Citation: Luo Mei, Zhu Can, Yuan Jun, Zhou Liuyang, Keshtov M.L., Yu Godovsky D., Zou Yingping. A chlorinated non-fullerene acceptor for efficient polymer solar cells[J]. Chinese Chemical Letters, ;2019, 30(12): 2343-2346. doi: 10.1016/j.cclet.2019.07.023 shu

A chlorinated non-fullerene acceptor for efficient polymer solar cells

Luo Mei ^a ,
Zhu Can ^a ,
Yuan Jun ^a ,
Zhou Liuyang ^a ,
Keshtov M.L. ^b ,
Yu Godovsky D. ^b ,
Zou Yingping ^a,*,

a.
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China
b.
Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991, Russia

yingpingzou@csu.edu.cn

Received Date: 17 June 2019
Revised Date: 8 July 2019
Accepted Date: 9 July 2019
Available Online: 9 December 2019

Figures(4)

Improving the performance and reducing the manufacturing costs are the main directions for the development of organic solar cells in the future. Here, the strategy that uses chemical structure modification to optimize the photoelectric properties is reported. A new narrow bandgap (1.30 eV) chlorinated non-fullerene electron acceptor (Y15), based on benzo[d] [1, 2, 3] triazole triazole with two 3-undecylthieno[2', 3':4, 5] thieno[3, 2-b] pyrrole fused -7-heterocyclic ring, with absorption edge extending to the near-infrared (NIR) region, namely A-DA'D-A type structure, is designed and synthesized. Its electrochemical and optoelectronic properties are systematically investigated. Benefitting from its NIR light harvesting, the fabricated photovoltaic devices based on Y15 deliver a high power conversion efficiency (PCE) of 14.13%, when blending with a wide bandgap polymer donor PM6. Our results show that the A-DA'D-A type molecular design and application of near-infrared electron acceptors have the potential to further improve the PCE of polymer solar cells (PSCs).
- Electron acceptor Y15,
- Chlorinated,
- Non-fullerene electron acceptors,
- Efficient polymer solar cells,
- Narrow bandgap
1. [1]
  Z. Zhang, Z. Zhou, Q. Hu, et al., ACS Appl. Mater. Interfaces 9 (2017) 6213-6219.
2. [2]
  Y. Liu, M. Li, X. Zhou, et al., ACS Energy Lett. 3 (2018) 1832-1839. doi: 10.1021/acsenergylett.8b00928
3. [3]
  Q. Fan, Y. Wang, M. Zhang, et al., Adv. Mater. 30 (2018) 1704546. doi: 10.1002/adma.201704546
4. [4]
  L. Gao, Z.G. Zhang, H. Bin, et al., Adv. Mater. 28 (2016) 8288-8295. doi: 10.1002/adma.201601595
5. [5]
  J. Yuan, Y. Zhang, L. Zhou, et al., Joule 3 (2019) 1140-1151. doi: 10.1016/j.joule.2019.01.004
6. [6]
  L.X. Meng, Y.M. Zhang, X.J. Wan, et al., Science 361 (2018) 1094-1098. doi: 10.1126/science.aat2612
7. [7]
  Y. Guo, Y. Li, O. Awartani, et al., Adv. Mater. 29 (2017) 1700309. doi: 10.1002/adma.201700309
8. [8]
  B. Kan, J. Zhang, F. Liu, et al., Adv. Mater. 30 (2018) 1704904. doi: 10.1002/adma.201704904
9. [9]
  Y. Lin, J. Wang, Z.G. Zhang, et al., Adv. Mater. 27 (2015) 1170-1174. doi: 10.1002/adma.201404317
10. [10]
  J. Roncali, P. Leriche, P. Blanchard, Adv. Mater. 26 (2014) 3821-3838. doi: 10.1002/adma.201305999
11. [11]
  W. Ni, X. Wan, M. Li, Y. Wang, Y. Chen, Chem. Commun. (Camb.) 51 (2015) 4936-4950. doi: 10.1039/C4CC09758K
12. [12]
  L. Dou, Y. Liu, Z. Hong, G. Li, Y. Yang, Chem. Rev. 115 (2015) 12633-12665. doi: 10.1021/acs.chemrev.5b00165
13. [13]
  Z. Zhang, J. Yu, X. Yin, et al., Adv. Funct. Mater. 28 (2018) 1705095. doi: 10.1002/adfm.201705095
14. [14]
  B. Huang, L. Chen, X. Jin, et al., Adv. Funct. Mater. 28 (2018) 1800606. doi: 10.1002/adfm.201800606
15. [15]
  J. Wang, W. Gao, Q. An, et al., J. Mater. Chem. A Mater. Energy Sustain. 6 (2018) 11751-11758. doi: 10.1039/C8TA03453B
16. [16]
