Abstract
A series of novel wide bandgap small molecules (IFT-ECA, IFT-M, IFT-TH and IFT-IC) based on the A-D-A structure with indenofluorene core, thiophene bridge, and different electron-deficient end-capping groups, were synthesized and used as non-fullerene acceptors in organic solar cells. The influences of end-capping groups on the device performance were studied. The four materials exhibited different physical and chemical properties due to the variation of end-capping groups, which further affect the exciton dissociation, charge transport, morphology of the bulk-heterojunction films and device performance. Among them, IFT-IC-based device delivered the best power conversion efficiency of 7.16% due to proper nano-scale phase separation morphology and high electron mobility, while the devices based on the other acceptors achieved lower device performance (4.14% for IFT-TH, <1% for IFT-ECA and IFT-M). Our results indicate the importance of choosing suitable electron-withdrawing groups to construct high-performance non-fullerene acceptors based on A-D-A motif.
Similar content being viewed by others
References
Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ. Science, 1995, 270: 1789–1791
Thompson BC, Fréchet JMJ. Angew Chem Int Ed, 2008, 47: 58–77
Andersen TR, Dam HF, Hösel M, Helgesen M, Carlé JE, Larsen-Olsen TT, Gevorgyan SA, Andreasen JW, Adams J, Li N, Machui F, Spyropoulos GD, Ameri T, Lemaître N, Legros M, Scheel A, Gaiser D, Kreul K, Berny S, Lozman OR, Nordman S, Välimäki M, Vilkman M, Søndergaard RR, Jørgensen M, Brabec CJ, Krebs FC. Energy Environ Sci, 2014, 7: 2925–2933
Lu L, Zheng T, Wu Q, Schneider AM, Zhao D, Yu L. Chem Rev, 2015, 115: 12666–12731
Wang M, Hu X, Liu P, Li W, Gong X, Huang F, Cao Y. J Am Chem Soc, 2011, 133: 9638–9641
Duan C, Huang F, Cao Y. J Mater Chem, 2012, 22: 10416–10434
Liu Y, Zhao J, Li Z, Mu C, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H. Nat Commun, 2014, 5: 5293
He Z, Xiao B, Liu F, Wu H, Yang Y, Xiao S, Wang C, Russell TP, Cao Y. Nat Photon, 2015, 9: 174–179
Kan B, Li M, Zhang Q, Liu F, Wan X, Wang Y, Ni W, Long G, Yang X, Feng H, Zuo Y, Zhang M, Huang F, Cao Y, Russell TP, Chen Y. J Am Chem Soc, 2015, 137: 3886–3893
Jin Y, Chen Z, Dong S, Zheng N, Ying L, Jiang XF, Liu F, Huang F, Cao Y. Adv Mater, 2016, 28: 9811–9818
Lin Y, Zhan X. Acc Chem Res, 2016, 49: 175–183
Yao H, Ye L, Zhang H, Li S, Zhang S, Hou J. Chem Rev, 2016, 116: 7397–7457
Zhan X, Tan Z, Domercq B, An Z, Zhang X, Barlow S, Li Y, Zhu D, Kippelen B, Marder SR. J Am Chem Soc, 2007, 129: 7246–7247
Zhan X, Facchetti A, Barlow S, Marks TJ, Ratner MA, Wasielewski MR, Marder SR. Adv Mater, 2011, 23: 268–284
Lin Y, Zhan X. Adv Energy Mater, 2015, 5: 1501063
Nielsen CB, Holliday S, Chen HY, Cryer SJ, McCulloch I. Acc Chem Res, 2015, 48: 2803–2812
Chen W, Zhang Q. J Mater Chem C, 2017, 5: 1275–1302
