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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(03): 214-222
DOI: 10.1055/s-0040-1713857
Original Article
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2020) The Author(s).

Effects of the Electron-Deficient Third Components in n-Type Terpolymers on Morphology and Performance of All-Polymer Solar Cells

Bin Liu
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
b   School of Advanced Materials, Peking University Shenzhen Graduate School, Peking University, Shenzhen 518055, China
c   Department of Physics, National University of Singapore, 2 Science Drive 3, Singapore 117542, Singapore
,
Huiliang Sun 
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
,
Chang Woo Koh
d   Department of Chemistry, Korea University, Seoul 136-713, South Korea
,
Mengyao Su
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
,
Bao Tu
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
,
Yumin Tang
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
,
Qiaogan Liao
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
,
Junwei Wang
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
,
Wanli Yang
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
,
Hong Meng 
b   School of Advanced Materials, Peking University Shenzhen Graduate School, Peking University, Shenzhen 518055, China
,
Han Young Woo 
d   Department of Chemistry, Korea University, Seoul 136-713, South Korea
,
Xugang Guo 
a   Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong 518055, China
› Author Affiliations Funding Information H.S. thanks NSFC (21801124) for the financial support. X.G. is grateful to the Shenzhen Basic Research Fund (JCYJ20170817105905899) and the Shenzhen Peacock Plan Project (KQTD20140630110339343). H.M. is grateful to the Shenzhen Science and Technology research grant (JCYJ20180302153406868) and Shenzhen Hong Kong Innovation Circle Joint R and D project (SGLH20161212101631809). B.L. thanks China Scholarship Council Fund (No.201906010074). H.Y.W. is grateful for the financial support from the National Research Foundation (NRF) of Korea (2019R1A6A1A11044070).
Further Information

Publication History

Received: 29 April 2020

Accepted after revision: 26 May 2020

Publication Date:
16 July 2020 (online)

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Abstract

Compared with p-type terpolymers, less effort has been devoted to n-type analogs. Herein, we synthesized a series of n-type terpolymers via incorporating three electron-deficient third components including thienopyrroledione (TPD), phthalimide, and benzothiadiazole into an imide-functionalized parent n-type copolymer to tune optoelectronic properties without sacrificing the n-type characteristics. Due to effects of the third components with different electron-accepting ability and solubility, the resulting three polymers feature distinct energy levels and crystallinity. In addition, heteroatoms (S, O, and N) attached on the third components trigger intramolecular noncovalent interactions, which can increase molecule planarity and have a significant effect on the packing structures of the polymer films. As a result, the best power conversion efficiency of 8.28% was achieved from all-polymer solar cells (all-PSCs) based on n-type terpolymer containing TPD. This is contributed by promoted electron mobility and face-on polymer packing, showing the pronounced advantages of the TPD used as a third component for thriving efficient n-type terpolymers. The generality is also successfully validated in a benchmark polymer donor/acceptor system by introducing TPD into the benchmark n-type polymer N2200. The results demonstrate the feasibility of introducing suitable electron-deficient building blocks as the third components for high-performance n-type terpolymers toward efficient all-PSCs.

Key words

n-type terpolymers - electron-deficient building blocks - bulk morphology - imide-functionalized heteroarenes - all-polymer solar cells

Supporting Information

Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1713857.


Supporting Information

 

