CC BY-NC-ND 4.0 · Organic Materials 2019; 01(01): 088-094
DOI: 10.1055/s-0039-3401017
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/). (2019) The Author(s).

Small-Molecule Donor/Polymer Acceptor Type Organic Solar Cells: Effect of Terminal Groups of Small-Molecule Donors

Junhui Miao
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, People's Republic of China
b   University of Science and Technology of China, Hefei, People's Republic of China
,
Bin Meng
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, People's Republic of China
,
Jun Liu
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, People's Republic of China
,
Lixiang Wang
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, People's Republic of China
› Institutsangaben
Funding Information The authors are grateful for the financial supports by the Natural Science Foundation of China (No. 21625403, 21875244, 21875241, 51603203, and 21761132020).
Weitere Informationen

Publikationsverlauf

Received: 29. September 2019

Accepted after revision: 29. Oktober 2019

Publikationsdatum:
27. Dezember 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.


Supporting Information

 
  • 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