: The project was supported by the National Natural Science Foundation of China (51573120, 51503135, 51773142, 91633301), and Jiangsu Provincial Natural Science Foundation, China (BK20150332)the National Natural Science Foundation of China 51773142the National Natural Science Foundation of China 51573120the National Natural Science Foundation of China 51503135Jiangsu Provincial Natural Science Foundation, China BK20150332the National Natural Science Foundation of China 91633301

  • Over the past two decades, bulk heterojunction polymer solar cells (PSCs) have attracted significant attention owing to their potential applications in the mass fabrication of flexible device panels by roll-to-roll printing. To improve the photovoltaic performance of PSCs, much effort has been devoted to the optimization of properties of donor-acceptor (D-A) type polymer donor materials. Until now, the development of high-performance donor polymers is mainly dependent on the design and synthesis of binary polymers with a regular D/A alternating skeleton. Compared to binary polymers, random terpolymers with three different donor or acceptor monomer units possess synergetic effects of their inherent properties, such as optical absorption ability, energy levels, crystallinity, charge mobility, and morphological compatibility with the n-OS acceptors with suitable adjustment of the molar ratio of the three monomers. However, the irregularity in the polymer backbone of the random terpolymers may have an adverse effect on molecular packing, crystallinity, and charge mobility. Therefore, design and synthesis of high-performance terpolymers for PSCs is a challenging task. In this study, a series of wide bandgap random terpolymers PSBTZ-80, PSBTZ-60, and PSBTZ-40 based on alkylthiothienyl substituted benzodithiophene as the donor unit and two weak electron-deficient acceptor units of 5, 6-difluorobenzotriazole (FBTz) and thiazolothiazole (TTz) were designed and synthesized for PSC applications. The optical, electrochemical, molecular packing, and photovoltaic properties of the polymers were effectively modulated by varying the FBTz:TTz molar ratio. Therefore, the PSC based on PSBTZ-60 as the donor material and narrow bandgap small molecule 3, 9-bis(2-methylene-(3-(1, 1-dicyanomethylene)-indanone))-5, 5, 11, 11-tetrakis(4-hexyl-phenyl)-dithieno[2, 3-d:2', 3'-d']-s-indaceno[1, 2-b:5, 6-b']di thiophene) (ITIC) as the acceptor, processed using halogen-free solvents, exhibited high power conversion efficiency (PCE) of 10.3% with high open-circuit voltage (Voc) of 0.91 V, improved short-circuit current density (Jsc) of 18.0 mA∙cm−2, and fill factor (FF) of 62.7%, which are superior to those of PSCs based on binary polymers PSBZ (a PCE of 8.1%, Voc of 0.89 V, Jsc of 14.7 mA∙cm−2, and FF of 61.5%) and PSTZ (a PCE of 8.5%, Voc of 0.96 V, Jsc of 14.9 mA∙cm−2, and FF of 59.1%). These results indicate that random terpolymerization is a simple and practical strategy for the development of high-performance polymer photovoltaic materials.
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    1. [1]

      Hou, J.; Ingan s, O.; Friend, R. H.; Gao, F. Nat. Mater. 2018, 17, 119. doi: 10.1038/nmat5063  doi: 10.1038/nmat5063

    2. [2]

      Lin, Y.; Zhan, X. Adv. Energy Mater. 2015, 5, 1501063.doi: 10.1002/aenm.201501063  doi: 10.1002/aenm.201501063

    3. [3]

      Zhang, Z. G.; Yang, Y.; Yao, J.; Xue, L.; Chen, S.; Li, X.; Morrison, W.; Yang, C.; Li, Y. Angew. Chem. Int. Ed. 2017, 56, 13503.doi: 10.1002/anie.201707678  doi: 10.1002/anie.201707678

    4. [4]

      Fan, B.; Ying, L.; Zhu, P.; Pan, F.; Liu, F.; Chen, J.; Huang, F.; Cao, Y. Adv. Mater. 2017, 29, 1703906. doi: 10.1002/adma.201703906  doi: 10.1002/adma.201703906

    5. [5]

