Citation: Chenyi Yang, Shaoqing Zhang, Junzhen Ren, Pengqing Bi, Xiaotao Yuan, Jianhui Hou. Fluorination strategy enables greatly improved performance for organic solar cells based on polythiophene derivatives[J]. Chinese Chemical Letters, ;2021, 32(7): 2274-2278. doi: 10.1016/j.cclet.2021.03.006 shu

Fluorination strategy enables greatly improved performance for organic solar cells based on polythiophene derivatives

Chenyi Yang ^{a, b} ,
Shaoqing Zhang ^{a, b, *,} ,
Junzhen Ren ^b ,
Pengqing Bi ^b ,
Xiaotao Yuan ^{a, *,} ,
Jianhui Hou ^{a, b}

a.
School of Chemistry and Biology Engineering, University of Science and Technology Beijing, Beijing 100083, China
b.
State Key Laboratory of Polymer Physics and Chemistry, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

shaoqingz@iccas.ac.cn

yuanxt@ustb.edu.cn

Received Date: 10 February 2021
Revised Date: 1 March 2021
Accepted Date: 2 March 2021
Available Online: 4 March 2021

Figures(5)

The power conversion efficiencies (PCEs) of organic solar cells (OSCs) have reached 18% recently, which have already met the demand of practical application. However, these outstanding results were generally achieved with donor-acceptor (D-A) type copolymer donors, which can hardly fulfill the low-cost large-scale production due to their complicated synthesis processes. Therefore, developing polymer donors with simple chemical structures is urgent for realizing low-cost OSCs. Polythiophene (PT) derivatives are currently regarded as promising candidates for such kind of donor materials, which has been illustrated in many works. In this work, two new alkylthio substituted PT derivatives, P301 and P302, were synthesized and tested as donors in the OSCs using Y5 as the acceptor. In comparison, the introduction of fluorine atoms on the backbone of P302 can not only downshift the energy levels, but also greatly improve the phase separation morphologies of the active layers, which is ascribed to the enhanced aggregation effect and the reduced miscibility with the non-fullerene acceptor. As a result, the P302:Y5-based OSC exhibits a significantly improved PCE of 9.65% than that of P301:Y5-based one, indicating the important role of fluorination in the construction of efficient PT derivative donors.
- Organic solar cells,
- Polythiophene derivatives,
- Fluorination,
- Aggregation effect,
- Miscibility
1. [1]
  R. Søndergaard, M. Hösel, D. Angmo, T.T. Larsen-Olsen, F.C. Krebs, Mater. Today 15 (2012) 36-49. doi: 10.1016/S1369-7021(12)70019-6
2. [2]
  O. Inganas, Adv. Mater. 30 (2018) e1800388. doi: 10.1002/adma.201800388
3. [3]
  H. Kang, G. Kim, J. Kim, et al., Adv. Mater. 28 (2016) 7821-7861. doi: 10.1002/adma.201601197
4. [4]
  G. Li, R. Zhu, Y. Yang, Nat. Photonics 6 (2012) 153-161. doi: 10.1038/nphoton.2012.11
5. [5]
  Y. Li, Acc. Chem. Res. 45 (2012) 723-733. doi: 10.1021/ar2002446
6. [6]
  H. Yao, L. Ye, H. Zhang, et al., Chem. Rev. 116 (2016) 7397-7457. doi: 10.1021/acs.chemrev.6b00176
7. [7]
  J. Hou, O. Inganas, R.H. Friend, F. Gao, Nat. Mater. 17 (2018) 119-128. doi: 10.1038/nmat5063
8. [8]
  A. Wadsworth, M. Moser, A. Marks, et al., Chem. Soc. Rev. 48 (2018) 1596-1625. doi: 10.1039/c7cs00892a
9. [9]
  X. Xu, G. Zhang, Y. Li, Q. Peng, Chin. Chem. Lett. 30 (2019) 809-825. doi: 10.1016/j.cclet.2019.02.030
10. [10]
  W. Zhao, D. Qian, S. Zhang, et al., Adv. Mater. 28 (2016) 4734-4739. doi: 10.1002/adma.201600281
