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CC BY-NC-ND 4.0 · Organic Materials 2019; 01(01): 088-094
DOI: 10.1055/s-0039-3401017
DOI: 10.1055/s-0039-3401017
Original Article
Small-Molecule Donor/Polymer Acceptor Type Organic Solar Cells: Effect of Terminal Groups of Small-Molecule Donors
Funding Information The authors are grateful for the financial supports by the Natural Science Foundation of China (No. 21625403, 21875244, 21875241, 51603203, and 21761132020).Further Information
Publication History
Received: 29 September 2019
Accepted after revision: 29 October 2019
Publication Date:
27 December 2019 (online)
Abstract
Small-molecule donor/polymer acceptor type (MD/PA-type) organic solar cells (OSCs) have the great advantage of superior thermal stability. However, very few small molecular donors can match polymer acceptors, leading to low power conversion efficiency (PCE) of MD/PA-type OSCs. In this work, we studied the effect of terminal groups of small molecular donors on the optoelectronic properties and OSC device performance of MD/PA-type OSCs. We select a benzodithiophene unit bearing carbazolyl substituents as the core, terthiophene as the bridging unit, and electron-withdrawing methyl 2-cyanoacetate, 3-ethylrhodanine, and 2H-indene-1,3-dione as the terminal groups to develop three small-molecule donors. With the increase of the electron-withdrawing capability of the terminal groups, the small molecular donors exhibit redshifted absorption spectra and downshifted LUMO levels. Among the three small-molecule donors, the one with 3-ethylrhodanine terminal group exhibits the best photovoltaic performance with the PCE of 8.0% in MD/PA-type OSCs. This work provides important guidelines for the design of small-molecule donors for MD/PA-type OSC applications.
Supporting Information
Supporting information for this article is available online at: https://doi.org/10.1055/s-0039-3401017.
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References
- 1 Zhang G, Zhao J, Chow PCY, Jiang K, Zhang J, Zhu Z, Zhang J, Huang F, Yan H. Chem. Rev. 2018; 118: 3447
- 2 Collins SD, Ran NA, Heiber MC, Nguyen T-Q. Adv. Energy. Mater. 2017; 7: 1602242
- 3 Genene Z, Mammo W, Wang E, Andersson MR. Adv. Mater. 2019; 31: 1807275
- 4 Yao H, Ye L, Zhang H, Li S, Zhang S, Hou J. Chem. Rev. 2016; 116: 7397
- 5 Fan Q, Su W, Wang Y, Guo B, Jiang Y, Guo X, Liu F, Russell TP, Zhang M, Li Y. Sci. China Chem. 2018; 61: 531
- 6 Lin Y, Wang J, Zhang Z-G, Bai H, Li Y, Zhu D, Zhan X. Adv. Mater. 2015; 27: 1170
- 7 Hou J, Inganäs O, Friend RH, Gao F. Nat. Mater. 2018; 17: 119
- 8 Meng L, Zhang Y, Wan X, Li C, Zhang X, Wang Y, Ke X, Xiao Z, Ding L, Xia R, Yip H-L, Cao Y, Chen Y. Science 2018; 361: 1094
- 9 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
- 10 Fan B, Zhang D, Li M, Zhong W, Zeng Z, Ying L, Huang F, Cao Y. Sci. China Chem. 2019; 62: 746
- 11 Xu X, Feng K, Bi Z, Ma W, Zhang G, Peng Q. Adv. Mater. 2019; 31: 1901872
- 12 Ni W, Wan X, Li M, Wang Y, Chen Y. Chem. Commun. 2015; 51: 4936
- 13 Sun K, Xiao Z, Lu S, Zajaczkowski W, Pisula W, Hanssen E, White JM, Williamson RM, Subbiah J, Ouyang J, Holmes AB, Wong WWH, Jones DJ. Nat. Commun. 2015; 6: 6013
- 14 Wang J-L, Liu K-K, Yan J, Wu Z, Liu F, Xiao F, Chang Z-F, Wu HB, Cao Y, Russell TP. J. Am. Chem. Soc. 2016; 138: 7687
- 15 Huang Y, Wen W, Mukherjee S, Ade H, Kramer EJ, Bazan GC. Adv. Mater. 2014; 26: 4168
- 16 Wang J, Xiao M, Chen W, Qiu M, Du Z, Zhu W, Wen S, Wang N, Yang R. Macromolecules 2014; 47: 7823
- 17 Yao K, Chen L, Chen X, Chen Y. Chem. Mater. 2013; 25: 897
