CC BY-NC-ND 4.0 · Organic Materials 2022; 4(02): 18-27
DOI: 10.1055/a-1833-8668
Organic Materials in Electronics
Original Article

Donor–Acceptor Copolymers with Rationally Regulated Side Chain Orientation for Polymer Solar Cells Processed by Non-Halogenated Solvent

Zhengwei Hu#
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
Qiri Huang#
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
Ao Song
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
Lin Shao
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
Yuanqing Bai
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
Zhicheng Hu
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
Kai Zhang
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
,
Yong Cao
a   Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 (P. R. of China)
› Author Affiliations


Abstract

A donor–acceptor (D-A) conjugated polymer PBTFO-T-1 consisting of 2,1,3-benzothiadiazole (BT) as A unit and thiophene (T) as D unit was facilely obtained by a straightforward three-step reaction. The BT unit is attached with a fluorine atom and an alkoxy chain to simultaneously endow the polymer with a deep HOMO energy level and desirable solubility. The alkoxyl chain orientation on the BT unit has been regulated and the polymer PBTFO-T-2 with regio-regularly oriented side chains was also developed to investigate the impact of the alkoxyl chain orientation on their optoelectronic properties. The PBTFO-T-1:Y6-BO polymer solar cells (PSCs) were processed with a non-halogenated solvent and achieved an optimized power conversion efficiency of 14.16%, significantly higher than 9.39% of the PBTFO-T-2:Y6-BO counterpart. It has been demonstrated that the PBTFO-T-1:Y6-BO film exhibits higher and more balanced charge transportation and superior film morphology, resulting in higher exciton generation and dissociation, less recombination and eventually the higher short-circuit current density (J sc) and fill factor. This study provides a possible strategy to develop polymer donors with low cost for future commercial applications of PSCs and gives some insights into regulating optoelectronic properties of polymer donors via rationally modifying their side chain orientation.