      Xu, Z.; Fan, Q.; Meng, X.; Guo, X.; Su, W.; Ma, W.; Zhang, M.; Li, Y. Chem. Mater. 2017, 29, 4811.doi: 10.1021/acs.chemmater.7b00729  doi: 10.1021/acs.chemmater.7b00729

    6. [6]

      Li, S.; Liu, W.; Shi, M.; Mai, J.; Lau, T. K.; Wan, J.; Lu, X.; Li, C. Z.; Chen, H. Energy Environ. Sci. 2016, 9, 604. doi: 10.1039/c5ee03481g  doi: 10.1039/c5ee03481g

    7. [7]

      Fei, Z.; Eisner, F. D.; Jiao, X.; Azzouzi, M.; R hr, J. A.; Han, Y.; Shahid, M.; Chesman, A. S. R.; Easton, C. D.; McNeill, C. R.; et al. Adv. Mater. 2018, 30, 1705209. doi: 10.1002/adma.201705209  doi: 10.1002/adma.201705209

    8. [8]

      Zhao, W.; Li, S.; Yao, H.; Zhang, S.; Zhang, Y.; Yang, B.; Hou, J.J. Am. Chem. Soc. 2017, 139, 7148. doi: 10.1021/jacs.7b02677  doi: 10.1021/jacs.7b02677

    9. [9]

      Fan, Q.; Su, W.; Wang, Y.; Guo, B.; Jiang, Y.; Guo, X.; Liu, F.; Thomas, P. R.; Zhang, M. J.; Li, Y. F. Sci. China Chem. 2018, doi: 10.1007/s11426-017-9199-1  doi: 10.1007/s11426-017-9199-1

    10. [10]

      Lin, Y.; Wang, J.; Zhang, Z. G.; Bai, H.; Li, Y.; Zhu, D.; Zhan, X. Adv. Mater. 2015, 27, 1170. doi: 10.1002/adma.201404317  doi: 10.1002/adma.201404317

    11. [11]

      Xu, X.; Yu, T.; Bi, Z.; Ma, W.; Li, Y.; Peng, Q. Adv. Mater. 2017, 30, 1703973. doi: 10.1002/adma.201703973  doi: 10.1002/adma.201703973

    12. [12]

      Lin, Y.; Zhang, Z.; Bai, H.; Wang, J.; Yao, Y.; Li, Y.; Zhu, D.; Zhan, X. Energy Environ. Sci. 2015, 8, 610. doi: 10.1039/c4ee03424d  doi: 10.1039/c4ee03424d

    13. [13]

      Dai, S.; Zhao, F.; Zhang, Q.; Lau, T. K.; Li, T.; Liu, K.; Ling, Q.; Wang, C.; Lu, X.; You, W.; et al. J. Am. Chem. Soc. 2017, 139, 1336. doi: 10.1021/jacs.6b12755  doi: 10.1021/jacs.6b12755

    14. [14]

      Liu, Y.; Zhang, Z.; Feng, S.; Li, M.; Wu, L.; Hou, R.; Xu, X.; Chen, X.; Bo, Z. J. Am. Chem. Soc. 2017, 139, 3356.doi: 10.1021/jacs.7b00566  doi: 10.1021/jacs.7b00566

    15. [15]

      Shi, X.; Chen, J.; Gao, K.; Zuo, L.; Yao, Z.; Liu, F.; Tang, J.; Jen, A. K. Y. Adv. Energy Mater. 2018, doi: 10.1002/aenm.201702831  doi: 10.1002/aenm.201702831

    16. [16]

      Kan, B.; Zhang, J.; Liu, F.; Wan, X.; Li, C.; Ke, X.; Wang, Y.; Feng, H.; Zhang, Y.; Long, G.; et al. Adv. Mater. 2017, 30, 1704904.doi: 10.1002/adma.201704904  doi: 10.1002/adma.201704904

    17. [17]

      Luo, Z.; Bin, H.; Liu, T.; Zhang, Z.; Yang, Y.; Zhong, C.; Qiu, B.; Li, G.; Gao, W.; Xie, D.; et al. Adv. Mater. 2018, doi: 10.1002/adma.201706124  doi: 10.1002/adma.201706124

