Research Progress on Small-Molecule Photovoltaic Materials Based on Donor-Acceptor-Donor Type Polycyclic Aromatic Hydrocarbons

doi:10.6023/cjoc202005023

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4031-4045.DOI: 10.6023/cjoc202005023 Previous Articles Next Articles

基于给体-受体-给体型稠环模块的小分子光伏材料的研究进展

戴学新^a,b, 成晓东^a, 阚志鹏^b, 肖泽云^b, 段泰男^b, 胡超^b, 陆仕荣^b

a 黔南民族师范学院化学化工学院贵州都匀 558000;
b 中国科学院重庆绿色智能技术研究院有机半导体研究中心重庆 400714

收稿日期:2020-05-10 修回日期:2020-07-28 发布日期:2020-09-16
通讯作者: 戴学新, 胡超, 陆仕荣 E-mail:daixuexin@sgmtu.edu.cn;huchao@cigit.ac.cn;lushirong@cigit.ac.cn
基金资助:
国家自然科学基金（No.21762036）、贵州省科技厅（No.LH[2015]7706）和贵州省教育厅（No.KY[2018]422）资助项目.

Research Progress on Small-Molecule Photovoltaic Materials Based on Donor-Acceptor-Donor Type Polycyclic Aromatic Hydrocarbons

Dai Xuexin^a,b, Cheng Xiaodong^a, Kan Zhipeng^b, Xiao Zeyun^b, Duan Tainan^b, Hu Chao^b, Lu Shirong^b

a School of Chemistry and Chemical Engineering, Qiannan Normal University for Nationalities, Duyun, Guizhou 558000;
b Organic Semiconductor Research Center, Chongqing Institute of Green and Intelligent Technology, Chinese Academy of Science, Chongqing 400714

Received:2020-05-10 Revised:2020-07-28 Published:2020-09-16
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21762036), the Science and Technology Foundation of Guizhou Province (No. LH[2015]7706) and the Education Department of Guizhou Province (No. KY[2018]422).

Donor-acceptor-donor (D-A-D) type polycyclic aromatic hydrocarbon and its derivatives have been widely used in the design of photovoltaic materials and have made great breakthrough in recent years, due to their advantages of unique large planar structure, high charge mobility, excellent light absorption performance, thermal and light stability. The latest research progress of small-molecule photovoltaic materials based on D-A-D type polycyclic aromatic hydrocarbons is reviewed. The relationships between photovoltaic properties and the molecular structures are analyzed systematically.

Key words: polycyclic aromatic hydrocarbon, solar cell, small-molecule, organic photovoltaic material

Cite this article

Dai Xuexin, Cheng Xiaodong, Kan Zhipeng, Xiao Zeyun, Duan Tainan, Hu Chao, Lu Shirong. Research Progress on Small-Molecule Photovoltaic Materials Based on Donor-Acceptor-Donor Type Polycyclic Aromatic Hydrocarbons[J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4031-4045.