- 18 Yuan L, Zhao Y, Zhang J, Zhang Y, Zhu L, Lu K, Yan W, Wei Z. Adv. Mater. 2015; 27: 4229
- 19 Fan B, Ying L, Wang Z, He B, Jiang X-F, Huang F, Cao Y. Energy Environ. Sci. 2017; 10: 1243
- 20 Yang Y, Qiu B, Chen S, Zhou Q, Peng Y, Zhang Z-G, Yao J, Luo Z, Chen X, Xue L, Feng L, Yang C, Li Y. J. Mater. Chem. A 2018; 6: 9613
- 21 Jung JW, Russell TP, Jo WH. Chem. Mater. 2015; 27: 4865
- 22 Long X, Ding Z, Dou C, Zhang J, Liu J, Wang L. Adv. Mater. 2016; 28: 6504
- 23 Jeong M, Chen S, Lee SM, Wang Z, Yang Y, Zhang Z-G, Zhang C, Xiao M, Li Y, Yang C. Adv. Energy Mater. 2018; 8: 1702166
- 24 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
- 25 Wu H, Yue Q, Zhou Z, Chen S, Zhang D, Xu S, Zhou H, Yang C, Fan H, Zhu X. J. Mater. Chem. A 2019; 7: 15944
- 26 Bin H, Yang Y, Zhang Z-G, Ye L, Ghasemi M, Chen S, Zhang Y, Zhang C, Sun C, Xue L, Yang C, Ade H, Li Y. J. Am. Chem. Soc. 2017; 139: 5085
- 27 Feng G, Li J, He Y, Zheng W, Wang J, Li C, Tang Z, Osvet A, Li N, Brabec CJ, Yi Y, Yan H, Li W. Joule 2019; 3: 1765
- 28 Zhao R, Dou C, Liu J, Wang L. Chin. J. Polym. Sci. 2017; 35: 198
- 29 Miao J, Meng B, Liu J, Wang L. Chem. Commun. 2018; 54: 303
- 30 Wu X-F, Fu W-F, Xu Z, Shi M, Liu F, Chen H-Z, Wan J-H, Russell TP. Adv. Funct. Mater. 2015; 25: 5954
- 31 Kan B, Feng H, Yao H, Chang M, Wan X, Li C, Hou J, Chen Y. Sci. China Chem. 2018; 61: 1307
- 32 Dou C, Long X, Ding Z, Xie Z, Liu J, Wang L. Angew. Chem. Int. Ed. 2016; 55: 1436
- 33 Dou C, Ding Z, Zhang Z, Xie Z, Liu J, Wang L. Angew. Chem. Int. Ed. 2015; 127: 3719
- 34 Dou C, Liu J, Wang L. Sci. China Chem. 2017; 60: 450
- 35 Müller C. Chem. Mater. 2015; 27: 2740
- 36 Zhang Z, Ding Z, Miao J, Xin J, Ma W, Dou C, Liu J, Wang L. J. Mater. Chem. C 2019; 7: 10521
- 37 Oh S, Badgujar S, Kim DH, Lee W-E, Khan N, Jahandar M, Rasool S, Song CE, Lee HK, Shin WS, Lee J-C, Moon S-J, Lee SK. J. Mater. Chem. A 2017; 5: 15923
- 38 Kim YJ, Chung DS, Park CE. Nano. Energy 2015; 15: 343
- 39 Tang Z, Liu B, Melianas A, Bergqvist J, Trees W, Bao Q, Qian D, Inganãs O, Zhang F. Adv. Mater. 2015; 27: 1900
- 40 Geng Y, Xiao B, Izawa S, Huang J, Tajima K, Zeng Q, Zhou E. J. Mater. Chem. A 2015; 3: 22325
- 41 Yuan J, Ma W. Org. Electron. 2016; 39: 279
- 42 Zhang Z, Ding Z, Jones DJ, Wong WWH, Kan B, Bi Z, Wan X, Ma W, Chen Y, Long X, Dou C, Liu J, Wang L. Sci. China Chem. 2018; 61: 1025
- 43 Zhang Z, Ding Z, Long X, Dou C, Liu J, Wang L. J. Mater. Chem. C 2017; 5: 6812
- 44 Zhou J, Zuo Y, Wan X, Long G, Zhang Q, Ni W, Liu Y, Li Z, He G, Li C, Kan B, Li M, Chen Y. J. Am. Chem. Soc. 2013; 135: 8484
- 45 Wan J, Xu X, Zhang G, Li Y, Feng K, Peng Q. Energy Environ. Sci. 2017; 10: 1739
- 46 Cheng P, Zhao X, Zhou W, Hou J, Li Y, Zhan X. Org. Electron. 2014; 15: 2270
- 47 Li Z, Lin JDA, Phan H, Sharenko A, Proctor CM, Zalar P, Chen Z, Facchetti A, Nguyen T-Q. Adv. Funct. Mater. 2014; 24: 6989
- 48 Wang Y, Zhao X, Zhan X. J. Mater. Chem. C 2015; 3: 447
- 49 Miao J, Xu H, Meng B, Liu J, Wang L. Chin. J. Chem. 2018; 36: 411
- 50 Zhang Z, Miao J, Ding Z, Kan B, Lin B, Wan X, Ma W, Chen Y, Long X, Dou C, Zhang J, Liu J, Wang L. Nat. Commun. 2019; 10: 3271
- 51 He G, Li Z, Wan X, Liu Y, Zhou J, Long G, Zhang M, Chen Y. J. Mater. Chem. 2012; 22: 9173
- 52 Intemann JJ, Yao K, Ding F, Xu Y, Xin X, Li X, Jen AK-Y. Adv. Funct. Mater. 2015; 25: 4889
- 53 Long G, Wan X, Kan B, Liu Y, He G, Li Z, Zhang Y, Zhang Y, Zhang Q, Zhang M, Chen Y. Adv. Energy Mater. 2013; 3: 639
- 54 He G, Li Z, Wan X, Zhou J, Long G, Zhang S, Zhang M, Chen Y. J. Mater. Chem. A 2013; 1: 1801
- 55 Yuan L, Lu K, Xia B, Zhang J, Wang Z, Wang Z, Deng D, Fang J, Zhu L, Wei Z. Adv. Mater. 2016; 28: 5980