    18. [18]

      Li, Y.; Lin, J. D.; Che, X.; Qu, Y.; Liu, F.; Liao, L. S.; Forrest, S. R.J. Am. Chem. Soc. 2017, 139, 17114. doi: 10.1021/jacs.7b11278  doi: 10.1021/jacs.7b11278

    19. [19]

      Zhou, Z.; Liu, W.; Zhang, Z.; Liu, F.; Yan, H.; Zhu, X. Adv. Mater. 2017, 29, 1704510. doi: 10.1002/adma.201704510  doi: 10.1002/adma.201704510

    20. [20]

      Yang, Y.; Zhang, Z.; Bin, H.; Chen, S.; Gao, L.; Xue, L.; Yang, C.; Li, Y. J. Am. Chem. Soc. 2016, 138, 15011. doi: 10.1021/jacs.6b09110  doi: 10.1021/jacs.6b09110

    21. [21]

      Zhao, W.; Qian, D.; Zhang, S.; Li, S.; Ingan s, O.; Gao, F.; Hou, J. Adv. Mater. 2016, 28, 4734. doi: 10.1002/adma.201600281  doi: 10.1002/adma.201600281

    22. [22]

      Bin, H.; Zhang, Z. G.; Gao, L.; Chen, S.; Zhong, L.; Xue, L.; Yang, C.; Li, Y. J. Am. Chem. Soc. 2016, 138, 4657.doi: 10.1021/jacs.6b01744  doi: 10.1021/jacs.6b01744

    23. [23]

      Xue, L.; Yang, Y.; Xu, J.; Zhang, C.; Bin, H.; Zhang, Z. G.; Qiu, B.; Li, X.; Sun, C.; Gao, L.; et al. Adv. Mater. 2017, 29, 1703344.doi: 10.1002/adma.201703344  doi: 10.1002/adma.201703344

    24. [24]

      Bin, H.; Gao, L.; Zhang, Z. G.; Yang, Y.; Zhang, Y.; Zhang, C.; Chen, S.; Xue, L.; Yang, C.; Xiao, M.; Li, Y. Nat. Commun. 2016, 7, 13651. doi: 10.1038/ncomms13651  doi: 10.1038/ncomms13651

    25. [25]

      Fan, Q.; Su, W.; Guo, X.; Wang, Y.; Chen, J.; Ye, C.; Zhang, M.; Li, Y. J. Mater. Chem. A 2017, 5, 9204. doi: 10.1039/c7ta02075a  doi: 10.1039/c7ta02075a

    26. [26]

      Fan, Q.; Su, W.; Meng, X.; Guo, X.; Li, G.; Ma, W.; Zhang, M.; Li, Y. Sol. RRL 2017, 1, 1700020. doi: 10.1002/solr.201700020  doi: 10.1002/solr.201700020

    27. [27]

      Fan, Q.; Wang, Y.; Zhang, M.; Wu, B.; Guo, X.; Jiang, Y.; Li, W.; Guo, B.; Ye, C.; Su, W.; et al. Adv. Mater. 2018, 30, 1704546.doi: 10.1002/adma.201704546  doi: 10.1002/adma.201704546

    28. [28]

      Wang, Y.; Fan, Q.; Guo, X.; Li, W.; Guo, B.; Su, W.; Ou, X.; Zhang, M, J. Mater. Chem. A 2017, 5, 22180. doi: 10.1039/c7ta07785h  doi: 10.1039/c7ta07785h

    29. [29]

      Su, W.; Fan, Q.; Guo, X.; Meng, X.; Bi, Z.; Ma, W.; Zhang, M.; Li, Y. Nano Energy 2017, 38, 510. doi: 10.1016/j.nanoen.2017.05.060  doi: 10.1016/j.nanoen.2017.05.060

    30. [30]

      Guo, B.; Li, W.; Guo, X.; Meng, X.; Ma, W.; Zhang, M.; Li, Y. Adv. Mater. 2017, 29, 1702291. doi: 10.1002/adma.201702291  doi: 10.1002/adma.201702291

    31. [31]