  • References

  • 1 Heeger AJ. Adv. Mater. 2014; 26: 10
    CrossrefPubMed
    • 2a Yuan J, Zhang Y, Zhou L, Zhang G, Yip H.-L, Lau T.-K, Lu X, Zhu C, Peng H, Johnson PA. Joule 2019; 3: 1140
      CrossrefPubMed
    • 2b Cai F, Zhu C, Yuan J, Li Z, Meng L, Liu W, Peng H, Jiang L, Li Y, Zou Y. Chem. Commun. 2020; 56: 4340
      CrossrefPubMed
    • 2c Li S, Li C.-Z, Shi M, Chen H. ACS Energy Lett. 2020; 5: 1554
      CrossrefPubMed
    • 2d Zhang J, Liu W, Xu S, Zhu X. Org. Mater. 2019; 1: 30
      CrossrefPubMed
    • 2e Liao Q, Kang Q, Yang Y, An C, Xu B, Hou J. Adv. Mater. 2019; 32: 1906557
      CrossrefPubMed
    • 2f Xu X, Feng K, Bi Z, Ma W, Zhang G, Peng Q. Adv. Mater. 2019; 31: 1901872
      CrossrefPubMed
    • 2g Ma R, Liu T, Luo Z, Guo Q, Xiao Y, Chen Y, Li X, Luo S, Lu X, Zhang M. Sci. China Chem. 2020; 63: 325
      CrossrefPubMed
    • 2h An Q, Ma X, Gao J, Zhang F. Sci. Bull. 2019; 64: 504
      CrossrefPubMed
    • 2i Cui Y, Yao H, Zhang J, Zhang T, Wang Y, Hong L, Xian K, Xu B, Zhang S, Peng J. Nat. Commun. 2019; 10: 1
      CrossrefPubMed
    • 2j Guo Q, Ma R, Hu J, Wang Z, Sun H, Dong X, Luo Z, Liu T, Guo X, Guo X. Adv. Funct. Mater. 2020; 30: 2000383
      CrossrefPubMed
    • 2k Yan C, Liu T, Chen Y, Ma R, Tang H, Li G, Li T, Xiao Y, Yang T, Lu X. Solar RRL 2020; 4: 1900377
      CrossrefPubMed
    • 2l Liu T, Gao W, Zhang G, Zhang L, Xin J, Ma W, Yang C, Yan H, Zhan C, Yao J. Solar RRL 2019; 3: 1800376
      CrossrefPubMed
    • 2m Liu L, Kan Y, Gao K, Wang J, Zhao M, Chen H, Zhao C, Jiu T, Jen AK. Y, Li Y. Adv. Mater. 2020; 32: 1907604
      CrossrefPubMed
    • 2n Dong Y, Zou Y, Yuan J, Yang H, Wu Y, Cui C, Li Y. Adv. Mater. 2019; 31: 1904601
      CrossrefPubMed
    • 2o Li K, Wu Y, Li X, Fu H, Zhan C. Sci. China Chem. 2020; 63: 490
      CrossrefPubMed
    • 2p Sun H, Liu T, Yu J, Lau T.-K, Zhang G, Zhang Y, Su M, Tang Y, Ma R, Liu B. Energy Environ. Sci. 2019; 12: 3328
      CrossrefPubMed
    • 3a Zhang K, Xia R, Fan B, Liu X, Wang Z, Dong S, Yip HL, Ying L, Huang F, Cao Y. Adv. Mater. 2018; 30: 1803166
      CrossrefPubMed
    • 3b Wang G, Melkonyan FS, Facchetti A, Marks TJ. Angew. Chem. Int. Ed. 2019; 58: 4129
      CrossrefPubMed
    • 3c Hwang Y.-J, Earmme T, Courtright BA, Eberle FN, Jenekhe SA. J. Am. Chem. Soc. 2015; 137: 4424
      CrossrefPubMed
    • 3d Lee C, Lee S, Kim G.-U, Lee W, Kim BJ. Chem. Rev. 2019; 119: 8028
      CrossrefPubMed
    • 3e Choi J, Kim W, Kim S, Kim T.-S, Kim BJ. Chem. Mater. 2019; 31: 9057
      CrossrefPubMed
