Citation: DENG Dan, ZHOU Erjun, WEI Zhixiang. Fluorination: An Effective Molecular Design Strategy for Efficient Photovoltaic Materials[J]. Acta Physico-Chimica Sinica, ;2018, 34(11): 1239-1249. doi: 10.3866/PKU.WHXB201803272 shu

Fluorination: An Effective Molecular Design Strategy for Efficient Photovoltaic Materials

National Center for Nanoscience and Technology, Beijing 100190, P. R. China

Corresponding author: ZHOU Erjun, zhouej@nanoctr.cn WEI Zhixiang, weizx@nanoctr.cn
Received Date: 23 February 2018
Revised Date: 22 March 2018
Accepted Date: 23 March 2018
Available Online: 27 November 2018
Fund Project: The project was supported by the National Natural Science Foundation of China (51603051, 21125420) and the Youth Innovation Promotion Association CASthe National Natural Science Foundation of China 21125420the National Natural Science Foundation of China 21125420

Organic solar cells (OSCs) have received widespread attention for their advantages of cheap, light, flexible characteristics and roll-to-roll printing technology. However, the efficiencies of OSCs are still lower than 50% of the theoretical Shockley-Queisser detailed-balance efficiency limit. Consequently, to further improve device performance, it is significant to develop molecular design strategies to lower the energy loss and enhance the utilization of absorbed photons. From the molecular design aspects, down-shifting energy levels is an effective way to lowering the energy loss in order to obtain a high open circuit voltage, and optimizing the morphology is an efficient approach to lowering the fill factor and current density loss. Introduction of fluorine atom in molecules is an effective molecular design strategy to realize both above-mentioned requirements. In this review, starting from the characteristics of fluorine atoms, we summarized the fluorination effects on adjusting molecular levels. Whether the fluorine attached to the donor units, acceptor units or π-bridge units, it could efficiently downshift the energy levels. However, fluorinating the molecular backbone affects the energy levels more significantly than fluorinating the side chains of the two-dimensional structures. The introduction of fluorine is also an effective approach to optimize molecular packing and morphology. Generally, whether the fluorine attached to the donor units, acceptor units or π-bridge units, it can effectively increase molecular coherence length, decrease π–π stacking distance, and enhance domain purity. However, there is a saturation of the fluorine on the backbone, further introduction of the fluorine can accelerate molecular aggregation and induce disorder. In addition, the position of fluorination is important. In this review, we also briefly discuss the fluorination strategy for representative and high-efficiency photovoltaic material designs, including small molecule, polymer, and non-fullerene OSCs, mainly focusing on improving efficiency by reducing the efficiency losses. Fluorination is advantageous only for OSCs with high HOMO energy levels or poor molecular packing; otherwise, it can compromise device performance. OSCs based on narrow band-gap non-fullerene acceptors with low energy loss show promise for highly efficient device performance. Fluorination provides an effective means to fine-tune energy levels and form ideal microstructures to further reduce the efficiency loss and achieve a breakthrough in device performance.