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[1] Wang, Y.; Michinobu, T. J. Mater. Chem. C 2016, 4, 6200.
[2] Geng, Y.; Tang, A.; Tajima, K.; Zeng, Q.; Zhou, E. J. Mater. Chem. A 2019, 7, 64.
[3] Godfroy, M.; Aumaitre, C.; Caffy, F.; Kervella, Y.; Cabau, L.; Pellejà, L.; Maldivi, P.; Narbey, S.; Oswald, F.; Palomares, E.; Joly, D.; Demadrille, R. Dyes Pigm. 2017, 146, 352.
[4] Cui, Y.; Yao, H.; Zhang, J.; Xian, K.; Zhang, T.; Hong, L.; Wang, Y.; Xu, Y.; Ma, K.; An, C.; He, C.; Wei, Z.; Gao, F.; Hou, J. Adv. Mater. 2020, 32, 1908205.
[5] Wang, Y.; Chen, W.; Wang, L.; Tu, B.; Chen, T.; Liu, B.; Yang, K.; Koh, C.; Zhang, X.; Sun, H.; Chen, G.; Feng, X.; Woo, H.; Djurišić, A.; He, Z.; Guo, X. Adv. Mater. 2019, 31, 1902781.
[6] Cheng, Y.; Chen, C.; Ho, Y.; Chang, S.; Witek, H.; Hsu, C. Org. Lett. 2011, 13, 5484.
[7] Arroyave, F.; Richard, C.; Reynolds, J. Org. Lett. 2012, 14, 6138.
[8] O'Regan, B.; Grätzel, M. Nature 1991, 353, 737.
[9] Grätzel, M. Nature 2001, 414, 338.
[10] Grätzel, M. Acc. Chem. Res. 2009, 42, 1788.
[11] Ooyama, Y.; Harima, Y. ChemPhysChem 2012, 13, 4032.
[12] Qu, S.; Hua, J.; Tian, H. Sci. China:Chem. 2012, 42, 567.
[13] Luo, J.; Wan, Z.; Jia, C. Chin. Chem. Lett. 2016, 27, 1304.
[14] Huang, Z; Meier, H.; Cao, D. J. Mater. Chem. C 2016, 4, 2404.
[15] Tian, Y.; Cai, N.; Chen, Y.; Qian, S.; Huo, Y. Chin. J. Org. Chem. 2018, 38, 1085(in Chinese). (田亚娟, 蔡宁, 陈亚通, 钱赛男, 霍延平, 有机化学, 2018, 38, 1085.)
[16] Huang, Z.; Feng, H.; Zang X.; Iqbal, Z.; Zeng, H.; Kuang, D.; Wang, L.; Meier, H.; Cao, D. J. Mater. Chem. A 2014, 2, 15365.
[17] Huang, Z.; Hua, T.; Tian, J.; Wang, L.; Meier, H.; Cao, D. Dyes Pigm. 2016, 125, 229.
[18] Ni, J.; You, J.; Hung, W.; Kao, W.; Chou, H.; Lin, J. ACS Appl. Mater. Int. 2014, 6, 22612.
[19] Richard, C.; Pan, Z.; Hsu, H.; Cekli, S.; Schanze, K.; Reynolds, J. ACS Appl. Mater. Int. 2014, 6, 5221.
[20] Richard, C.; Pan, Z.; Parthasarathy, A.; Arroyave, F.; Estrada, L.; Schanzeb, K.; Reynolds, J. J. Mater. Chem. A 2014, 2, 9866.
[21] Huang, Z.; Zang, X.; Hua, T.; Wang, L.; Meier, H.; Cao, D. ACS Appl. Mater. Interfaces 2015, 7, 20418.
[22] Ni, J.; Kao, W.; Chou, H.; Lin, J. ChemSusChem 2015, 8, 2932.
[23] Ni, J.; Chiu, T.; Kao, W.; Chou, H.; Su, C.; Lin, J. ACS Appl. Mater. Int. 2016, 8, 23066.
[24] Lin, Y.; Zhan, X. Adv. Energy Mater. 2015, 5, 1501063.
[25] Dai, S.; Zhan, X. Acta Polym. Sinica 2017, 1706(in Chinese). (代水星, 占肖卫, 高分子学报, 2017, 1706.)