    • 3f Feng W, Lin Z, Lin C, Wang W, Ling Q. ACS Appl. Mater. Interfaces 2019; 11: 43441
      CrossrefPubMed
    • 3g Chen S, An Y, Dutta GK, Kim Y, Zhang ZG, Li Y, Yang C. Adv. Funct. Mater. 2017; 27: 1603564
      CrossrefPubMed
    • 3h Fan Q, Su W, Chen S, Kim W, Chen X, Lee B, Liu T, Méndez-Romero UA, Ma R, Yang T. Joule 2020; 4: 658
      CrossrefPubMed
    • 3i Yang J, Xiao B, Tang A, Li J, Wang X, Zhou E. Adv. Mater. 2019; 31: 1804699
      CrossrefPubMed
    • 3j Wang W, Wu Q, Sun R, Guo J, Wu Y, Shi M, Yang W, Li H, Min J. Joule 2020; 4: 1070
      CrossrefPubMed
    • 3k Fan Q, Ma R, Liu T, Su W, Peng W, Zhang M, Wang Z, Wen X, Cong Z, Luo Z. Solar RRL 2020; 4: 2000142
      CrossrefPubMed
    • 3l Wu J, Meng Y, Guo X, Zhu L, Liu F, Zhang M. J. Mater. Chem. A 2019; 7: 16190
      CrossrefPubMed
    • 3m Jia T, Zhang J, Zhong W, Liang Y, Zhang K, Dong S, Ying L, Liu F, Wang X, Huang F. Nano Energy 2020; 72: 104718
      CrossrefPubMed
    • 3n Zhou K, Wu Y, Liu Y, Zhou X, Zhang L, Ma W. ACS Energy Lett. 2019; 4: 1057
      CrossrefPubMed
    • 3o Sun H, Liu B, Koh CW, Zhang Y, Chen J, Wang Y, Chen P, Tu B, Su M, Wang H, Guo X. Adv. Funct. Mater. 2019; 29: 1903970
      CrossrefPubMed
    • 3p Liu X, Li X, Li Y, Song C, Zhu L, Zhang W, Wang HQ, Fang J. Adv. Mater. 2016; 28: 7405
      CrossrefPubMed
    • 4a Guo Y, Li Y, Awartani O, Han H, Zhao J, Ade H, Yan H, Zhao D. Adv. Mater. 2017; 29: 1700309
      CrossrefPubMed
    • 4b Kolhe NB, Lee H, Kuzuhara D, Yoshimoto N, Koganezawa T, Jenekhe SA. Chem. Mater. 2018; 30: 6540
      CrossrefPubMed
    • 4c Zhao R, Wang N, Yu Y, Liu J. Chem. Mater. 2020; 32: 1308
      CrossrefPubMed
    • 4d Liu X, Zhang C, Duan C, Li M, Hu Z, Wang J, Liu F, Li N, Brabec CJ, Janssen RA, Bazan GC, Huang F, Cao Y. J. Am. Chem. Soc. 2018; 140: 8934
      CrossrefPubMed
    • 4e Liu S, Chen D, Zhou W, Yu Z, Chen L, Liu F, Chen Y. Macromolecules 2019; 52: 4359
      CrossrefPubMed
    • 4f Zhao C, Wang J, Jiao J, Huang L, Tang J. J. Mater. Chem. C 2020; 8: 28
      CrossrefPubMed
    • 4g Meng H, Li Y, Pang B, Li Y, Xiang Y, Guo L, Li X, Zhan C, Huang J. ACS Appl. Mater. Interfaces 2020; 12: 2733
      CrossrefPubMed
    • 4h Duan T, Gao J, Babics M, Kan Z, Zhong C, Singh R, Yu D, Lee J, Xiao Z, Lu S. Solar RRL 2020; 4: 1900472
      CrossrefPubMed
    • 4i Lee J, Lee SM, Chen S, Kumari T, Kang SH, Cho Y, Yang C. Adv. Mater. 2019; 31: 1804762
      CrossrefPubMed
    • 4j Genene Z, Mammo W, Wang E, Andersson MR. Adv. Mater. 2019; 31: 1807275