      Chen, S.; Liu, Y.; Zhang, L.; Chow, P. C. Y.; Wang, Z.; Zhang, G.; Ma, W.; Yan, H. J. Am. Chem. Soc. 2017, 139, 6298.doi: 10.1021/jacs.7b01606  doi: 10.1021/jacs.7b01606

    32. [32]

      Liu, D.; Wang, J.; Gu, C.; Li, Y.; Bao, X.; Yang, R. Adv. Mater. 2018, 30, 1705870. doi: 10.1002/adma.201705870  doi: 10.1002/adma.201705870

    33. [33]

      Kang, T. E.; Kim, K. H.; Kim, B. J. J. Mater. Chem. A 2014, 2, 15252. doi: 10.1039/c4ta02426e  doi: 10.1039/c4ta02426e

    34. [34]

      Duan, C.; Gao, K.; Franeker, J. J.; Liu, F.; Wienk, M. M.; Janssen, R. A. J. J. Am. Chem. Soc. 2016, 138, 10782. doi: 10.1021/jacs.6b06418  doi: 10.1021/jacs.6b06418

    35. [35]

      Fan, Q.; Liu, Y.; Xiao, M.; Su, W.; Gao, H.; Chen, J.; Tan, H.; Wang, Y.; Yang, R.; Zhu, W. J. Mater. Chem. C 2015, 3, 6240.doi: 10.1039/c5tc00785b  doi: 10.1039/c5tc00785b

    36. [36]

      Fan, Q.; Xu, X.; Liu, Y.; Su, W.; He, X.; Zhang, Y.; Tan, H.; Wang, Y.; Peng, Q.; Zhu, W. Polym. Chem. 2016, 7, 1747.doi: 10.1039/c5py01985k  doi: 10.1039/c5py01985k

    37. [37]

      Chen, S.; Cho, H. J.; Lee, J.; Yang, Y.; Zhang, Z. G.; Li, Y.; Yang, C. Adv. Energy Mater. 2017, 7, 1701125. doi: 10.1002/aenm.201701125  doi: 10.1002/aenm.201701125

    38. [38]

      Zhang, M.; Guo, X.; Zhang, S.; Hou, J. Adv. Mater. 2014, 26, 1118. doi: 10.1002/adma.201304427  doi: 10.1002/adma.201304427

    39. [39]

      Fan, Q.; Su, W.; Guo, X.; Guo, B.; Li, W.; Zhang, Y.; Wang, K.; Zhang, M.; Li, Y. Adv. Energy Mater. 2016, 6, 1600430.doi: 10.1002/aenm.201600430  doi: 10.1002/aenm.201600430

    40. [40]

      Zhang, M.; Guo, X.; Ma, W.; Ade, H.; Hou, J. Adv. Mater. 2015, 27, 4655. doi: 10.1002/adma.201502110  doi: 10.1002/adma.201502110

    41. [41]

      Blom, P. W.; Mihailetchi, V. D.; Koster, L. J.; Markov. D. E. Adv. Mater. 2007, 19, 1551. doi: 10.1002/adma.200601093  doi: 10.1002/adma.200601093

    42. [42]

      Fan, Q.; Xu, Z.; Guo, X.; Meng, X.; Li, W.; Su, W.; Ou, X.; Ma, W.; Zhang, M.; Li, Y. Nano Energy 2017, 40, 20.doi: 10.1016/j.nanoen.2017.07.047  doi: 10.1016/j.nanoen.2017.07.047

    43. [43]

      Fan, Q.; Su, W.; Guo, X.; Zhang, X.; Xu, Z.; Guo, B.; Jiang, L.; Zhang M.; Li Y. J. Mater. Chem. A 2017, 5, 5106.doi: 10.1039/c6ta11240d  doi: 10.1039/c6ta11240d

    44. [44]

      Fan, Q.; Zhu, Q.; Xu, Z.; Su, W.; Chen, J.; Wu, J.; Guo, X.; Ma, W.; Zhang, M.; Li, Y. Nano Energy 2018, 48, 413.doi: 10.1016/j.nanoen.2018.04.002  doi: 10.1016/j.nanoen.2018.04.002

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