[26] Lin, Y.; Wang, J.; Zhang, Z.; Bai, H.; Li, Y.; Zhu, D.; Zhan, X. Adv. Mater. 2015, 27, 1170.
[27] Yan, C.; Barlow, S.; Wang, Z.; Yan, H.; Jen, A.; Marder, S.; Zhan, X. Nat. Rev. Mater. 2018, 3, 18003.
[28] Lin, Y.; Li, Y.; Zhan, X. Chem. Soc. Rev. 2012, 41, 4245.
[29] Lin, Y.; Zhan, X. Acc. Chem. Res. 2016, 49, 175.
[30] Lin, Y.; Zhang, Z.; Bai, H.; Wang, J.; Yao, Y.; Li, Y.; Zhu, D.; Zhan, X. Energy Environ. Sci. 2015, 8, 610.
[31] Yuan, J.; Huang, T.; Cheng, P.; Zou, Y.; Zhang, H.; Yang, J.; Chang, S.; Zhang, Z.; Huang, W.; Wang, R.; Meng, D.; Gao, F.; Yang, Y. Nat. Commun. 2019, 10, 570.
[32] Feng, L.; Yuan J.; Zhang, Z.; Peng, H.; Zhang, Z.; Xu, S.; Liu, Y.; Li, Y.; Zou, Y. ACS Appl. Mater. Interfaces 2017, 9, 31985.
[33] Luo, M.; Zhou, L.; Yuan, J.; Zhu C.; Cai, F.; Hai, J.; Zou, Y. J. Energy Chem. 2020, 42, 169.
[34] Ma, X.; Luo, M.; Gao, W.; Yuan, J.; An, Q.; Zhang, M.; Hu, Z.; Gao, J.; Wang, J.; Zou, Y.; Yang, C.; Zhang, F. J. Mater. Chem. A 2019, 7, 7843.
[35] Dai, S.; Zhao, F.; Zhang, Q.; Lau, T.; Li, T.; Liu, K.; Ling, Q.; Wang, C.; Lu, X.; You, W.; Zhan, X. J. Am. Chem. Soc. 2017, 139, 1336.
[36] Luo, M.; Zhu, C.; Yuan, J.; Zhou, L.; Keshtov, M.; Godovsky, D.; Zou, Y. Chin. Chem. Lett. 2019, 30, 2343.
[37] Liu, S.; Yuan, J.; Deng, W.; Luo, M.; Xie, Y.; Liang, Q.; Zou, Y.; He, Z.; Wu, H.; Cao, Y. Nat. Photonics 2020, 14, 300.
[38] Yuan, J.; Zhang, Y.; Zhou, L.; Zhang, C.; Lau, T.; Zhang, G.; Lu, X.; Yip, H.; So, S.; Beaupré, S.; Mainville, M.; Johnson, P.; Leclerc, M.; Chen, H.; Peng, H.; Li, Y.; Zou, Y. Adv. Mater. 2019, 31, 1807577.
[39] Yuan, J.; Zhang, Y.; Zhou, L.; Zhang, G.; Yip, H.; Lau, T.; Lu, X.; Zhu, C.; Peng, H.; Johnson, P.; Leclerc, M.; Cao, Y.; Ulanski, J.; Li, Y.; Zou, Y. Joule 2019, 3, 1140.
[40] Chen, H.; Hu, D.; Yang, Q.; Gao, J.; Fu, J.; Yang, K.; He, H.; Chen, S.; Kan, Z.; Duan, T.; Yang, C.; Ouyang, J.; Xiao, Z.; Sun, K.; Lu, S. Joule 2019, 3, 3034.
[41] Yue, Q.; Wu, H.; Zhou, Z.; Zhang, M.; Liu, F.; Zhu, X. Adv. Mater. 2019, 31, 1904283.
[42] Fan, B.; Zhang, D.; Li, M.; Zhong, W.; Zeng, Z.; Ying, L.; Huang, F.; Cao, Y. Sci. China:Chem. 2019, 62, 746.
[43] Cui, Y.; Yao, H.; Zhang, J.; Zhang, T.; Wang, Y.; Hong, L.; Xian, K.; Xu, B.; Zhang, S.; Peng, J.; Wei, Z.; Gao, F.; Hou, J. Nat. Commun. 2019, 10, 2515.
[44] Wang, H.; Liu, T.; Zhou, J.; Mo, D.; Han, L.; Lai, H.; Chen, H.; Zheng, N.; Zhu, Y.; Xie, Z.; He, F. Adv. Sci. 2020, 7, 1903784.