      CrossrefPubMed
    • 4k Jenekhe SA. Adv. Mater. 2016; 28: 124
      CrossrefPubMed
    • 4l Wang X, Han J, Huang D, Wang J, Xie Y, Liu Z, Li Y, Yang C, Zhang Y, He Z. ACS Appl. Mater. Interfaces 2020; 12: 20393
      CrossrefPubMed
    • 4m Tang A, Xiao B, Wang Y, Gao F, Tajima K, Bin H, Zhang ZG, Li Y, Wei Z, Zhou E. Adv. Funct. Mater. 2018; 28: 1704507
      CrossrefPubMed
    • 4n Xu B, Zheng Z, Zhao K, Hou J. Adv. Mater. 2016; 28: 434
      CrossrefPubMed
    • 4o Chen K, Ma R, Liu T, Luo Z, Xu X, Wang Q, Chen Y, Xiao Y, Lu X, Yan H. J. Mater. Chem. A 2020; 8: 7083
      CrossrefPubMed
    • 4p Liao Q, Sun H, Li B, Guo X. Sci. Bull. 2019; 64: 1747
      CrossrefPubMed
    • 4q Cai Y, Huo L, Sun Y. Adv. Mater. 2017; 29: 1605437
      CrossrefPubMed
    • 5a Yuan J, Xu Y, Shi G, Ling X, Ying L, Huang F, Lee TH, Woo HY, Kim JY, Cao Y. J. Mater. Chem. A 2018; 6: 10421
      CrossrefPubMed
    • 5b Yuan J, Zhang C, Chen H, Zhu C, Cheung SH, Qiu B, Cai F, Wei Q, Liu W, Yin H, Zhang R, Zhang J, Liu Y, Zhang H, Liu W, Peng H, Yang J, Meng L, Gao F, So S, Li Y, Zou Y. Sci. China Chem. 2020 . Doi: 10.1007/s11426-020-9747-9
      PubMed
  • 6 Earmme T, Hwang YJ, Subramaniyan S, Jenekhe SA. Adv. Mater. 2014; 26: 6080
    CrossrefPubMed
  • 7 Li Z, Xu X, Zhang W, Meng X, Ma W, Yartsev A, Inganaäs O, Andersson MR, Janssen RA, Wang E. J. Am. Chem. Soc. 2016; 138: 10935
    CrossrefPubMed
    • 8a Jung JW, Jo JW, Chueh CC, Liu F, Jo WH, Russell TP, Jen AK. Y. Adv. Mater. 2015; 27: 3310
      CrossrefPubMed
    • 8b Luo Z, Sun R, Zhong C, Liu T, Zhang G, Zou Y, Jiao X, Min J, Yang C. Sci. China Chem. 2020; 63: 361
      CrossrefPubMed
    • 8c Ma R, Chen Y, Liu T, Xiao Y, Luo Z, Zhang M, Luo S, Lu X, Zhang G, Li Y. J. Mater. Chem. C 2020; 8: 909
      CrossrefPubMed
    • 8d Li S, Wen X, Zhou J, Zheng N, Liu L, Xie Z. Org. Mater. 2020; 2: 071
      PubMed
    • 9a Chen D, Yao J, Chen L, Yin J, Lv R, Huang B, Liu S, Zhang ZG, Yang C, Chen Y. Angew. Chem. Int. Ed. 2018; 57: 4580
      CrossrefPubMed
    • 9b Dang D, Yu D, Wang E. Adv. Mater. 2019; 31: 1807019
      CrossrefPubMed
    • 9c Duan C, Li Z, Pang S, Zhu YL, Lin B, Colberts FJ, Leenaers PJ, Wang E, Sun ZY, Ma W. Solar RRL 2018; 2: 1800247
      CrossrefPubMed
    • 9d Kim SW, Kim H, Lee J-W, Lee C, Lim B, Lee J, Lee Y, Kim BJ. Macromolecules 2019; 52: 738
      CrossrefPubMed
  • 10 Saito M, Osaka I, Suda Y, Yoshida H, Takimiya K. Adv. Mater. 2016; 28: 6921
    CrossrefPubMed
