Citation: WU Yi, KONG Jingyi, QIN Yunpeng, YAO Huifeng, ZHANG Shaoqing, HOU Jianhui. Realizing Green Solvent Processable Non-fullerene Organic Solar Cells by Modulating the Side Groups of Conjugated Polymers[J]. Acta Physico-Chimica Sinica, ;2019, 35(12): 1391-1398. doi: 10.3866/PKU.WHXB201904037 shu

Realizing Green Solvent Processable Non-fullerene Organic Solar Cells by Modulating the Side Groups of Conjugated Polymers

WU Yi ¹ ,
KONG Jingyi ¹ ,
QIN Yunpeng ¹ ,
YAO Huifeng ² ,
ZHANG Shaoqing ^1,, ,
HOU Jianhui ^1,2

1.
Department of Chemical and Biological Engineering, University of Science & Technology Beijing, Beijing 100083, P. R. China
2.
Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China

Corresponding author: ZHANG Shaoqing, shaoqingz@ustb.edu.cn
Received Date: 8 April 2019
Revised Date: 15 May 2019
Accepted Date: 15 May 2019
Available Online: 23 December 2019
Fund Project: the National Science and Technology Major Project of the Ministry of Science and Technology of China 2016YFC0700603the National Natural Science Foundation of China 21704004the Fundamental Research Funds for the Central Universities, China FRF-TP-17-009A1The project was supported by the National Natural Science Foundation of China (21704004), the National Science and Technology Major Project of the Ministry of Science and Technology of China (2016YFC0700603), and the Fundamental Research Funds for the Central Universities, China (FRF-TP-17-009A1)

Organic solar cells (OSCs) are a promising next-generation photovoltaic technology that can be used to harvest clean and renewable solar energy. OSCs are typically composed of donor:acceptor blends as photo-active materials. Compared to the conventional inorganic silicon solar cells, OSCs are suitable for large-scale production using roll-to-roll technology, promising low-cost and the potential to avoid environmental pollution. The last few years have witnessed the rapid development of OSCs. The power conversion efficiencies (PCEs) of OSCs have surpassed ~14%–16%, benefiting from the design of novel materials, optimization of blend morphology, and deep understanding of the charge generation mechanism. Currently, the most widely used processing solvents for preparing high-efficient OSCs are chlorinated or aromatic solvents including chlorobenzene, dichlorobenzene, and chloroform, which are highly detrimental to the environment and human health, and may not be utilized for future in industry. Thus, replacing these highly toxic solvents with environmentally friendly alternatives called "green solvents" is an important topic in OSC research. Herein, poly[(2, 6-(4, 8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1, 2-b:4, 5-b′]dithiophene)-co-(1, 3-di(5-thiophene-2-yl)-5, 7-bis(2-ethylhexyl)benzo[1, 2-c:4, 5-c′]dithiophene-4, 8-dione)] (PBDB-T) was used as a reference material to design and synthesize a novel conjugated polymer (PBDB-DT) by extending the alkyl side chains and enlarging the conjugated side groups. The thermal stability of the polymer donor was examined via thermogravimetric analysis, showing that the polymers exhibit very good stability at > 400 ℃. Importantly, PBDB-DT exhibits good solubility in low-toxic solvent tetrahydrofuran (THF) due to its longer alkyl side chains, and shows a strong aggregation effect in THF due to the larger conjugated side groups. A favorable PCE of 10.2% was achieved for the THF-processed PBDB-DT:IT-M based OSC device. In contrast, PBDB-T has limited solubility in THF. The solar cell device based on PBDB-T:IT-M delivered a moderate PCE of 6.41%. The investigation of blend morphology via atomic force microscope suggested that the PBDB-DT:IT-M has a smooth surface, which is favorable for charge generation and transport. These results demonstrate that molecular optimization is a promising strategy to modulate the solubility and achieve high efficiency for organic photovoltaic materials processed using green solvents.