# Equally contributed.




Publication History

Received: 11 February 2022

Accepted after revision: 05 April 2022

Accepted Manuscript online:
25 April 2022

Article published online:
10 May 2022

© 2022. 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/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Sun Y, Liu T, Kan Y, Gao K, Tang B, Li Y. Small Sci. 2021; 1: 2100001
  • 2 Li G, Zhu R, Yang Y. Nat. Photonics 2012; 6: 153
  • 3 Song S, Lee KT, Koh CW, Shin H, Gao M, Woo HY, Vak D, Kim JY. Energy Environ. Sci. 2018; 11: 3248
  • 4 Li Y, Huang X, Ding K, Sheriff Jr HKM, Ye L, Liu H, Li CZ, Ade H, Forrest SR. Nat. Commun. 2021; 12: 5419
  • 5 Qin L, Liu X, Zhang X, Yu J, Yang L, Zhao F, Huang M, Wang K, Wu X, Li Y, Chen H, Wang K, Xia J, Lu X, Gao F, Yi Y, Huang H. Angew. Chem. Int. Ed. 2020; 59: 15043
  • 6 Xu Y, Yao H, Hou J. Chin. J. Chem. 2019; 37: 207
  • 7 Tang CW. Appl. Phys. Lett. 1986; 48: 183
  • 8 Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ. Science 1995; 270: 1789
  • 9 Søndergaard R, Hösel M, Angmo D, Larsen-Olsen TT, Krebs FC. Mater. Today 2012; 15: 36
  • 10 Fan B, Zhang D, Li M, Zhong W, Zeng Z, Ying L, Huang F, Cao Y. Sci. China Chem. 2019; 62: 746
  • 11 Cui Y, Yao H, Hong L, Zhang T, Xu Y, Xian K, Gao B, Qin J, Zhang J, Wei Z, Hou J. Adv. Mater. 2019; 31: 1808356
  • 12 Liu Q, Jiang Y, Jin K, Qin J, Xu J, Li W, Xiong J, Liu J, Xiao Z, Sun K, Yang S, Zhang X, Ding L. Sci. Bull. 2020; 65: 272
  • 13 Cui Y, Yao H, Hong L, Zhang T, Tang Y, Lin B, Xian K, Gao B, An C, Bi P, Ma W, Hou J. Natl. Sci. Rev. 2020; 7: 1239
  • 14 Huang F, Cao Y. Acta Polym. Sin. 2016; 4: 399
  • 15 Chen S, Feng L, Jia T, Jing J, Hu Z, Zhang K, Huang F. Sci. China Chem. 2021; 64: 1192
  • 16 Dai S, Zhan X. Acta Polym. Sin. 2017; 11: 1706
  • 17 Yuan J, Zhang Y, Zhou L, Zhang G, Yip H-L, Lau T-K, Lu X, Zhu C, Peng H, Johnson PA, Leclerc M, Cao Y, Ulanski J, Li Y, Zou Y. Joule 2019; 3: 1140
  • 18 Luo Z, Liu T, Wang Y, Zhang G, Sun R, Chen Z, Zhong C, Wu J, Chen Y, Zhang M, Zou Y, Ma W, Yan H, Min J, Li Y, Yang C. Adv. Energy Mater. 2019; 9: 1900041
  • 19 Gao K, Kan Y, Chen X, Liu F, Kan B, Nian L, Wan X, Chen Y, Peng X, Russell TP, Cao Y, Jen AK. Adv. Mater. 2020; 32: 1906129
  • 20 Zhang Y, Cai G, Li Y, Zhang Z, Li T, Zuo X, Lu X, Lin Y. Adv. Mater. 2021; 33: 2008134
  • 21 Zhu X, Liu S, Yue Q, Liu W, Sun S, Xu S. CCS Chem. 2021; 3: 1070
  • 22 Lin Y, Zhao F, He Q, Huo L, Wu Y, Parker TC, Ma W, Sun Y, Wang C, Zhu D, Heeger AJ, Marder SR, Zhan X. J. Am. Chem. Soc. 2016; 138: 4955
  • 23 Ma S, Feng H, Liu X, Hu Z, Yang X, Liang Y, Zhang J, Huang F, Cao Y. ChemSusChem 2021; 14: 3544
  • 24 Zhang Y, Wang Y, Xie Z, Shan T, Zhu L, Liu F, Zhong H. J. Mater. Chem. C 2020; 8: 17229
  • 25 Cui C, Li Y. Energy Environ. Sci. 2019; 12: 3225
  • 26 Zhang M, Zhu L, Zhou G, Hao T, Qiu C, Zhao Z, Hu Q, Larson BW, Zhu H, Ma Z, Tang Z, Feng W, Zhang Y, Russell TP, Liu F. Nat. Commun. 2021; 12: 309
  • 27 Li S, Ye L, Zhao W, Yan H, Yang B, Liu D, Li W, Ade H, Hou J. J. Am. Chem. Soc. 2018; 140: 7159
  • 28 Yao H, Cui Y, Qian D, Ponseca Jr CS, Honarfar A, Xu Y, Xin J, Chen Z, Hong L, Gao B, Yu R, Zu Y, Ma W, Chabera P, Pullerits T, Yartsev A, Gao F, Hou J. J. Am. Chem. Soc. 2019; 141: 7743
  • 29 Zhao W, Qian D, Zhang S, Li S, Inganas O, Gao F, Hou J. Adv. Mater. 2016; 28: 4734
  • 30 Ren J, Bi P, Zhang J, Liu J, Wang J, Xu Y, Wei Z, Zhang S, Hou J. Natl. Sci. Rev. 2021; 8: nwab031