Duan C, Zango G, García Iglesias M, Colberts FJM, Wienk MM, Martínez-Díaz MV, Janssen RAJ, Torres T. Angew Chem Int Ed, 2017, 56: 148–152
Zhou E, Cong J, Wei Q, Tajima K, Yang C, Hashimoto K. Angew Chem Int Ed, 2011, 50: 2799–2803
Zhou E, Cong J, Hashimoto K, Tajima K. Adv Mater, 2013, 25: 6991–6996
Jung JW, Jo JW, Chueh CC, Liu F, Jo WH, Russell TP, Jen AKY. Adv Mater, 2015, 27: 3310–3317
Gao L, Zhang ZG, Xue L, Min J, Zhang J, Wei Z, Li Y. Adv Mater, 2016, 28: 1884–1890
Xue L, Yang Y, Zhang ZG, Dong X, Gao L, Bin H, Zhang J, Yang YX, Li Y. J Mater Chem A, 2016, 4: 5810–5816
Xue L, Yang Y, Zhang ZG, Zhang J, Gao L, Bin H, Yang YX, Li Y. Chem Asian J, 2016, 11: 2785–2791
Zhou E, Nakano M, Izawa S, Cong J, Osaka I, Takimiya K, Tajima K. ACS Macro Lett, 2014, 3: 872–875
Yang J, Xiao B, Tajima K, Nakano M, Takimiya K, Tang A, Zhou E. Macromolecules, 2017, 50: 3179–3185
Liu S, Kan Z, Thomas S, Cruciani F, Brédas JL, Beaujuge PM. Angew Chem Int Ed, 2016, 55: 12996–13000
Long X, Ding Z, Dou C, Zhang J, Liu J, Wang L. Adv Mater, 2016, 28: 6504–6508
Yan Q, Zhou Y, Zheng YQ, Pei J, Zhao D. Chem Sci, 2013, 4: 4389–4394
Zhang X, Lu Z, Ye L, Zhan C, Hou J, Zhang S, Jiang B, Zhao Y, Huang J, Zhang S, Liu Y, Shi Q, Liu Y, Yao J. Adv Mater, 2013, 25: 5791–5797
Lin Y, Wang Y, Wang J, Hou J, Li Y, Zhu D, Zhan X. Adv Mater, 2014, 26: 5137–5142
Lu Z, Jiang B, Zhang X, Tang A, Chen L, Zhan C, Yao J. Chem Mater, 2014, 26: 2907–2914
Zang Y, Li CZ, Chueh CC, Williams ST, Jiang W, Wang ZH, Yu JS, Jen AKY. Adv Mater, 2014, 26: 5708–5714
Sun D, Meng D, Cai Y, Fan B, Li Y, Jiang W, Huo L, Sun Y, Wang Z. J Am Chem Soc, 2015, 137: 11156–11162
Zhao J, Li Y, Lin H, Liu Y, Jiang K, Mu C, Ma T, Lin Lai JY, Hu H, Yu D, Yan H. Energy Environ Sci, 2015, 8: 520–525
Lan L, Chen Z, Ying L, Huang F, Cao Y. Org Electron, 2016, 30: 176–181
Li S, Liu W, Li CZ, Lau TK, Lu X, Shi M, Chen H. J Mater Chem A, 2016, 4: 14983–14987
Liu Z, Wu Y, Zhang Q, Gao X. J Mater Chem A, 2016, 4: 17604–17622
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: 10184–10190
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: 375–380
Wu Q, Zhao D, Schneider AM, Chen W, Yu L. J Am Chem Soc, 2016, 138: 7248–7251
Zhang X, Yao J, Zhan C. Sci China Chem, 2016, 59: 209–217
Zhong H, Wu CH, Li CZ, Carpenter J, Chueh CC, Chen JY, Ade H, Jen AKY. Adv Mater, 2016, 28: 951–958
Liu X, Liu T, Duan C, Wang J, Pang S, Xiong W, Sun Y, Huang F, Cao Y. J Mater Chem A, 2017, 5: 1713–1723
Zhang A, Li C, Yang F, Zhang J, Wang Z, Wei Z, Li W. Angew Chem Int Ed, 2017, 56: 2694–2698
Lin Y, Zhan X. Mater Horiz, 2014, 1: 470–488
Holliday S, Ashraf RS, Nielsen CB, Kirkus M, Röhr JA, Tan CH, Collado-Fregoso E, Knall AC, Durrant JR, Nelson J, McCulloch I. J Am Chem Soc, 2015, 137: 898–904
Lin Y, Wang J, Zhang ZG, Bai H, Li Y, Zhu D, Zhan X. Adv Mater, 2015, 27: 1170–1174
Lin Y, Zhang ZG, Bai H, Wang J, Yao Y, Li Y, Zhu D, Zhan X. Energy Environ Sci, 2015, 8: 610–616
