Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution

doi:10.6023/cjoc201808034

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 157-169.DOI: 10.6023/cjoc201808034 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Articles

苯并二噻吩/苯并噻二唑ADA型光电化合物:氟取代的影响

梁龙^a,b, 刘丽娜^b, 陈学强^b, 项宣^b, 凌君^c, 鲁郑全^a, 李靖靖^a, 李维实^a,b

a 郑州工程技术学院郑州高性能有机材料工程研究中心郑州 450044;
b 中国科学院上海有机化学研究所有机功能分子合成与组装重点实验室上海 200032;
c 浙江大学高分子科学与工程学系杭州 320027

收稿日期:2018-08-28 修回日期:2018-10-25 发布日期:2018-11-12
通讯作者: 李维实 E-mail:liws@mail.sioc.ac.cn
基金资助:
国家自然科学基金（Nos.21474129，21674125，51761145043）、中国科学院先导项目（No.XDB20020000）、河南省科技开放合作项目（Nos.162106000018和172106000067）和郑州技术工程学院资助项目.

Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution

Liang Long^a,b, Liu Li-Na^b, Chen Xue-Qiang^b, Xiang Xuan^b, Ling Jun^c, Lu Zheng-Quan^a, Li Jing-Jing^a, Li Wei-Shi^a,b

a Zhengzhou Engineering Research Center for High Performance Organic Functional Materials, Zhengzhou Institute of Technology, Zhengzhou 450044;
b Key Laboratory of Synthetic and Self-assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
c Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 320027

Received:2018-08-28 Revised:2018-10-25 Published:2018-11-12
Contact: 10.6023/cjoc201808034 E-mail:liws@mail.sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21474129, 21674125, 51761145043), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB20020000), the Science and Technology Open Cooperation Projects of Henan Province (Nos. 162106000018, 172106000067) and the Zhengzhou Institute of Technology.

1. Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution.PDF(1446KB)

Abstract

Fluorination on conjugated components is one of popular strategies to modify organic optoelectronic materials. Following the research of a benzodithiophene/benzothiadiazole ADA-type optoelectronic molecule, two benzothiadiazole (BT) units were fluorinated with different numbers and positions, and the change in basic properties and performances for field-effect transistors and organic solar cells was investigated. It was found that when the F-substitution number increases, the molecule enhances thermal stability, decreases solubility, lowers HOMO and LUMO energy levels, but almost does not alter light absorption range. Furthermore, investigations on organic field-effect transistors found the molecular hole mobility reduces with only one F-substituent at outer position of BT units, while increases up to 0.27 cm²·V^-1·s^-1 with two F substituents on BT units. However, when these materials are applied in organic solar cells, the fluorinated ones enhance open-circuit voltage, but deteriorate active layer morphology, finally leading to decrease in short-circuit current and device efficiency.

Key words: organic optoelectronic materials, fluorination effect, organic field-effect transistors, organic solar cells

Cite this article

Liang Long, Liu Li-Na, Chen Xue-Qiang, Xiang Xuan, Ling Jun, Lu Zheng-Quan, Li Jing-Jing, Li Wei-Shi. Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution[J]. Chin. J. Org. Chem., 2019, 39(1): 157-169.