[45] Xu, X.; Feng, K.; Lee, Y.; Woo, H.; Zhang, G.; Peng, Q. Adv. Funct. Mater. 2020, 30, 1907570.
[46] Li, X.; Pan, M.; Lau, T.; Liu, W.; Li, K.; Yao, N.; Shen, F.; Huo, S.; Zhang, F.; Wu, Y.; Li, X.; Lu, X.; Yan, H.; Zhan, C. Chem. Mater. 2020, 32, 5182.
[47] Jiang, K.; Wei, Q.; Lai, J.; Peng, Z.; Kim, H.; Yuan, J.; Ye, L.; Ade, H.; Zou, Y.; Yan, H. Joule 2019, 3, 3020.
[48] Luo, Z.; Sun, R.; Zhong, C.; Liu, T.; Zhang, G.; Zou, Y.; Jiao, X.; Min, J.; Yang, C. Sci. China:Chem. 2020, 63, 361.
[49] Cui, Y.; Yao, H.; Hong, L.; Zhang, T.; Tang, Y.; Lin, B.; Xian, K.; Gao, B.; An, C.; Bi, P.; Ma, W.; Hou, J. Nat. Sci. Rev. 2019, nwz200.
[50] Chai, G.; Chang, Y.; Peng, Z.; Jia, Y.; Zou, X.; Yu, D.; Yu, H.; Chen, Y.; Chow, P.; Wong, K.; Zhang, J.; Ade, H.; Yang, L.; Zhan, C. Nano Energy 2020, 76, 105087.
[51] Zhou, Z.; Liu, W.; Zhou, G.; Zhang, M.; Qian, D.; Zhang, J.; Chen, S.; Xu, S.; Yang, C.; Gao, F.; Zhu, H.; Liu, F.; Zhu, X. Adv. Mater. 2020, 32, 1906324.
[52] Gao, J.; Gao, W.; Ma, X.; Hu, Z.; Xu, C.; Wang, X.; An, Q.; Yang, C.; Zhang, X.; Zhang, F. Energy Environ. Sci. 2020, 13, 958.
[53] Lai, H.; Chen, H.; Zhu, Y.; Chen, L.; Huang, H.; He, F. J. Mater. Chem. A 2020, 8, 96706.
[54] Luo, Z.; Ma, R.; Liu, T.; Yu, J.; Xiao, Y.; Sun, R.; Xie, G.; Yuan, Y.; Chen, Y.; Chen, K.; Chai, G.; Sun, H; Min, J.; Zhang, J.; Zou, Y.; Yang, C.; Lu, X.; Gao, F.; Yan, H. Joule 2020, 4, 1236.
[55] Sun, C.; Qin, S.; Wang, R.; Chen, S.; Pan, F.; Qiu, B.; Shang, Z.; Meng, L.; Zhang, C.; Xiao, M.; Yang, C.; Li, Y. J. Am. Chem. Soc. 2020, 142, 1465.
[56] Yang, C.; Zhang, S.; Ren, J.; Gao, M.; Bi, P.; Ye, L.; Hou, J. Energy Environ. Sci. 2020, 13, 2864.
[57] Best Research-Cell Efficiency Chart,[2020-03-11] https://www.nrel.gov/pv/cell-efficiency.html.
[58] Zhao, X.; Quan, Y.; Pan, H.; Li, Q.; Shen, Y.; Huang, Z.; Wang, M. J. Energy Chem. 2019, 32, 85.
[59] Ye, X.; Zhao, X.; Li, Q.; Ma, Y.; Song, W.; Quan, Y.; Wang, Z.; Wang, M.; Huang, Z. Dyes Pigm. 2019, 164, 407.
[60] Tu, B.; Wang, Y.; Chen, W.; Liu, B.; Feng, X.; Zhu, Y.; Yang, K.; Zhang, Z.; Shi, Y.; Guo, X.; Li, H.; Tang, Z.; Djurišić, A.; He, Z. ACS Appl. Mater. Interfaces 2019, 11, 48556.

基于给体-受体-给体型稠环模块的小分子光伏材料的研究进展

Research Progress on Small-Molecule Photovoltaic Materials Based on Donor-Acceptor-Donor Type Polycyclic Aromatic Hydrocarbons

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