11. [11]
  S. Zhang, Y. Qin, J. Zhu, J. Hou, Adv. Mater. 30 (2018) e1800868. doi: 10.1002/adma.201800868
12. [12]
  J. Yuan, Y. Zhang, L. Zhou, et al., Joule 3 (2019) 1140-1151. doi: 10.1016/j.joule.2019.01.004
13. [13]
  Y. Cui, H. Yao, J. Zhang, et al., Adv. Mater. 2020, e1908205.
14. [14]
  Q. Liu, Y. Jiang, K. Jin, et al., Sci. Bull. 65 (2020) 272-275. doi: 10.1016/j.scib.2020.01.001
15. [15]
  R. Po, A. Bernardi, A. Calabrese, et al., Energy Environ. Sci. 7 (2014) 925-943. doi: 10.1039/c3ee43460e
16. [16]
  S. Holliday, R.S. Ashraf, A. Wadsworth, et al., Nat. Commun. 7 (2016) 11585. doi: 10.1038/ncomms11585
17. [17]
  A. Marrocchi, D. Lanari, A. Facchetti, L. Vaccaro, Energy Environ. Sci. 5 (2012) 8457-8474. doi: 10.1039/c2ee22129b
18. [18]
  P. Ye, Y. Chen, J. Wu, et al., Mater. Chem. Front. 3 (2019) 64-69. doi: 10.1039/c8qm00461g
19. [19]
  B. Xiao, A. Tang, L. Cheng, et al., Sol. RRL 1 (2017) 1700166. doi: 10.1002/solr.201700166
20. [20]
  F. Liu, J. Zhang, Z. Zhou, et al., J. Mater. Chem. A 5 (2017) 16573-16579. doi: 10.1039/C7TA05108E
21. [21]
  Q. Xu, C. Chang, W. Li, et al., Acta Phys. Chim. Sin. 35 (2019) 268-274. doi: 10.3866/pku.whxb201803261
22. [22]
  Y. Qin, M.A. Uddin, Y. Chen, et al., Adv. Mater. 28 (2016) 9416-9422. doi: 10.1002/adma.201601803
23. [23]
  H. Yao, D. Qian, H. Zhang, et al., Chin. J. Chem. 36 (2018) 491-494. doi: 10.1002/cjoc.201800015
24. [24]
  Q. Wang, M. Li, X. Zhang, et al., Macromolecules 52 (2019) 4464-4474. doi: 10.1021/acs.macromol.9b00793
25. [25]
  C. Yang, N. Liang, L. Ye, et al., Org. Electron. 68 (2019) 15-21.
26. [26]
  C. Yang, S. Zhang, J. Ren, et al., Energy Environ. Sci. 13 (2020) 2864-2869. doi: 10.1039/d0ee01763a
27. [27]
  X. Wu, T. Chen, R.D. Rieke, Macromolecules 29 (1996) 7671-7677. doi: 10.1021/ma960946m
28. [28]
  C.A. Cutler, A.K. Burrell, D.L. Officer, C.O. Too, G.G. Wallace, Synth Met. 128 (2002) 35-42. doi: 10.1016/S0379-6779(01)00661-0
29. [29]
  L. Huo, Y. Zhou, Y. Li, Macromol. Rapid Commun. 30 (2009) 925-931. doi: 10.1002/marc.200800785
30. [30]
  Y. Liu, J. Zhao, Z. Li, et al., Nat. Commun. 5 (2014) 5293. doi: 10.1038/ncomms6293
31. [31]
  D. Qian, L. Ye, M. Zhang, et al., Macromolecules 45 (2012) 9611-9617. doi: 10.1021/ma301900h
32. [32]
  Z. Zheng, H. Yao, L. Ye, et al., Mater. Today 35 (2020) 115-130. doi: 10.1016/j.mattod.2019.10.023
33. [33]
  S. Zhang, Y. Qin, M.A. Uddin, et al., Macromolecules 49 (2016) 2993-3000. doi: 10.1021/acs.macromol.6b00248
34. [34]
  G. Yang, Z. Li, K. Jiang, et al., Sci. China Chem. 60 (2017) 545-551. doi: 10.1007/s11426-016-0378-y
35. [35]
  J.T. Blaskovits, T. Bura, S Beaupré, et al., Macromolecules 50 (2017) 162-174. doi: 10.1021/acs.macromol.6b02365
36. [36]
  A. He, Y. Qin, W. Dai, D. Zhou, J. Zou, Chin. Chem. Lett. 30 (2019) 2263-2265. doi: 10.1016/j.cclet.2019.07.018
37. [37]
  W. Zhao, S. Li, H. Yao, et al., J. Am. Chem. Soc. 139 (2017) 7148-7151. doi: 10.1021/jacs.7b02677
38. [38]
  J. Yuan, Y. Zhang, L. Zhou, et al., Adv. Mater. 31 (2019) 1807577. doi: 10.1002/adma.201807577
39. [39]
  J.L. Wu, F.C. Chen, Y.S. Hsiao, et al., ACS Nano 5 (2011) 959-967. doi: 10.1021/nn102295p
40. [40]
  M. Lenes, M. Morana, C.J. Brabec, P.W.M. Blom, Adv. Funct. Mater. 19 (2009) 1106-1111. doi: 10.1002/adfm.200801514
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