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[1] (a) Brabec, C. J.; Gowrisanker, S.; Halls, J. J. M.; Laird, D.; Jia, S.; Williams, S. P. Adv. Mater. 2010, 22, 3839.
(b) Facchetti, A. Chem. Mater. 2011, 23, 733.
(c) Ilmi, R.; Haque, A.; Khan, M. S. Org. Electr. 2018, 58, 53.
(d) Guo, H.; Li, W.; Chang, C.; Guo, X.; Zhang, M. Chin. J. Chem. 2018, 36, 502.
(e) Liang, X.; Wang, Z.; Wang, L.; Hanif, M.; Hu, D.; Su, S.; Xie, Z.; Gao, Y.; Yang, B.; Ma, Y. Chin. J. Chem. 2017, 35, 1559.
[2] (a) Zhao, X.; Zhan, X. Chem. Soc. Rev. 2011, 40, 3728.
(b) Di, C.; Yu, G.; Liu, Y.; Zhu, D. J. Phys. Chem. B 2007, 111, 14083.
(c) Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296.
[3] (a) Reineke, S.; Lindner, F.; Schwartz, G.; Seidler, N.; Walzer, K.; Lüssem, B.; Leo, K. Nature 2009, 459, 234.
(b) Yang, X.; Zhou, G.; Wong, W. Y. Chem. Soc. Rev. 2015, 44, 8484.
(c) Jou, J. H.; Kumar, S.; Agrawal, A.; Li, T. H.; Sahoo, S. J. Mater. Chem. C 2015, 3, 2974.
[4] Chem, H.; Chen, Y.; Li, Z.; Yang, Q.; Xin, L. Chin. J. Org. Chem. 2012, 32, 46(in Chinese). (陈红海, 陈玉哲, 李仲谨, 杨清正, 辛利, 有机化学, 2012, 32, 46.)
[5] (a) Zhang, G.; Zhang, K.; Yin, Q.; Jiang, X. F.; Wang, Z.; Xin, J.; Ma, W.; Yan, H.; Huang, F.; Cao, Y. J. Am. Chem. Soc. 2017, 139, 2387.
(b) Li, M.; Gao, K.; Wan, X.; Zhang, Q.; Kan, B.; Xia, R.; Liu, F.; Yang, X.; Feng, H.; Ni, W.; Wang, Y.; Peng, J.; Zhang, H.; Liang, Z.; Yip, H.-L.; Peng, X.; Cao, Y.; Chen, Y. Nat. Photonics 2017, 11, 85.
(c) Zhao, J.; Li, Y.; Yang, G.; Jiang, K.; Lin, H.; Ade, H.; Ma, W.; Yan, H. Nat. Energy 2016, 1, 15027.
(d) Deng, D.; Zhang, Y. J.; Zhang, J. Q.; Wang, Z. Y.; Zhu, L. Y.; Fang, J.; Xia, B. Z.; Wang, Z.; Lu, K.; Ma, W.; Wei, Z. X. Nat. Commun. 2016, 7, 13740.
(e) Li, Y. F. Acc. Chem. Res. 2012, 45, 723.
(f) Yang, F.; Li, C.; Lai, W.; Zhang, A.; Huang, H.; Li, W. Mater. Chem. Front. 2017, 1, 1389.
(g) Liu, W.; Zhou, Z.; Vergote, T.; Xu, S.; Zhu, X. Mater. Chem. Front. 2017, 1, 2349.
[6] (a) Zhang, J.; Zhang, Y.; Fang, J.; Lu, K.; Wang, Z.; Ma, W.; Wei, Z. J. Am. Chem. Soc. 2015, 137, 8176.
(b) Li, G.; Chu, C. W.; Shrotriya, V.; Huang, J.; Yang, Y. Appl. Phys. Lett. 2006, 88, 253503.
(c) Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T. Q.; Dante, M.; Heeger, A. J. Science 2007, 317, 222.
(d) He, Z.; Zhong, C.; Huang, X.; Wong, W.-Y.; Wu, H.; Chen, L.; Su, S.; Cao, Y. Adv. Mater. 2011, 23, 4636.
[7] (a) Li, G.; Shrotriya, V.; Huang, J. S.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. Nat. Mater. 2005, 4, 864.
(b) Peet, J.; Kim, J. Y.; Coates, N. E.; Ma, W. L.; Moses, D.; Heeger, A. J.; Bazan, G. C. Nat. Mater. 2007, 6, 497.
(c) Zimmerman, J. D.; Xiao, X.; Renshaw, C. K.; Wang, S.; Diev, V. V.; Thompson, M. E.; Forrest, S. R. Nano Lett. 2012, 12, 4366.
(d) Wang, J. L.; Xiao, F.; Yan, J.; Wu, Z.; Liu, K. K.; Chang, Z. F.; Zhang, R. B.; Chen, H.; Wu, H. B.; Cao, Y. Adv. Funct. Mater. 2016, 26, 1803.
(e) Liu, X.; Ye, L.; Zhao, W.; Zhang, S.; Li, S.; Su, G. M.; Wang, C.; Ade, H.; Hou, J. Mater. Chem. Front. 2017, 1, 2057.
[8] (a) Neugebauer, H.; Brabec, C.; Hummelen, J. C.; Sariciftci, N. S. Sol. Energy Mater. Sol. Cells 2000, 61, 35.
(b) Lu, L.; Kelly, M. A.; You, W.; Yu, L. Nat. Photonics 2015, 9, 491.
(c) Min, J.; Luponosov, Y. N.; Gasparini, N.; Richter, M.; Bakirov, A. V.; Shcherbina, M. A.; Chvalun, S. N.; Grodd, L.; Grigorian, S.; Ameri, T.; Ponomarenko, S. A.; Brabec, C. J. Adv. Energy Mater. 2015, 5, 1500386.
[9] Meng, L.; Zhang, Y.; Wan, X.; Li, C.; Zhang, X.; Wang, Y.; Ke, X.; Xiao, Z.; Ding, L.; Xia, R.; Yip, H.-L.; Cao, Y.; Chen, Y. Science 2018, 361, 1094.