- Conjugated polymer,
- Non-fullerene acceptor,
- Organic solar cell,
- Green solvent,
- Molecular design
1. [1]
  Li, Y. Polym. Bull. 2011, 10, 33. doi: 10.14028/j.cnki.1003-3726.2011.10.017 doi: 10.14028/j.cnki.1003-3726.2011.10.017
2. [2]
  Fu, Y.; Wang, F.; Zhang, Y.; Fang, X.; Lai, W.; Huang, W. Acta Chim. Sin. 2014, 72, 158. doi: 10.6023/a13111142 doi: 10.6023/a13111142
3. [3]
  Yao, H.; Hou, J. Acta Polym. Sin. 2016, 11, 1468. doi: 10.11777/j.issn1000-3304.2016.16216 doi: 10.11777/j.issn1000-3304.2016.16216
4. [4]
  Duan, C.; Huang, F.; Cao, Y. J. Mater. Chem. 2012, 22, 10416. doi: 10.1039/C2JM30470H doi: 10.1039/C2JM30470H
5. [5]
  Olle, I. Adv. Mater. 2018, 30, 1800388. doi: 10.1002/adma.201800388 doi: 10.1002/adma.201800388
6. [6]
  Dou, C.; Liu, J.; Wang, L. Sci. China Chem. 2017, 60, 450. doi: 10.1007/s11426-016-0503-x doi: 10.1007/s11426-016-0503-x
7. [7]
  Fan, H.; Zhu, X. Sci. China Chem. 2015, 58, 922. doi: 10.1007/s11426-015-5418-6 doi: 10.1007/s11426-015-5418-6
8. [8]
  Jia, B.; Wu, Y.; Zhao, F.; Yan, C.; Zhu, S.; Cheng, P.; Mai, J.; Lau, T. K.; Lu, X.; Su, C. J.; et al. Sci. China Chem. 2017, 60, 257. doi: 10.1007/s11426-016-0336-6
9. [9]
  Kan, B.; Feng, H.; Yao, H.; Chang, M.; Wan, X.; Li, C.; Hou, J.; Chen, Y. Sci. China Chem. 2018, 61, 1307. doi: 10.1007/s11426-018-9334-9 doi: 10.1007/s11426-018-9334-9
10. [10]
  Fan, Q.; Su, W.; Wang, Y.; Guo, B.; Jiang, Y.; Guo, X.; Liu, F.; Russell, T. P.; Zhang, M.; Li, Y. Sci. China Chem. 2018, 61, 531. doi: 10.1007/s11426-017-9199-1 doi: 10.1007/s11426-017-9199-1
11. [11]
  Heeger, A. J. Adv. Mater. 2014, 26, 10. doi: 10.1002/adma.201304373 doi: 10.1002/adma.201304373
12. [12]
  Li, G.; Zhu, R.; Yang, Y. Nat. Photonics 2012, 6, 153. doi: 10.1038/nphoton.2012.11 doi: 10.1038/nphoton.2012.11
13. [13]
  Chen, J. D.; Cui, C.; Li, Y. Q.; Zhou, L.; Ou, Q. D.; Li, C.; Li, Y.; Tang, J. X. Adv. Mater. 2015, 27, 1035. doi: 10.1002/adma.201404535 doi: 10.1002/adma.201404535
14. [14]
  Zhang, S. Q.; Ye, L.; Zhao, W. C.; Yang, B.; Wang, Q.; Hou, J. H. Sci. China Chem. 2015, 58, 248. doi: 10.1007/s11426-014-5273-x doi: 10.1007/s11426-014-5273-x
15. [15]
  Liu, Y.; Zhao, J.; Li, Z.; Mu, C.; Ma, W.; Hu, H.; Jiang, K.; Lin, H.; Ade, H.; Yan, H. Nat. Commun. 2014, 5, 5293. doi: 10.1038/ncomms6293 doi: 10.1038/ncomms6293
16. [16]
