Synthesis and Photovoltaic Properties of Silole-Containing Conjugated Polymers

doi:10.6023/A15040282

Acta Chim. Sinica ›› 2015, Vol. 73 ›› Issue (10): 1055-1060.DOI: 10.6023/A15040282 Previous Articles Next Articles

Article

新型噻咯共轭聚合物的合成及其光伏性能

李昱达^a, 张恒^c, 王迅昶^a, 汪锋^a,b, 夏养君^c

a 武汉工程大学绿色化工过程教育部重点实验室武汉 430073;
b 华南理工大学发光材料与器件国家重点实验室广州 510640;
c 兰州交通大学光电技术与智能控制教育部重点实验室兰州 730070

投稿日期:2015-04-26 发布日期:2015-07-17
通讯作者: 夏养君 E-mail:psfwang@wit.edu.cn, yjxia73@126.com
基金资助:
项目受国家自然科学基金(No.51103111)、教育部新世纪优秀人才支持计划(No.NCET-12-0714)、发光材料与器件国家重点实验室开发基金(No.2014-skllmd-11)、教育部留学人员科研启动基金资助.

Synthesis and Photovoltaic Properties of Silole-Containing Conjugated Polymers

Li Yuda^a, Zhang Heng^c, Wang Xunchang^a, Wang Feng^a,b, Xia Yangjun^c

a Key Laboratory for Green Chemical Engineering and Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430073;
b State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640;
c Key Laboratory of Opto-Technology and Intelligent Control of Ministry of Education, Lanzhou Jiaotong University, Lanzhou 730070

Received:2015-04-26 Published:2015-07-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51103111), the Education Ministry of China (No. NCET-12-0714), the Open Fund of the State Key Laboratory of Luminescent Materials and Devices (No. 2014-skllmd-11) and the Scientific Research Foundation for the Returned Overseas Chinese Scholars.

1. Synthesis and Photovoltaic Properties of Silole-Containing Conjugated Polymers.PDF(595KB)

Abstract

Siloles are a group of five-membered silacyclics that possess a unique low-lying LUMO level associated with s*-p* conjugation. Siloles exhibit high electron acceptability, unusual aggregation-induced emission (AIE) and have been utilized as light-emitting layers in the fabrication of electroluminescence devices. The incorporation of 2,3,4,5-tetraarylsiloles into the main chain of polymers is of interest and importance in chemistry and functionalities. Some optoelectronic properties, impossible for silole small molecules, may be realized with silole-containing polymers. In this paper, four donor-acceptor (D-A) conjugated polymers with electron-withdrawing silole units and electron-donating fluorene or silafluorene units have been synthesized and characterized by NMR, TGA, GPC, and elemental analysis measurement. The photophysical properties show that all the polymers exhibit broad absorption range covering the whole UV-vis spectral region of the sunlight. The HOMO energy levels of four polymers are lower than -5.2 eV and the LUMO energy levels of them are higher than -3.6 eV, so these polymers are promising candidates for the effective applications of polymer solar cells (PSCs). Therefore, the photovoltaic properties of the polymer as donor was investigated by fabricating the bulk-heterojunction (BHJ) solar cells with a typical structure of ITO/PEDOT:PSS/polymer:PC₆₁BM/Al. As a preliminary result, the BHJ devices based on PF-HSTBT, PF-HOSTBT, PSiF-HSTBT, and PSiF-HOSTBT showed the power conversion efficiencies (PCEs) of 1.18%, 0.62%, 1.2%, and 0.83%, respectively. The short-circuit current density (J_sc) and PCE values of PSCs based on PF-HSTBT and PSiF-HSTBT are higher than those of PF-HOSTBT and PSiF-HOSTBT because of the reduced steric hindrance and improved structural planarity.

Key words: siloles, fluorene, silafluorene, donor, polymer solar cells

Cite this article

Li Yuda, Zhang Heng, Wang Xunchang, Wang Feng, Xia Yangjun. Synthesis and Photovoltaic Properties of Silole-Containing Conjugated Polymers[J]. Acta Chim. Sinica, 2015, 73(10): 1055-1060.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Duan, C.-H.; Zhang, K.; Zhong, C.-M.; Huang, F.; Cao, Y. Chem. Soc. Rev. 2013, 42, 9071.

