CC BY-NC-ND 4.0 · Organic Materials 2020; 02(01): 026-032
DOI: 10.1055/s-0039-3402514
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 Side-Chain Variation on Single-Crystalline Structures for Revealing the Structure–Property Relationships of Organic Solar Cells

a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
b  School of Chemical Science, University of Chinese Academy of Sciences, Beijing, China
,
Liu Yuan
a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
,
Ruimin Zhou
a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
c  Sino-Danish Center for Education and Research, Sino-Danish College, University of Chinese Academy of Sciences, Beijing, China
,
Zhen Wang
a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
b  School of Chemical Science, University of Chinese Academy of Sciences, Beijing, China
,
a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
,
Yajie Zhang
a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
,
Kun Lu
a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
,
a  CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing, China
› Author Affiliations
Funding InformationThe authors acknowledge the financial support from the National Natural Science Foundation of China (Grant Nos. 21822503, 21534003, 21125420, and 91427302), the Ministry of Science and Technology of China (Grant Nos. 2016YFA0200704 and 2016YFF0203803), the Beijing Nova Program (Grant No. Z17110001117062), and the Chinese Academy of Sciences.
Further Information

Publication History

23 September 2019

08 November 2019

Publication Date:
30 January 2020 (online)


Abstract

The molecular stacking assembly in the active layer plays a significant role in the photovoltaic performance of organic solar cells (OSCs). Here, we report two new small molecular donors with different side chains, FBT-O and FBT-H, and their corresponding fullerene-based OSCs. A slight change in the side chains led to a big difference in the power conversion efficiencies (PCEs). Although the molecular structures of the two donors are similar to each other, PCEs of the devices based on FBT-O were almost three times higher than those of the devices based on FBT-H, with manifold short-circuit current density, fill factor, as well as three orders of magnitude enhancement in the hole mobility. The difference in their single crystal structures was thoroughly investigated, whereby the FBT-O exhibited better planarity leading to appropriate phase separation and domain size. Furthermore, two-dimensional grazing-incidence wide-angle X-ray scattering results of the blend films revealed that the two donors retained a similar stacking structure as compared to the single-crystal structures, thus, establishing a clear relationship between the molecular stacking structure and the device performance.