    • 11a Wang Y, Yan Z, Uddin MA, Zhou X, Yang K, Tang Y, Liu B, Shi Y, Sun H, Deng A. Solar RRL 2019; 3: 1900107
      CrossrefPubMed
    • 11b Wang Y, Guo H, Ling S, Arrechea-Marcos I, Wang Y, López Navarrete JT, Ortiz RP, Guo X. Angew. Chem. Int. Ed. 2017; 56: 9924
      CrossrefPubMed
  • 12 Wang Y, Yan Z, Guo H, Uddin MA, Ling S, Zhou X, Su H, Dai J, Woo HY, Guo X. Angew. Chem. Int. Ed. 2017; 56: 15304
    CrossrefPubMed
  • 13 Zhang Y, Tang L, Sun H, Ling S, Yang K, Uddin MA, Guo H, Tang Y, Wang Y, Feng K. Macromol. Rapid Commun. 2019; 40: 1900394
    CrossrefPubMed
  • 14 Li Y, Tatum WK, Onorato JW, Zhang Y, Luscombe CK. Macromolecules 2018; 51: 6352
    CrossrefPubMed
  • 15 Rogers JT, Schmidt K, Toney MF, Kramer EJ, Bazan GC. Adv. Mater. 2011; 23: 2284
    CrossrefPubMed
    • 16a Guo X, Zhou N, Lou SJ, Smith J, Tice DB, Hennek JW, Ortiz RP, Navarrete JT. L, Li S, Strzalka J. Nat. Photonics 2013; 7: 825
      CrossrefPubMed
    • 16b 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
      CrossrefPubMed
    • 16c Zhou D, Liu Z, Zhu D, Yuan X, Bao X, Yang R. Org. Mater. 2019; 1: 71
      PubMed
    • 16d Cai G, Zhu J, Xiao Y, Li M, Liu K, Wang J, Wang W, Lu X, Tang Z, Lian J. J. Mater. Chem. A 2019; 7: 21432
      CrossrefPubMed
    • 17a Li G, Wang S, Li D, Liu T, Yan C, Li J, Yang W, Luo Z, Ma R, Wang X. Solar RRL 2020; 4: 1900453
      CrossrefPubMed
    • 17b Miao J, Meng B, Liu J, Wang L. Org. Mater. 2019; 1: 88
      PubMed
  • 18 Kang H, Lee W, Oh J, Kim T, Lee C, Kim BJ. Acc. Chem. Res. 2016; 49: 2424
    CrossrefPubMed
    • 19a Zhang Y.-D, Shi L.-T, Chen Y.-W. Acta Polym. Sin. 2019; 50: 13
      PubMed
    • 19b Yang C, Yuan L, Zhou R, Wang Z, Zhang J, Zhang Y, Lu K, Wei Z. Org. Mater. 2020; 2: 026
      PubMed
    • 20a Sun L, Zeng W, Xie C, Hu L, Dong X, Qin F, Wang W, Liu T, Jiang X, Jiang Y. Adv. Mater. 2020; 32: 1907840
      CrossrefPubMed
    • 20b Luo Z, Liu T, Xiao Y, Yang T, Chen Z, Zhang G, Zhong C, Ma R, Chen Y, Zou Y. Nano Energy 2019; 66: 104146
      CrossrefPubMed
    • 20c Gao W, Liu T, Sun R, Zhang G, Xiao Y, Ma R, Zhong C, Lu X, Min J, Yan H. Adv. Sci. 2020; 7: 1902657
      CrossrefPubMed
  • 21 Mihailetchi VD, Wildeman J, Blom PW. Phys. Rev. Lett. 2005; 94: 126602
    CrossrefPubMed
  • 22 Bartesaghi D, Pérez Idel C, Kniepert J, Roland S, Turbiez M, Neher D, Koster L. Nat. Commun. 2015; 6: 7083
    CrossrefPubMed
  • 23 Tumbleston JR, Collins BA, Yang L, Stuart AC, Gann E, Ma W, You W, Ade H. Nat. Photonics 2014; 8: 385
    CrossrefPubMed