- Fluorination,
- Energy level,
- Morphology,
- Energy loss,
- Power conversion efficiency
1. [1]
  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
2. [2]
  Li, Y. Acc. Chem. Res. 2012, 45(5), 723. doi: 10.1021/ar2002446 doi: 10.1021/ar2002446
3. [3]
  Coughlin, J. E.; Henson, Z. B.; Welch, G. C.; Bazan, G. C. Acc. Chem. Res. 2014, 47(1), 257. doi: 10.1021/ar400136b doi: 10.1021/ar400136b
4. [4]
  Chen, J.; Cao, Y. Acc. Chem. Res. 2009, 42(11), 1709. doi: 10.1021/ar900061z doi: 10.1021/ar900061z
5. [5]
  Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Nat. Mater. 2012, 11(1), 44. doi: 10.1038/nmat3160 doi: 10.1038/nmat3160
6. [6]
  Roncali, J. Acc. Chem. Res. 2009, 42(11), 1719. doi: 10.1021/ar900041b doi: 10.1021/ar900041b
7. [7]
  Zhang, J.; Deng, D.; He, C.; He, Y.; Zhang, M.; Zhang, Z. G.; Zhang, Z.; Li, Y. Chem. Mater. 2010, 23(3), 817. doi: 10.1021/cm102077j doi: 10.1021/cm102077j
8. [8]
  Zhao, W.; Li, S.; Yao, H.; Zhang, S.; Zhang, Y.; Yang, B.; Hou, J. J. Am. Chem. Soc. 2017, 139(21), 7148. doi: 10.1021/jacs.7b02677 doi: 10.1021/jacs.7b02677
9. [9]
  Yang, L.; Zhang, S.; He, C.; Zhang, J.; Yao, H.; Yang, Y.; Zhang, Y.; Zhao, W.; Hou, J. J. Am. Chem. Soc. 2017, 139(5), 1958. doi: 10.1021/jacs.6b11612 doi: 10.1021/jacs.6b11612
10. [10]
  Lin, Y.; Wang, J.; Zhang, Z. G.; Bai, H.; Li, Y.; Zhu, D.; Zhan, X. Adv. Mater. 2015, 27(7), 1170. doi: 10.1002/adma.201404317 doi: 10.1002/adma.201404317
11. [11]
  Yang, Y.; Zhang, Z. G.; Bin, H.; Chen, S.; Gao, L.; Xue, L.; Yang, C.; Li, Y. J. Am. Chem. Soc. 2016, 138(45), 15011. doi: 10.1021/jacs.6b09110 doi: 10.1021/jacs.6b09110
12. [12]
  Hou, J.; Inganäs, O.; Friend, R. H.; Gao, F. Nat. Mater. 2018, 17, 119. doi: 10.1038/nmat5063 doi: 10.1038/nmat5063
13. [13]
  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 doi: 10.1038/ncomms13740
14. [14]
  Wan, J.; Xu, X.; Zhang, G.; Li, Y.; Feng, K.; Peng, Q. Energy Envirn. Sci. 2017, 10 (8), 1739. doi: 10.1039/C7EE00805H doi: 10.1039/C7EE00805H
15. [15]
  Polman, A.; Knight, M.; Garnett, E. C.; Ehrler, B.; Sinke, W. C. Science 2016, 352(6283). doi: 10.1126/science.aad4424 doi: 10.1126/science.aad4424
16. [16]
  Kawashima, K.; Tamai, Y.; Ohkita, H.; Osaka, I.; Takimiya, K. Nat. Commun. 2015, 6, 10085. doi: 10.1038/ncomms10085 doi: 10.1038/ncomms10085
17. [17]
  Zhang, J.; Zhu, L.; Wei, Z. Small Methods 2017, 1(12), 1700258. doi: 10.1002/smtd.201700258 doi: 10.1002/smtd.201700258
18. [18]
  Liu, J.; Chen, S.; Qian, D.; Gautam, B.; Yang, G.; Zhao, J.; Bergqvist, J.; Zhang, F.; Ma, W.; Ade, H.; et al. Nat. Energy 2016, 1, 16089. doi: 10.1038/nenergy.2016.89 doi: 10.1038/nenergy.2016.89
19. [19]
  Li, W.; Roelofs, W. S. C.; Wienk, M. M.; Janssen, R. A. J. J. Am. Chem. Soc. 2012, 134(33), 13787. doi: 10.1021/ja305358z doi: 10.1021/ja305358z
20. [20]
  Bin, H.; Zhang, Z. G.; Gao, L.; Chen, S.; Zhong, L.; Xue, L.; Yang, C.; Li, Y. J. Am. Chem. Soc. 2016, 138(13), 4657. doi: 10.1021/jacs.6b01744 doi: 10.1021/jacs.6b01744
21. [21]
  Zheng, Z.; Awartani, O. M.; Gautam, B.; Liu, D.; Qin, Y.; Li, W.; Bataller, A.; Gundogdu, K.; Ade, H.; Hou, J. Adv. Mater. 2017, 29(5), 1604241. doi: 10.1002/adma.201604241 doi: 10.1002/adma.201604241