  • 31 Bin H, Gao L, Zhang ZG, Yang Y, Zhang Y, Zhang C, Chen S, Xue L, Yang C, Xiao M, Li Y. Nat. Commun. 2016; 7: 13651
  • 32 Lan L, Chen Z, Hu Q, Ying L, Zhu R, Liu F, Russell TP, Huang F, Cao Y. Adv. Sci. 2016; 3: 1600032
  • 33 Zheng Z, Hu Q, Zhang S, Zhang D, Wang J, Xie S, Wang R, Qin Y, Li W, Hong L, Liang N, Liu F, Zhang Y, Wei Z, Tang Z, Russell TP, Hou J, Zhou H. Adv. Mater. 2018; 30: 1801801
  • 34 Osedach TP, Andrew TL, Bulović V. Energy Environ. Sci. 2013; 6: 711
  • 35 Yuan D, Pan F, Zhang L, Jiang H, Chen M, Tang W, Qin G, Cao Y, Chen J. Sol. RRL 2020; 4: 2000062
  • 36 Wang Q, Li M, Zhang X, Qin Y, Wang J, Zhang J, Hou J, Janssen RAJ, Geng Y. Macromolecules 2019; 52: 4464
  • 37 Brabec CJ, Distler A, Du X, Egelhaaf HJ, Hauch J, Heumueller T, Li N. Adv. Energy Mater. 2020; 10: 2001864
  • 38 Pang S, Wang Z, Yuan X, Pan L, Deng W, Tang H, Wu H, Chen S, Duan C, Huang F, Cao Y. Angew. Chem. Int. Ed. 2021; 60: 8813
  • 39 Baran D, Ashraf RS, Hanifi DA, Abdelsamie M, Gasparini N, Rohr JA, Holliday S, Wadsworth A, Lockett S, Neophytou M, Emmott CJ, Nelson J, Brabec CJ, Amassian A, Salleo A, Kirchartz T, Durrant JR, McCulloch I. Nat. Mater. 2017; 16: 363
  • 40 Xiao J, Jia X, Duan C, Huang F, Yip HL, Cao Y. Adv. Mater. 2021; 33: 2008158
  • 41 Yang C, Zhang S, Ren J, Gao M, Bi P, Ye L, Hou J. Energy Environ. Sci. 2020; 13: 2864
  • 42 Liu F, Zhang J, Zhou Z, Zhang J, Wei Z, Zhu X. J. Mater. Chem. A 2017; 5: 16573
  • 43 Sun C, Pan F, Bin H, Zhang J, Xue L, Qiu B, Wei Z, Zhang Z-G, Li Y. Nat. Commun. 2018; 9: 743
  • 44 Wang H, Lu H, Chen YN, Ran G, Zhang A, Li D, Yu N, Zhang Z, Liu Y, Xu X, Zhang W, Bao Q, Tang Z, Bo Z. Adv. Mater. 2021; 34: 2105483
  • 45 Zhang B, Yu Y, Zhou J, Wang Z, Tang H, Xie S, Xie Z, Hu L, Yip HL, Ye L, Ade H, Liu Z, He Z, Duan C, Huang F, Cao Y. Adv. Energy Mater. 2020; 10: 1904247
  • 46 Che X, Li Y, Qu Y, Forrest SR. Nat. Energy 2018; 3: 422
  • 47 Chen Y, Cui Y, Zhang S, Hou J. Polym. Chem. 2015; 6: 4089
  • 48 Chen X, Liu X, Burgers MA, Huang Y, Bazan GC. Angew. Chem. Int. Ed. 2014; 53: 14378
  • 49 Mei J, Bao Z. Chem. Mater. 2013; 26: 604
  • 50 Burgués-Ceballos I, Machui F, Min J, Ameri T, Voigt MM, Luponosov YN, Ponomarenko SA, Lacharmoise PD, Campoy-Quiles M, Brabec CJ. Adv. Funct. Mater. 2014; 24: 1449
  • 51 McDowell C, Bazan GC. Curr. Opin. Green Sustainable Chem. 2017; 5: 49
  • 52 Chen SH, Liao CH, Chang CY, Huang KM, Chen JY, Chen CH, Meng HF, Zan HW, Horng SF, Lin YC, Yeh MH. Org. Electron. 2019; 75: 105376
  • 53 Zhang Q, Kelly MA, Bauer N, You W. Acc. Chem. Res. 2017; 50: 2401
  • 54 Hong L, Yao H, Wu Z, Cui Y, Zhang T, Xu Y, Yu R, Liao Q, Gao B, Xian K, Woo HY, Ge Z, Hou J. Adv. Mater. 2019; 31: 1903441
  • 55 He D, Zhao F, Wang C, Lin Y. Adv. Funct. Mater. 2022; 2111855
  • 56 Mihailetchi VD, Koster LJ, Hummelen JC, Blom PW. Phys. Rev. Lett. 2004; 93: 216601
  • 57 Zhang X, Jiang D-W, Yang G-L, Zhu Y-C, Tian J, Cao H-L, Gao Y, Zhang W-A. Chin. J. Polym. Sci. 2021; 39: 692
  • 58 Tang H, Chen H, Yan C, Huang J, Fong PWK, Lv J, Hu D, Singh R, Kumar M, Xiao Z, Kan Z, Lu S, Li G. Adv. Energy Mater. 2020; 10: 2001076
  • 59 Mihailetchi VD, Wildeman J, Blom PW. Phys. Rev. Lett. 2005; 94: 126602
  • 60 Koster LJA, Mihailetchi VD, Xie H, Blom PWM. Appl. Phys. Lett. 2005; 87: 203502
  • 61 Wetzelaer GAH, Kuik M, Lenes M, Blom PWM. Appl. Phys. Lett. 2011; 99: 153506