Effect of Extended π-Conjugation of Central Cores on Photovoltaic Properties of Asymmetric Wide-Bandgap Nonfullerene Acceptors

Tian Xia; Chao Li; Hwa Sook Ryu; Xiaobo Sun; Han Young Woo; Yanming Sun

doi:10.1055/s-0040-1709999

CC BY-NC-ND 4.0 · Organic Materials 2020; 02(02): 173-181
DOI: 10.1055/s-0040-1709999

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).

Effect of Extended π-Conjugation of Central Cores on Photovoltaic Properties of Asymmetric Wide-Bandgap Nonfullerene Acceptors

Tian Xia

^aSchool of Chemistry, Beihang University, Beijing 100191,China

,

Chao Li

^aSchool of Chemistry, Beihang University, Beijing 100191,China

,

Hwa Sook Ryu

^bDepartment of Chemistry, College of Science, Korea University, Seoul 136–713, Republic of Korea

,

Xiaobo Sun

^aSchool of Chemistry, Beihang University, Beijing 100191,China

,

Han Young Woo

^bDepartment of Chemistry, College of Science, Korea University, Seoul 136–713, Republic of Korea

,

Yanming Sun

^aSchool of Chemistry, Beihang University, Beijing 100191,China

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Abstract

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Abstract

Tremendous efforts have been dedicated to develop low-bandgap nonfullerene acceptors (NFAs) for organic solar cells (OSCs). In comparison, the NFAs with a wide bandgap (WBG) have received less attention. Here, three novel acceptor–donor–acceptor type WBG NFAs (TPT-T, TPTT-T, and TPTTT-T) have been designed and synthesized with different fused central cores by varying the π-conjugation length and molecular structures, which all exhibit wide optical bandgaps over 1.8 eV. The successive π-conjugation extension of electron-donating central cores (from TPT-T to TPTT-T and to TPTTT-T) induces red-shifted absorption spectra, lower optical bandgap, and enhanced electron mobility simultaneously. As a result, the optimized OSC devices based on TPTTT-T:PBT1-C achieved a power conversion efficiency of 7.42%, which was higher than those of PBT1-C:TPTT-T (6.93%) and PBT1-C:TPT-T (6.11%) based devices. These results indicate that extending the molecular π-conjugation structure is an effective strategy to design efficient NFAs for OSCs.

Key words

organic solar cells - nonfullerene acceptors - π-conjugation - wide-bandgap - power conversion efficiency