Supporting Information

 
  • References

  • 1 Deng D, Zhang Y-J, Zhang J-Q, Wang Z-Y, Zhu L-Y, Fang J, Xia B-Z, Wang Z, Lu K, Ma W, Wei Z-X. Nat. Commun. 2016; 7: 13740
  • 2 Yuan L, Lu K, Xia B-Z, Zhang JQ, Wang Z, Wang Z-Y, Deng D, Fang J, Zhu L-Y, Wei Z-X. Adv. Mater. 2016; 28: 5980
  • 3 Yuan L, Zhao Y-F, Zhang J-Q, Zhang Y-J, Zhu L-Y, Lu K, Yan W, Wei Z-X. Adv. Mater. 2015; 27: 4229
  • 4 Deng D, Zhang Y, Wang Z, Wu Q, Ma W, Lu K, Wei Z-X. Asian J. Org. Chem. 2018; 7: 558
  • 5 Li H, Wu Q, Zhou R-M, Shi Y-N, Yang C, Zhang YJ, Zhang J-Q, Zou W-J, Deng D, Lu K, Wei Z-X. Adv. Energy Mater. 2019; 9: 1803175
  • 6 Che X-Z, Li Y-X, Qu Y, Forrest SR. Nat. Energy 2018; 3: 422
  • 7 Yuan J, Zhang Y-Q, Zhou L-Y, Zhang G-C, Yip H-L, Lau T-K, Lu X-H, Zhu C, Peng H-J, Johnson PA, Leclerc M, Cao Y, Ulanski J, Li YF, Zou Y-P. Joule 2019; 3: 1140
  • 8 Meng L-X, Zhang Y-M, Wan X-J, Li C-X, Zhang X, Wang Y-B, Ke X, Xiao Z, Ding L-M, Xia R-X, Yip H-L, Cao Y, Chen Y-S. Science 2018; 361: 1094
  • 9 Zhang M-J, Guo X, Ma W, Ade H, Hou J-H. Adv. Mater. 2015; 27: 4655
  • 10 Li S-S, Ye L, Zhao W-C, Yan H-P, Yang B, Liu D-L, Li W-N, Ade H, Hou J-H. J. Am. Chem. Soc. 2018; 140: 7159
  • 11 Xu X-P, Yu T, Bi Z-Z, Ma W, Li Y, Peng Q. Adv. Mater. 2018; 30: 1703973
  • 12 Liu D-L, Yang B, Jang B-M, Xu B-W, Zhang S-Q, He C, Woo HY, Hou J-H. Energy Environ. Sci. 2017; 10: 546
  • 13 Wu Y-N, An C-B, Shi L-L, Yang L-Y, Qin Y-P, Liang N-N, He C, Wang Z-H, Hou J-H. Angew. Chem. Int. Ed. 2018; 57: 12911
  • 14 Li H, Zhao Y-F, Fang J, Zhu X-W, Xia B-Z, Lu K, Wang Z, Zhang J-Q, Guo X-F, Wei Z-X. Adv. Energy Mater. 2018; 8: 1702377
  • 15 Deng D, Yang Y, Zou W-J, Zhang Y-J, Wang Z, Wang Z-Y, Zhang J-Q, Lu K, Ma W, Wei Z-X. J. Mater. Chem. A 2018; 6: 22077
  • 16 Zhou R-M, Xia B-Z, Li H, Wang Z, Yang Y, Zhang J-Q, Laursen BW, Lu K, Wei Z-X. Front. Chem. 2018; 6: 384
  • 17 Yang L-Y, Zhang S-Q, He C, Zhang J-Q, Yang Y, Zhu J, Cui Y, Zhao W-C, Zhang H, Zhang Y, Wei Z-X, Hou JH. Chem. Mater. 2018; 30: 2129
  • 18 Li X-X, Wang Y, Zhu Q-L, Guo X, Ma W, Ou X-M, Zhang M-J, Li Y-F. J. Mater. Chem. A 2019; 7: 3682
  • 19 Qiu B-B, Chen S-S, Xue L-W, Sun C-K, Li X-J, Zhang Z-G, Yang C-D, Li Y-F. Front. Chem. 2018; 6: 413
  • 20 Guo J, Bin H-J, Wang W, Chen B-C, Guo J, Sun R, Zhang Z-G, Jiao X-C, Li Y-F, Min J. J. Mater. Chem. A 2018; 6: 15675
  • 21 Yuan L, Lu K, Xia B-Z, Zhang J-Q, Wang Z, Wang Z-Y, Deng D, Fang J, Zhu L-Y, Wei Z-X. Adv. Mater. 2016; 28: 5980
  • 22 Yang L-Y, Zhang S-Q, He C, Zhang J-Q, Yao H-F, Yang Y, Zhang Y, Zhao W-C, Hou J-H. J. Am. Chem. Soc. 2017; 139: 1958
  • 23 Wei H, Chen W-C, Han L-L, Wang T, Bao X-C, Li X-Y, Liu J, Zhou Y-H, Yang R-Q. Chem. Asian J. 2015; 10: 1791
  • 24 Duan R-M, Cui Y, Zhao Y-F, Li C, Chen L, Hou J-H, Wagner M, Baumgarten M, He C, Muellen K. ChemSusChem 2016; 9: 973
  • 25 Duan T-N, Tang H, Liang R-Z, Lv J, Kan Z-P, Singh R, Kumar M, Xiao Z-Y, Lu S-R, Laquai F. J. Mater. Chem. A 2019; 7: 2541
  • 26 Kim SW, Lee YJ, Lee YW, Koh CW, Lee Y, Kim MJ, Liao K, Cho JH, Kim BJ, Woo HY. ACS Appl. Mater. Interfaces 2018; 10: 39952
  • 27 Chen X-J, Feng H-R, Lin Z-J, Jiang Z-W, He T, Yin S-C, Wan X-J, Chen Y-S, Zhang Q, Qiu H-Y. Dyes Pigm. 2017; 147: 183
  • 28 Yang L-Y, Zhang S-Q, He C, Zhang J-Q, Yang Y, Zhu J, Cui Y, Zhao W-C, Zhang H, Zhang Y, Wei Z-X, Hou J-H. Chem. Mater. 2018; 30: 2129
  • 29 Hong J, Sung M-J, Cha H, Park CE, Durrant JR, An TK, Kim YH, Kwon SK. ACS Appl. Mater. Interfaces 2018; 10: 36037
  • 30 Yao X, Shao W, Xiang X, Xiao W-J, Liang L, Zhao F-G, Ling J, Lu Z-Q, Li J-J, Li W-S. Org. Electron. 2018; 61: 56
  • 31 Kumari T, Lee SM, Lee KC, Cho Y, Yang C. Adv. Energy Mater. 2018; 8: 1800616
  • 32 Min J, Kwon OK, Cui C-H, Park JH, Wu Y, Park SY, Li Y-F, Brabec CJ. J. Mater. Chem. A 2016; 4: 14234
  • 33 Aldrich TJ, Matta M, Zhu W, Swick SM, Stern CL, Schatz GC, Facchetti A, Melkonyan FS, Marks TJ. J. Am. Chem. Soc. 2019; 141: 3274
  • 34 Qu J-F, Chen H, Zhou J-D, Lai H-J, Liu T, Chao P-J, Li D-N, Xie Z-Q, He F, Ma Y-G. ACS Appl. Mater. Interfaces 2018; 10: 39992
  • 35 Swick SM, Zhu W, Matta M, Aldrich TJ, Harbuzaru A, Lopez Navarrete JT, Ponce Ortiz R, Kohlstedt KL, Schatz GC, Facchetti A, Melkonyan FS, Marks TJ. Proc. Natl. Acad. Sci. U.S.A. 2018; 115: E8341
  • 36 Shi X-L, Zuo L-J, Jo SB, Gao K, Lin F, Liu F, Jen AKY. Chem. Mater. 2017; 29: 8369
  • 37 Han G-C, Guo Y, Song X-X, Wang Y, Yi Y-P. J. Mater. Chem. C 2017; 5: 4852
  • 38 McDowell C, Narayanaswamy K, Yadagiri B, Gayathri T, Seifrid M, Datt R, Ryno SM, Heifner MC, Gupta V, Risko C, Singh SP, Bazan GC. J. Mater. Chem. A 2018; 6: 383
  • 39 Sun K, Xiao Z-Y, Lu S-R, 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