[10] (a) Lei, Y.; Deng, P.; Zhang, Q.; Xiong, Z.; Li, Q.; Mai, J.; Lu, X.; Zhu, X.; Ong, B. S. Adv. Funct. Mater. 2018, 28, 1706372.
(b) Kang, I.; Yun, H. J.; Chung, D. S.; Kwon, S. K.; Kim, Y. H. J. Am. Chem. Soc. 2013, 135, 14896.
[11] (a) Xiao, S.; Zhang, Q.; You, W. Adv. Mater. 2017, 29, 1601391.
(b) Zhang, Z.; Li, Y. Sci. China:Chem. 2015, 58, 192.
(c) Chen, H.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G. W.; Yang, Y.; Yu, L.; Wu, Y.; Li, G. Nat. Photonics 2009, 3, 649.
[12] (a) Tang, M. L.; Bao, Z. A. Chem. Mater. 2011, 23, 446.
(b) Oh, J.; Kranthiraja, K.; Lee, C.; Gunasekar, K.; Kim, S.; Ma, B.; Kim, B. J.; Jin, S.-H. Adv. Mater. 2016, 28, 10016.
(c) Stuart, A. C.; Tumbleston, J. R.; Zhou, H.; Li, W.; Liu, S.; Ade, H.; You, W. J. Am. Chem. Soc. 2013, 135, 1806.
[13] (a) Zhang, M.; Guo, X.; Zhang, S.; Hou, J. Adv. Mater. 2014, 26, 1118.
(b) Kawashima, K.; Fukuhara, T.; Suda, Y.; Suzuki, Y.; Koganezawa, T.; Yoshida, H.; Ohkita, H.; Osaka, I.; Takimiya, K. J. Am. Chem. Soc. 2016, 138, 10265.
[14] Reichenbacher, K.; Suss, H. I.; Hulliger, J. Chem. Soc. Rev. 2005, 34, 22.
[15] Lu, L.; Yu, L. Adv. Mater. 2014, 26, 4413.
[16] (a) Yoon, M.-H.; DiBenedetto, S. A.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 1348.
(b) Heidenhain, S. B.; Sakamoto, Y.; Suzuki, T.; Miura, A.; Fujikawa, H.; Mori, T.; Tokito, S.; Taga, Y. J. Am. Chem. Soc. 2000, 122, 10240.
[17] Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792.
[18] Son, H. J.; Wang, W.; Xu, T.; Liang, Y.; Wu, Y.; Li, G.; Yu, L. J. Am. Chem. Soc. 2011, 133, 1885.
[19] (a) Zhang, Y.; Chien, S.-C.; Chen, K.-S.; Yip, H.-L.; Sun, Y.; Davies, J. A.; Chen, F.-C.; Jen, A. K.-Y. Chem. Commun. 2011, 47, 11026.
(b) Schroeder, B. C.; Huang, Z.; Ashraf, R. S.; Smith, J.; D¢Angelo, P.; Watkins, S. E.; Anthopoulos, T. D.; Durrant, J. R.; McCulloch, I. Adv. Funct. Mater. 2012, 22, 1663.
[20] (a) Zhou, H.; Yang, L.; Stuart, A. C.; Price, S. C.; Liu, S.; You, W. Angew. Chem., Int. Ed. 2011, 50, 2995.
(b) Peng, Q.; Liu, X.; Su, D.; Fu, G.; Xu, J.; Dai, L. Adv. Mater. 2011, 23, 4554.
[21] Hu, J.; Wang, X.; Chen, F.; Xiao, B.; Tang, A.; Zhou, E. Polymers 2017, 9, 516.
[22] (a) Roncali, J. Acc. Chem. Res. 2009, 42, 1719.
(b) Li, Y.; Guo, Q.; Li, Z.; Pei, J.; Tian, W. Energy Environ. Sci. 2010, 3, 1427.
(c) Walker, B.; Kim, C.; Nguyen, T.-Q. Chem. Mater. 2011, 23, 470.
(d) Mishra, A.; Bauerle, P. Angew. Chem., Int. Ed. 2012, 51, 2020.
[23] Liang, L.; Wang, J.-T.; Xiang, X.; Ling, J.; Zhao, F.-G.; Li, W.-S. J. Mater. Chem. A 2014, 2, 15396.
[24] van der Poll, T. S.; Love, J. A.; Nguyen, T.-Q.; Bazan, G. C. Adv. Mater. 2012, 24, 3646.
[25] He, C.-Y.; Wu, C.-Z.; Zhu, Y.-L.; Zhang, X. Chem. Sci. 2014, 5, 1317.
[26] Mei, C.-Y.; Liang, L.; Zhao, F.-G.; Wang, J.-T.; Yu, L.-F.; Li, Y.-X.; Li, W.-S. Macromolecules 2013, 46, 7920.
[27] (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864.
(b) Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133.
(c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
(d) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
[28] (a) Hohenberg. P.; Kohn, W.; Phys. Rev. 1964, 136, B864(b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B:Condens. Matter Mater. Phys. 1988, 37, 785.
[29] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. J.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Gaussian, Inc., Wallingford CT, 2004.
[30] Wang, J.-L.; Chang, Z.-F.; Song, X.-X.; Liu, K.-K.; Jing, L.-M. J. Mater. Chem. 2015, 3, 9849.

苯并二噻吩/苯并噻二唑ADA型光电化合物:氟取代的影响

Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution

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