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References

References
1 Li G, Zhu R, Yang Y. Nat. Photonics 2012; 6: 153
2 Heeger AJ. Adv. Mater. 2014; 26: 10
3 Cai Y, Huo L, Sun Y. Adv. Mater. 2017; 29: 1605437
4 Fu H, Wang Z, Sun Y. Solar RRL 2018; 2: 1700158
5 Xie Y, Huo L, Fan B, Fu H, Cai Y, Zhang L, Li Z, Wang Y, Ma W, Chen Y, Sun Y. Adv. Funct. Mater. 2018; 28: 1800627
6 Fu H, Wang Z, Sun Y. Angew. Chem. Int. Ed. 2019; 58: 4442
7 Xia T, Cai Y, Fu H, Sun Y. Sci. China Chem. 2019; 62: 662
8 Günes S, Neugebauer H, Sariciftci NS. Chem. Rev. 2007; 107: 1324
9 Huo L, Liu T, Sun X, Cai Y, Heeger AJ, Sun Y. Adv. Mater. 2015; 27: 2938
10 Huo L, Liu T, Fan B, Zhao Z, Sun X, Wei D, Yu M, Liu Y, Sun Y. Adv. Mater. 2015; 27: 6969
11 Yao H, Ye L, Zhang H, Li S, Zhang S, Hou J. Chem. Rev. 2016; 116: 7397
12 Xie Y, Yang F, Li Y, Uddin MA, Bi P, Fan B, Cai Y, Hao X, Woo HY, Li W, Liu F, Sun Y. Adv. Mater. 2018; 30: 1803045
13 Liu T, Troisi A. Adv. Mater. 2013; 25: 1038
14 Yan C, Barlow S, Wang Z, Yan H, Jen AK. Y, Marder SR, Zhan X. Nat. Rev. Mater. 2018; 3: 18003
15 Lin Y, Zhan X. Mater. Horiz. 2014; 1: 470
16 Cheng P, Li G, Zhan X, Yang Y. Nat. Photonics 2018; 12: 131
17 Lin Y, Wang J, Zhang Z-G, Bai H, Li Y, Zhu D, Zhan X. Adv. Mater. 2015; 27: 1170
18 Lin Y, He Q, Zhao F, Huo L, Mai J, Lu X, Su C-J, Li T, Wang J, Zhu J, Sun Y, Wang C, Zhan X. J. Am. Chem. Soc. 2016; 138: 2973
19 Sun D, Meng D, Cai Y, Fan B, Li Y, Jiang W, Huo L, Sun Y, Wang Z. J. Am. Chem. Soc. 2015; 137: 11156
20 Meng D, Sun D, Zhong C, Liu T, Fan B, Huo L, Li Y, Jiang W, Choi H, Kim T, Kim JY, Sun Y, Wang Z, Heeger AJ. J. Am. Chem. Soc. 2016; 138: 375
21 Meng D, Fu H, Xiao C, Meng X, Winands T, Ma W, Wei W, Fan B, Huo L, Doltsinis NL, Li Y, Sun Y, Wang Z. J. Am. Chem. Soc. 2016; 138: 10184
22 Liang N, Zhu X, Zheng Z, Meng D, Liu G, Zhang J, Li S, Li Y, Hou J, Hu B, Wang Z. Chem. Mater. 2019; 31: 3636
23 Lin H, Chen S, Li Z, Lai JY. L, Yang G, McAfee T, Jiang K, Li Y, Liu Y, Hu H, Zhao J, Ma W, Ade H, Yan H. Adv. Mater. 2015; 27: 7299
24 Li S, Ye L, Zhao W, Zhang S, Mukherjee S, Ade H, Hou J. Adv. Mater. 2016; 28: 9423
25 Zhao W, Li S, Yao H, Zhang S, Zhang Y, Yang B, Hou J. J. Am. Chem. Soc. 2017; 139: 7148
26 Yao H, Chen Y, Qin Y, Yu R, Cui Y, Yang B, Li S, Zhang K, Hou J. Adv. Mater. 2016; 28: 8283
27 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
28 Zhang H, Yao H, Hou J, Zhu J, Zhang J, Li W, Yu R, Gao B, Zhang S, Hou J. Adv. Mater. 2018; 30: 1800613
29 Xie D, Liu T, Gao W, Zhong C, Huo L, Luo Z, Wu K, Xiong W, Liu F, Sun Y, Yang C. Solar RRL 2017; 1: 1700044
30 Li C, Xie Y, Fan B, Han G, Yi Y, Sun Y. J. Mater. Chem. C 2018; 6: 4873
31 Song J, Li C, Ye L, Koh C, Cai Y, Wei D, Woo HY, Sun Y. J. Mater. Chem. A 2018; 6: 18847
32 Li C, Song J, Ye L, Koh C, Weng K, Fu H, Cai Y, Xie Y, Wei D, Woo HY, Sun Y. Solar RRL 2019; 3: 1800246
33 Li C, Song J, Cai Y, Han G, Zheng W, Yi Y, Ryu HS, Woo HY, Sun Y. J. Energy Chem. 2020; 40: 144
34 Li C, Xia T, Song J, Fu H, Ryu HS, Weng K, Ye L, Woo HY, Sun Y. J. Mater. Chem. A 2019; 7: 1435
35 Ye L, Xie Y, Xiao Y, Song J, Li C, Fu H, Weng K, Lu X, Tan S, Sun Y. J. Mater. Chem. A 2019; 7: 8055
36 Xie R, Ying L, Liao H, Chen Z, Huang F, Cao Y. Front. Chem. 2018; 6: 303
37 Wang J-L, Liu K-K, Hong L, Ge G-Y, Zhang C, Hou J. ACS Energy Lett. 2018; 3: 2967