22. [22]
  Xu, X. P.; Li, Y.; Luo, M. M.; Peng, Q. Chin. Chem. Lett. 2016, 27(8), 1241. doi: 10.1016/j.cclet.2016.05.006 doi: 10.1016/j.cclet.2016.05.006
23. [23]
  Meyer, F. Prog. Polym. Sci. 2015, 47, 70. doi: 10.1016/j.progpolymsci.2015.04.007 doi: 10.1016/j.progpolymsci.2015.04.007
24. [24]
  Zhang, Q.; Kelly, M. A.; Bauer, N.; You, W. Acc. Chem. Res. 2017, 50(9), 2401. doi: 10.1021/acs.accounts.7b00326 doi: 10.1021/acs.accounts.7b00326
25. [25]
  Kohlhepp, S. V.; Gulder, T. Chem. Soc. Rev. 2016, 45(22), 6270. doi: 10.1039/C6CS00361C doi: 10.1039/C6CS00361C
26. [26]
  Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107(4), 1296. doi: 10.1021/cr0501543 doi: 10.1021/cr0501543
27. [27]
  Delgado, M. C. R.; Pigg, K. R.; da Silva Filho, D. A.; Gruhn, N. E.; Sakamoto, Y.; Suzuki, T.; Osuna, R. M.; Casado, J.; Hernández, V.; Navarrete, J. T. L.; et al. J. Am. Chem. Soc. 2009, 131(4), 1502. doi: 10.1021/ja807528w doi: 10.1021/ja807528w
28. [28]
  Tang, M. L.; Reichardt, A. D.; Wei, P.; Bao, Z. J. Am. Chem. Soc. 2009, 131(14), 5264. doi: 10.1021/ja809659b doi: 10.1021/ja809659b
29. [29]
  Gao, Y.; Deng, Y.; Tian, H.; Zhang, J.; Yan, D.; Geng, Y.; Wang, F. Adv. Mater. 2017, 29(13), 1606217. doi: 10.1002/adma.201606217 doi: 10.1002/adma.201606217
30. [30]
  Chen, H. Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang, Y.; Yu, L.; Wu, Y.; Li, G. Nat. Photon. 2009, 3, 649. doi: 10.1038/nphoton.2009.192 doi: 10.1038/nphoton.2009.192
31. [31]
  Rolczynski, B. S.; Szarko, J. M.; Son, H. J.; Liang, Y.; Yu, L.; Chen, L. X. J. Am. Chem. Soc. 2012, 134(9), 4142. doi: 10.1021/ja209003y. doi: 10.1021/ja209003y
32. [32]
  Son, H. J.; Wang, W.; Xu, T.; Liang, Y.; Wu, Y.; Li, G.; Yu, L. J. Am. Chem. Soc. 2011, 133(6), 1885. doi: 10.1021/ja108601g doi: 10.1021/ja108601g
33. [33]
  Zhang, M.; Guo, X.; Zhang, S.; Hou, J. Adv. Mater. 2014, 26(7), 1118. doi: 10.1002/adma.201304427 doi: 10.1002/adma.201304427
34. [34]
  Wang, Z.; Xu, X.; Li, Z.; Feng, K.; Li, K.; Li, Y.; Peng, Q. Adv. Electron Mater. 2016, 2 (6), 1600061. doi: 10.1002/aelm.201600061 doi: 10.1002/aelm.201600061
35. [35]
  Jackson, N. E.; Savoie, B. M.; Kohlstedt, K. L.; Olvera de la Cruz, M.; Schatz, G. C.; Chen, L. X.; Ratner, M. A. J. Am. Chem. Soc. 2013, 135(28), doi: 10475. 10.1021/ja403667s
36. [36]
  Takacs, C. J.; Sun, Y.; Welch, G. C.; Perez, L. A.; Liu, X.; Wen, W.; Bazan, G. C.; Heeger, A. J. J. Am. Chem. Soc. 2012, 134 (40), 16597. doi: 10.1021/ja3050713 doi: 10.1021/ja3050713
37. [37]
  van der Poll, T. S.; Love, J. A.; Nguyen, T. Q.; Bazan, G. C. Adv. Mater. 2012, 24(27), 3646. doi: 10.1002/adma.201201127 doi: 10.1002/adma.201201127
38. [38]
  Ying, L.; Hsu, B. B. Y.; Zhan, H.; Welch, G. C.; Zalar, P.; Perez, L. A.; Kramer, E. J.; Nguyen, T. Q.; Heeger, A. J.; Wong, W. Y.; et al. J. Am. Chem. Soc. 2011, 133(46), 18538. doi: 10.1021/ja207543g doi: 10.1021/ja207543g
39. [39]
  Price, S. C.; Stuart, A. C.; Yang, L.; Zhou, H.; You, W. J. Am. Chem. Soc. 2011, 133 (12), 4625. doi: 10.1021/ja1112595 doi: 10.1021/ja1112595
40. [40]
  Li, W.; Albrecht, S.; Yang, L.; Roland, S.; Tumbleston, J. R.; McAfee, T.; Yan, L.; Kelly, M. A.; Ade, H.; Neher, D.; et al. J. Am. Chem. Soc. 2014, 136(44), 15566. doi: 10.1021/ja5067724 doi: 10.1021/ja5067724