  He, Z.; Xiao, B.; Liu, F.; Wu, H.; Yang, Y.; Xiao, S.; Wang, C.; Russell, T. P.; Cao, Y. Nat. Photonics 2015, 9, 174. doi: 10.1038/nphoton.2015.6 doi: 10.1038/nphoton.2015.6
17. [17]
  He, Z.; Zhong, C.; Su, S.; Xu, M.; Wu, H.; Cao, Y. Nat. Photonics 2012, 6, 591. doi: 10.1038/NPHOTON.2012.190 doi: 10.1038/NPHOTON.2012.190
18. [18]
  Li, M.; Gao, K.; Wan, X.; Zhang, Q.; Kan, B.; Xia, R.; Liu, F.; Yang, X.; Feng, H.; Ni, W.; et al. Nat. Photonics 2016, 11, 85. doi: 10.1038/nphoton.2016.240
19. [19]
  Ouyang, X.; Peng, R.; Ai, L.; Zhang, X.; Ge, Z. Nat. Photonics 2015, 9, 520. doi: 10.1038/nphoton.2015.126 doi: 10.1038/nphoton.2015.126
20. [20]
  Zhao, J.; Li, Y.; Yang, G.; Jiang, K.; Lin, H.; Ade, H.; Ma, W.; Yan, H. Nat. Energy 2016, 1, 15027. doi: 10.1038/nenergy.2015.27 doi: 10.1038/nenergy.2015.27
21. [21]
  Deng, D.; Zhang, Y.; Zhang, J.; Wang, Z.; Zhu, L.; Fang, J.; Xia, B.; Wang, Z.; Lu, K.; Ma, W.; et al. Nat. Commun. 2016, 7, 13740. doi: 10.1038/ncomms13740
22. [22]
  Zhang, H.; Yao, H.; Hou, J.; Zhu, J.; Zhang, J.; Li, W.; Yu, R.; Gao, B.; Zhang, S.; Hou, J. Adv. Mater. 2018, 30, e1800613. doi: 10.1002/adma.201800613 doi: 10.1002/adma.201800613
23. [23]
  Yuan, J.; Zhang, Y.; Zhou, L.; Zhang, G.; Yip, H. L.; Lau, T. K.; Lu, X.; Zhu, C.; Peng, H.; Johnson, P. A.; et al. Joule 2019, 3, 1140. doi: 10.1016/j.joule.2019.01.004
24. [24]
  Che, X.; Li, Y.; Qu, Y.; Forrest, S. R. Nat. Energy 2018, 3, 422. doi: 10.1038/s41560-018-0134-z doi: 10.1038/s41560-018-0134-z
25. [25]
  Bin, H.; Gao, L.; Zhang, Z. G.; Yang, Y.; Zhang, Y.; Zhang, C.; Chen, S.; Xue, L.; Yang, C.; Xiao, M.; et al. Nat. Commun. 2016, 7, 13651. doi: 10.1038/ncomms13651
26. [26]
  Meng, L.; Zhang, Y.; Wan, X.; Li, C.; Zhang, X.; Wang, Y.; Ke, X.; Xiao, Z.; Ding, L.; Xia, R.; et al. Science 2018, 361, 1094. doi: 10.1126/science.aat2612
27. [27]
  Cui, Y.; Yao, H.; Hong, L.; Zhang, T.; Xu, Y.; Xian, K.; Gao, B.; Qin, J.; Zhang, J.; Wei, Z.; et al. Adv. Mater. 2019, 0, 1808356. doi: 10.1002/adma.201808356
28. [28]
  Duan, C.; Cai, W.; Hsu, B. B. Y.; Zhong, C.; Zhang, K.; Liu, C.; Hu, Z.; Huang, F.; Bazan, G. C.; Heeger, A. J.; et al. Energy Environ. Sci. 2013, 6, 3022. doi: 10.1039/C3EE41838C
29. [29]
  Xu, X.; Yu, T.; Bi, Z.; Ma, W.; Li, Y.; Peng, Q. Adv. Mater. 2018, 30, 1703973. doi: 10.1002/adma.201703973 doi: 10.1002/adma.201703973
30. [30]
  Fan, B.; Ying, L.; Wang, Z.; He, B.; Jiang, X. F.; Huang, F.; Cao, Y. Energy Environ. Sci. 2017, 10, 1243. doi: 10.1039/C7EE00619E doi: 10.1039/C7EE00619E