Wu Y, Bai H, Wang Z, Cheng P, Zhu S, Wang Y, Ma W, Zhan X. Energy Environ Sci, 2015, 8: 3215–3221
Bin H, Zhang ZG, Gao L, Chen S, Zhong L, Xue L, Yang C, Li Y. J Am Chem Soc, 2016, 138: 4657–4664
Holliday S, Ashraf RS, Wadsworth A, Baran D, Yousaf SA, Nielsen CB, Tan CH, Dimitrov SD, Shang Z, Gasparini N, Alamoudi M, Laquai F, Brabec CJ, Salleo A, Durrant JR, Mc Culloch I. Nat Commun, 2016, 7: 11585
Li S, Ye L, Zhao W, Zhang S, Mukherjee S, Ade H, Hou J. Adv Mater, 2016, 28: 9423–9429
Li Y, Qian D, Zhong L, Lin JD, Jiang ZQ, Zhang ZG, Zhang Z, Li Y, Liao LS, Zhang F. Nano Energy, 2016, 27: 430–438
Lin Y, He Q, Zhao F, Huo L, Mai J, Lu X, Su CJ, Li T, Wang J, Zhu J, Sun Y, Wang C, Zhan X. J Am Chem Soc, 2016, 138: 2973–2976
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: 4955–4961
Yang Y, Zhang ZG, Bin H, Chen S, Gao L, Xue L, Yang C, Li Y. J Am Chem Soc, 2016, 138: 15011–15018
Yao H, Chen Y, Qin Y, Yu R, Cui Y, Yang B, Li S, Zhang K, Hou J. Adv Mater, 2016, 28: 8283–8287
Zhao W, Qian D, Zhang S, Li S, Inganäs O, Gao F, Hou J. Adv Mater, 2016, 28: 4734–4739
Jia B, Wu Y, Zhao F, Yan C, Zhu S, Cheng P, Mai J, Lau TK, Lu X, Su CJ, Wang C, Zhan X. Sci China Chem, 2017, 60: 257–263
Zhao J, Li Y, Yang G, Jiang K, Lin H, Ade H, Ma W, Yan H. Nat Energy, 2016, 1: 15027
Lin Y, Zhao F, Wu Y, Chen K, Xia Y, Li G, Prasad SKK, Zhu J, Huo L, Bin H, Zhang ZG, Guo X, Zhang M, Sun Y, Gao F, Wei Z, Ma W, Wang C, Hodgkiss J, Bo Z, Inganäs O, Li Y, Zhan X. Adv Mater, 2017, 29: 1604155
Li M, Liu Y, Ni W, Liu F, Feng H, Zhang Y, Liu T, Zhang H, Wan X, Kan B, Zhang Q, Russell TP, Chen Y. J Mater Chem A, 2016, 4: 10409–10413
Ni W, Li M, Kan B, Liu F, Wan X, Zhang Q, Zhang H, Russell TP, Chen Y. Chem Commun, 2016, 52: 465–468
Wang K, Firdaus Y, Babics M, Cruciani F, Saleem Q, El Labban A, Alamoudi MA, Marszalek T, Pisula W, Laquai F, Beaujuge PM. Chem Mater, 2016, 28: 2200–2208
Zhang J, Zhao B, Mi Y, Liu H, Guo Z, Bie G, Wei W, Gao C, An Z. Dyes Pig, 2017, 140: 261–268
Zheng Q, Jung BJ, Sun J, Katz HE. J Am Chem Soc, 2010, 132: 5394–5404
Cheng YJ, Hung LC, Cao FY, Kao WS, Chang CY, Hsu CS. J Polym Sci A Polym Chem, 2011, 49: 1791–1801
Leriche P, Frère P, Cravino A, Alévêque O, Roncali J. J Org Chem, 2007, 72: 8332–8336
Scharber MC, Mühlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CJ. Adv Mater, 2006, 18: 789–794
Acknowledgments
This work was supported by the Ministry of Science and Technology (2014CB643501), the National Natural Science Foundation of China (21520102006, 21634004, 21490573), and the Guangdong Natural Science Foundation (S2012030006232).
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Jia, J., Zheng, N., Wang, Z. et al. The effect of end-capping groups in A-D-A type non-fullerene acceptors on device performance of organic solar cells. Sci. China Chem. 60, 1458–1467 (2017). https://doi.org/10.1007/s11426-017-9102-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-017-9102-1