  Q. An, W. Gao, F. Zhang, et al., J. Mater. Chem. A Mater. Energy Sustain. 6 (2018) 2468-2475. doi: 10.1039/C7TA10763C
17. [17]
  Y. Li, L. Zhong, B. Gautam, et al., Energy Environ. Sci. 10 (2017) 1610-1620. doi: 10.1039/C7EE00844A
18. [18]
  W. Zhao, S. Li, H. Yao, et al., J. Am. Chem. Soc. 139 (2017) 7148-7151. doi: 10.1021/jacs.7b02677
19. [19]
  H. Yao, Y. Cui, R. Yu, et al., Angew. Chem. Int. Ed. 56 (2017) 3045-3049. doi: 10.1002/anie.201610944
20. [20]
  W. Gao, T. Liu, C. Zhong, et al., ACS Energy Lett. 3 (2018) 1760-1768. doi: 10.1021/acsenergylett.8b00825
21. [21]
  X. Wang, Z. Du, K. Dou, et al., Adv. Energy Mater. 9 (2019) 1802530.
22. [22]
  C. Li, T. Xia, J. Song, et al., J. Mater. Chem. A Mater. Energy Sustain. 7 (2019) 1435-1441. doi: 10.1039/C8TA11197A
23. [23]
  W. Zhong, J. Cui, B. Fan, et al., Chem. Mater. 29 (2017) 8177-8186. doi: 10.1021/acs.chemmater.7b02228
24. [24]
  B. Kan, H. Feng, H. Yao, et al., Sci. China Chem. 61 (2018) 1307-1313. doi: 10.1007/s11426-018-9334-9
25. [25]
  Y. Cui, H. Yao, B. Gao, et al., J. Am. Chem. Soc. 139 (2017) 7302-7309. doi: 10.1021/jacs.7b01493
26. [26]
  S. Li, L. Ye, W. Zhao, et al., Adv. Energy Mater. 7 (2017) 1700183.
27. [27]
  J. Yuan, T. Huang, P. Cheng, et al., Nat. Commun. 10 (2019) 570. doi: 10.1038/s41467-019-08386-9
28. [28]
  J. Yuan, Y. Zhang, L. Zhou, et al., Adv. Mater. 31 (2019) e1807577. doi: 10.1002/adma.201807577
29. [29]
  Y. Cui, C. Yang, H. Yao, et al., Adv. Mater. 29 (2017) 1703080. doi: 10.1002/adma.201703080
30. [30]
  H. Zhang, H. Yao, J. Hou, et al., Adv. Mater. 30 (2018) e1800613. doi: 10.1002/adma.201800613
31. [31]
  S.-S. Wan, X. Xu, J.-L. Wang, et al., J. Mater. Chem. A Mater. Energy Sustain. 7 (2019) 11802-11813. doi: 10.1039/C9TA03177D
32. [32]
  D. Mo, H. Wang, H. Chen, et al., Chem. Mater. 29 (2017) 2819-2830. doi: 10.1021/acs.chemmater.6b04828
33. [33]
  J. Qu, Q. Zhao, J. Zhou, et al., Chem. Mater. 31 (2019) 1664-1671. doi: 10.1021/acs.chemmater.8b05047
34. [34]
  M.L. Tang, J.H. Oh, A.D. Reichardt, et al., J. Am. Chem. Soc. 131 (2009) 3733-3740. doi: 10.1021/ja809045s
35. [35]
  J.H. Oh, S.-L. Suraru, W.-Y. Lee, et al., Adv. Funct. Mater. 20 (2010) 2148-2156. doi: 10.1002/adfm.201000425
36. [36]
  H.H. Gao, Y. Sun, Y. Cai, et al., Adv. Energy Mater. (2019) 1901024.
37. [37]
  D. Liu, L. Yang, Y. Wu, et al., Chem. Mater. 30 (2018) 619-628. doi: 10.1021/acs.chemmater.7b03142
38. [38]
  Y. Chen, Y. Geng, A. Tang, et al., Chem. Commun. (Camb.) 55 (2019) 6708-6710. doi: 10.1039/C9CC02904D
39. [39]
  M. Zhang, X. Guo, W. Ma, H. Ade, J. Hou, Adv. Mater. 27 (2015) 4655-4660. doi: 10.1002/adma.201502110
40. [40]
  J. Sun, Z. Zhang, X. Yin, et al., J. Mater. Chem. A Mater. Energy Sustain. 6 (2018) 2549-2554. doi: 10.1039/C7TA10391C
41. [41]
  Z. Zhang, L. Feng, S. Xu, et al., J. Mater. Chem. A Mater. Energy Sustain. 5 (2017) 11286-11293. doi: 10.1039/C7TA02486J
42. [42]
  Y. Gao, Z. Wang, G. Yue, et al., Sol. RRL (2019) 1900012.
43. [43]
  X. Li, T. Yan, H. Bin, et al., J. Mater. Chem. A Mater. Energy Sustain. 5 (2017) 22588-22597. doi: 10.1039/C7TA07049G
44. [44]
  T. Li, S. Dai, Z. Ke, et al., Adv. Mater. 30 (2018) 1705969. doi: 10.1002/adma.201705969
45. [45]
  H. Xu, Y. Yang, C. Zhong, et al., J. Mater. Chem. A Mater. Energy Sustain. 6 (2018) 6393-6401. doi: 10.1039/C8TA00704G
46. [46]
  Y. Wu, H. Bai, Z. Wang, et al., Energy Environ. Sci. 8 (2015) 3215-3221. doi: 10.1039/C5EE02477C
47. [47]
  Y. Li, L. Zhong, F.P. Wu, et al., Energy Environ. Sci. 9 (2016) 3429-3435. doi: 10.1039/C6EE00315J
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