31. [31]
  Li, Z.; Ying, L.; Zhu, P.; Zhong, W.; Li, N.; Liu, F.; Huang, F.; Cao, Y. Energy Environ. Sci. 2019, 12, 157. doi: 10.1039/C8EE02863J doi: 10.1039/C8EE02863J
32. [32]
  Zhang, S.; Ye, L.; Zhang, H.; Hou, J. Mater. Today 2016, 19, 533. doi: 10.1016/j.mattod.2016.02.019 doi: 10.1016/j.mattod.2016.02.019
33. [33]
  Chen, Y.; Zhang, S.; Wu, Y.; Hou, J. Adv. Mater. 2014, 26, 2744. doi: 10.1002/adma.201304825 doi: 10.1002/adma.201304825
34. [34]
  Hou, J.; Inganäs, O.; Friend, R. H.; Gao, F. Nat. Mater. 2018, 17, 119. doi: 10.1038/nmat5063 doi: 10.1038/nmat5063
35. [35]
  Fan, Q.; Zhu, Q.; Xu, Z.; Su, W.; Chen, J.; Wu, J.; Guo, X.; Ma, W.; Zhang, M.; Li, Y. Nano Energy 2018, 48, 413. doi: 10.1016/j.nanoen.2018.04.002 doi: 10.1016/j.nanoen.2018.04.002
36. [36]
  Fan, Q.; Su, W.; Guo, X.; Guo, B.; Li, W.; Zhang, Y.; Wang, K.; Zhang, M.; Li, Y. Adv. Energy Mater. 2016, 6, 1600430. doi: 10.1002/aenm.201600430 doi: 10.1002/aenm.201600430
37. [37]
  Yu, R.; Zhang, S.; Yao, H.; Guo, B.; Li, S.; Zhang, H.; Zhang, M.; Hou, J. Adv. Mater. 2017, 29, 1700437. doi: 10.1002/adma.201700437 doi: 10.1002/adma.201700437
38. [38]
  Huang, F.; Wu, H.; Wang, D.; Yang, W.; Cao, Y. Chem. Mater. 2004, 16, 708.doi: 10.1021/cm034650o doi: 10.1021/cm034650o
39. [39]
  Yang, T. B.; Wang, M.; Duan, C. H.; Hu, X. W.; Huang, L.; Peng, J. B.; Huang, F.; Gong, X. Energy Environ. Sci. 2012, 5, 8208. doi: 10.1039/C2ee22296e doi: 10.1039/C2ee22296e
40. [40]
  Li, W.; Zhang, S.; Zhang, H.; Hou, J. Org. Electron. 2017, 44, 42. doi: 10.1016/j.orgel.2017.01.036 doi: 10.1016/j.orgel.2017.01.036
41. [41]
  Zhang, J.; Tan, H. S.; Guo, X.; Facchetti, A.; Yan, H. Nat. Energy 2018, 3, 720. doi: 10.1038/s41560-018-0181-5 doi: 10.1038/s41560-018-0181-5
42. [42]
  Zhao, W.; Qian, D.; Zhang, S.; Li, S.; Inganas, O.; Gao, F.; Hou, J. Adv. Mater. 2016, 28, 4734. doi: 10.1002/adma.201600281 doi: 10.1002/adma.201600281
43. [43]
  Zhang, S.; Hou, J. Acta Phys. -Chim. Sin. 2017, 33, 2327. doi: 10.3866/PKU.WHXB201706161
44. [44]
  Xu, Y.; Yao, H.; Hou, J. Chin. J. Chem. 2019, 37, 207. doi: 10.1002/cjoc.201800471 doi: 10.1002/cjoc.201800471
45. [45]
  Zhang, S.; Ye, L.; Wang, Q.; Li, Z.; Guo, X.; Huo, L.; Fan, H.; Hou, J. J. Phys. Chem. C 2013, 117, 9550. doi: 10.1021/jp312450p doi: 10.1021/jp312450p
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