38 Chang S-L, Cao F-Y, Huang W-C, Huang P-K, Huang K-H, Hsu C-S, Cheng Y-J. ACS Energy Lett. 2018; 3: 1722
39 Liu Y, Zuo L, Shi X, Jen AK. Y, Ginger DS. ACS Energy Lett. 2018; 3: 2396
40 Li Y, Lin J-D, Che X, Qu Y, Liu F, Liao L-S, Forrest SR. J. Am. Chem. Soc. 2017; 139: 17114
41 Zhang G, Zhao J, Chow PC. Y, Jiang K, Zhang J, Zhu Z, Zhang J, Huang F, Yan H. Chem. Rev. 2018; 118: 3447
42 Zhai W, Tang A, Xiao B, Wang X, Chen F, Zhou E. Sci. Bull. 2018; 63: 845
43 Huang C, Liao X, Gao K, Zuo L, Lin F, Shi X, Li C-Z, Liu H, Li X, Liu F, Chen Y, Chen H, Jen AK. Y. Chem. Mater. 2018; 30: 5429
44 Shi X, Zuo L, Jo SB, Gao K, Lin F, Liu F, Jen AK. Y. Chem. Mater. 2017; 29: 8369
45 Shi X, Liao X, Gao K, Zuo L, Chen J, Zhao J, Liu F, Chen Y, Jen AK. Y. Adv. Funct. Mater. 2018; 28: 1802324
46 Sun J, Ma X, Zhang Z, Yu J, Zhou J, Yin X, Yang L, Geng R, Zhu R, Zhang F, Tang W. Adv. Mater. 2018; 30: 1707150
47 Wang J, Wang W, Wang X, Wu Y, Zhang Q, Yan C, Ma W, You W, Zhan X. Adv. Mater. 2017; 29: 1702125
48 Zhao F, Dai S, Wu Y, Zhang Q, Wang J, Jiang L, Ling Q, Wei Z, Ma W, You W, Wang C, Zhan X. Adv. Mater. 2017; 29: 1700144
49 Li Y, Zhong L, Gautam B, Bin H-J, Lin J-D, Wu F-P, Zhang Z, Jiang Z-Q, Zhang Z-G, Gundogdu K, Li Y, Liao L-S. Energy Environ. Sci. 2017; 10: 1610
50 Li W, Ye L, Li S, Yao H, Ade H, Hou J. Adv. Mater. 2018; 30: 1707170
51 Kan B, Zhang J, Liu F, Wan X, Li C, Ke X, Wang Y, Feng H, Zhang Y, Long G, Friend RH, Bakulin AA, Chen Y. Adv. Mater. 2018; 30: 1704904
52 Zhang Y, Kan B, Sun Y, Wang Y, Xia R, Ke X, Yi Y-Q-Q, Li C, Yip H-L, Wan X, Cao Y, Chen Y. Adv. Mater. 2018; 30: 1707508
53 Zuo L, Yu J, Shi X, Lin F, Tang W, Jen AK. Y. Adv. Mater. 2017; 29: 1702547
54 Shi X, Chen J, Gao K, Zuo L, Yao Z, Liu F, Tang J, Jen AK. Y. Adv. Energy Mater. 2018; 8: 1702831
55 Zuo L, Shi X, Jo SB, Liu Y, Lin F, Jen AK. Y. Adv. Mater. 2018; 30: 1706816
56 Yao H, Cui Y, Yu R, Gao B, Zhang H, Hou J. Angew. Chem. Int. Ed. 2017; 56: 3045
57 He B, Yang B, Kolaczkowski MA, Anderson CA, Klivansky LM, Chen TL, Brady MA, Liu Y. ACS Energy Lett. 2018; 3: 1028
58 Gong Y, Kan Z, Xu W, Wang Y, AlShammari SH, Laquai F, Lai W-Y, Huang W. Solar RRL 2018; 2: 1800120
59 Xiao B, Tang A, Zhang J, Mahmood A, Wei Z, Zhou E. Adv Energy Mater. 2017; 7: 1602269
60 Tang A, Xiao B, Wang Y, Gao F, Tajima K, Bin H, Zhang Z-G, Li Y, Wei Z, Zhou E. Adv. Funct. Mater. 2018; 28: 1704507
61 Tang A, Xiao B, Chen F, Zhang J, Wei Z, Zhou E. Adv. Energy Mater. 2018; 8: 1801582
62 Tang A, Song W, Xiao B, Guo J, Min J, Ge Z, Zhang J, Wei Z, Zhou E. Chem. Mater. 2019; 31: 3941
63 Jia J, Zheng N, Wang Z, Huang Y, Duan C, Huang F, Cao Y. Sci. China Chem. 2017; 60: 1458
64 Wang P, Fan H, Zhang C, Zhu X. Mater. Chem. Front. 2018; 2: 136
65 Li C, Fu H, Xia T, Sun Y. Adv. Energy Mater. 2019; 9: 1900999
66 Ko EY, Park GE, Lee JH, Kim HJ, Lee DH, Ahn H, Uddin MA, Woo HY, Cho MJ, Choi DH. ACS Appl. Mater. Interfaces 2017; 9: 8838
67 Liu T, Huo L, Chandrabose S, Chen K, Han G, Qi F, Meng X, Xie D, Ma W, Yi Y, Hodgkiss JM, Liu F, Wang J, Yang C, Sun Y. Adv. Mater. 2018; 30: 1707353
68 Faist MA, Shoaee S, Tuladhar S, Dibb GF. A, Foster S, Gong W, Kirchartz T, Bradley DD. C, Durrant JR, Nelson J. Adv. Energy Mater. 2013; 3: 744
69 Riedel I, Parisi J, Dyakonov V, Lutsen L, Vanderzande D, Hummelen JC. Adv. Funct. Mater. 2004; 14: 38

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