41. [41]
  Stuart, A. C.; Tumbleston, J. R.; Zhou, H.; Li, W.; Liu, S.; Ade, H.; You, W. J. Am. Chem. Soc. 2013, 135(5), 1806. doi: 10.1021/ja309289u doi: 10.1021/ja309289u
42. [42]
  Kim, J. H.; Song, C. E.; Kim, H. U.; Grimsdale, A. C.; Moon, S. J.; Shin, W. S.; Choi, S. K.; Hwang, D. H. Chem. Mater. 2013, 25(13), 2722. doi: 10.1021/cm401527b doi: 10.1021/cm401527b
43. [43]
  Kawashima, K.; Fukuhara, T.; Suda, Y.; Suzuki, Y.; Koganezawa, T.; Yoshida, H.; Ohkita, H.; Osaka, I.; Takimiya, K. J. Am. Chem. Soc. 2016, 138 (32), 10265. doi: 10.1021/jacs.6b05418 doi: 10.1021/jacs.6b05418
44. [44]
  Uddin, M. A.; Kim, Y.; Younts, R.; Lee, W.; Gautam, B.; Choi, J.; Wang, C.; Gundogdu, K.; Kim, B. J.; Woo, H. Y. Macromolecules 2016, 49 (17), 6374. doi: 10.1021/acs.macromol.6b01414 doi: 10.1021/acs.macromol.6b01414
45. [45]
  Zhang, Y.; Deng, D.; Wang, Z.; Wang, Y.; Zhang, J.; Fang, J.; Yang, Y.; Lu, G.; Ma, W.; Wei, Z. Adv. Energy Mater. 2017, 7(22), 1701548. doi: 10.1002/aenm.201701548 doi: 10.1002/aenm.201701548
46. [46]
  Dai, S.; Zhao, F.; Zhang, Q.; Lau, T. K.; Li, T.; Liu, K.; Ling, Q.; Wang, C.; Lu, X.; You, W.; Zhan, X. J. Am. Chem. Soc. 2017, 139(3), 1336. doi: 10.1021/jacs.6b12755 doi: 10.1021/jacs.6b12755
47. [47]
  Yao, H.; Cui, Y.; Yu, R.; Gao, B.; Zhang, H.; Hou, J. Angew. Chem. Int. Ed. 2017, 56(11), 3045. doi:10.1002/anie.201610944 doi: 10.1002/anie.201610944
48. [48]
  Ma, X.; Mi, Y.; Zhang, F.; An, Q.; Zhang, M.; Hu, Z.; Liu, X.; Zhang, J.; Tang, W. Adv. Energy Mater. 2018, 8 (1), 1702854. doi: 10.1002/aenm.201702854 doi: 10.1002/aenm.201702854
1. [1]
  Qin ZHU , Jiao MA , Zhihui QIAN , Yuxu LUO , Yujiao GUO , Mingwu XIANG , Xiaofang LIU , Ping NING , Junming GUO . Morphological evolution and electrochemical properties of cathode material LiAl_0.08Mn_1.92O₄ single crystal particles. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1549-1562. doi: 10.11862/CJIC.20240022
2. [2]
  Juan Yuan , Bin Zhang , Jinping Wu , Mengfan Wang . Design of a Comprehensive Experiment on Preparation and Characterization of Cu₂(Salen)₂ Nanomaterials with Two Distinct Morphologies. University Chemistry, 2024, 39(10): 420-425. doi: 10.3866/PKU.DXHX202402014
3. [3]
  Yanhui XUE , Shaofei CHAO , Man XU , Qiong WU , Fufa WU , Sufyan Javed Muhammad . Construction of high energy density hexagonal hole MXene aqueous supercapacitor by vacancy defect control strategy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1640-1652. doi: 10.11862/CJIC.20240183
4. [4]
  Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
5. [5]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
6. [6]
  Xin XIONG , Qian CHEN , Quan XIE . First principles study of the photoelectric properties and magnetism of La and Yb doped AlN. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1519-1527. doi: 10.11862/CJIC.20240064
7. [7]
  Xinyuan Shi , Chenyangjiang , Changyu Zhai , Xuemei Lu , Jia Li , Zhu Mao . Preparation and Photoelectric Performance Characterization of Perovskite CsPbBr₃ Thin Films. University Chemistry, 2024, 39(6): 383-389. doi: 10.3866/PKU.DXHX202312019
8. [8]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
9. [9]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(759)
HTML views(103)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142