[2] Liu, S.-Q.; Zhang, G.-C.; Lu, J.-M.; Jia, J.-C.; Li, W.; Huang, F.; Cao, Y. J. Mater. Chem. C 2015, 3, 4372.

[3] Jia, T.; Peng, Z.-S.; Li, Q.; Xie, Y.-P.; Hou, Q.; Hou, L.-T. Synth. Met. 2015, 199, 14.

[4] Jia, T.; Peng, Z.-S.; Li, Q.; Zhu, T.; Hou, Q.; Hou, L.-T. New J. Chem. 2015, 39, 994.

[5] Wang, J.-X.; Xiao, M.-J.; Chen, W.-C.; Qiu, M.; Du, Z.-K.; Zhu, W.-G.; Wen, S.-G.; Wang, N.; Yang, R.-Q. Macromolecules 2014, 47, 7823.

[6] Chen, Y.-H.; Yan, Y.; Du, Z.-K.; Bao, X.-C.; Liu, Q.; Roy, V. A.; Sun, M.-Q.; Yang, R.-Q.; Lee, C.-S. J. Mater. Chem. C 2014, 2, 3921.

[7] Guo, J.; Hang, L.-L.; Bao, X.-C.; Du, Z.-K.; Wang, T.; Yang, R.-Q. J. Phy. Chem. C 2014, 118, 9368.

[8] Liu, S.-J.; Zhang, K.; Lu, J.-M.; Zhang, K.; Yip, H. L.; Huang, F.; Cao, Y. J. Am. Chem. Soc. 2013, 135, 15326.

[9] Hu, Z.-C.; Zhang, K.; Huang, F.; Cao, Y. Chem. Commun. 2015, 51, 5572.
[10] Liu, Z.; Xu, F.; Yan, D.-D. Acta Chim. Sinica 2014, 72, 171. (刘震, 徐丰, 严大东, 化学学报, 2014, 72, 171.)
[11] Li, X.-W.; Zhao, B.; Cao, Z.-C.; Shen, P.; Tan, S.-T. Acta Chim. Sinica 2012, 70, 2433. (李新炜, 赵斌, 曹镇财, 沈平, 谭松庭, 化学学报, 2012, 70, 2433.)
[12] Wang, F.; Luo, J.; Yang, K.-X.; Chen, J.-W.; Huang, F.; Cao, Y. Macromolecules 2005, 38, 2253.
[13] Tao, Q.; Xia, Y.-X.; Xu, X.-F.; Hedström, S.; Bäcke, O.; James, D. I.; Persson P.; Olsson, E.; Inganäs, O.; Hou, L.-T.; Zhu, W.-G.; Wang, E.-G. Macromolecules 2015, 48, 1009.
[14] Tan, H.; Deng, X.-P.; Yu, J.-T.; Zhao, B.-F.; Wang, Y.-F.; Liu, Y.; Zhu, W.-G.; Wu, H.-B.; Cao, Y. Macromolecules 2013, 46, 113.
[15] Hou, Q.; Hong, W.-B.; Zhang, Y.; Liu, J.-G.; Chen, Y.-Q.; Shi, G. J. Mater. Sci.-Mater. El. 2013, 24, 536.
[16] Cheng, Y.-J.; Yang, S.-H.; Hsu, C.-S. Chem. Rev. 2009, 109, 5868.
[17] Wang, E.-G.; Wang, L.; Lan, L.-F.; Luo, C.; Zhuang, W.-L.; Peng, J.-B.; Cao, Y. Appl. Phys. Lett. 2008, 92, 033307.
[18] Yang, R.-Q.; Tian, R.-Y.; Hou, Q.; Yang, W.; Cao, Y. Macromolecules 2003, 36, 7453.
[19] Chan, K. L.; McKiernan, M. J.; Towns, C. R.; Holmes, A. B. J. Am. Chem. Soc. 2005, 127, 7662.
[20] Wang, F.; Wang, L.; Chen, J.-W.; Cao, Y. Macromol. Rapid Commun. 2007, 28, 2012.
[21] Wang, F; Luo, J.; Chen, J.-W.; Huang, F.; Cao, Y. Polymer 2005, 46, 8422.
[22] Sirringhaus, H. Adv. Mater. 2005, 17, 2411.
[23] Usta, H.; Lu, G.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2006, 128, 9034.
[24] Liu, Q.; Bao, X.-C.; Wen, S.-Q.; Du, Z.-K.; Han, L.-Q.; Zhu, D.-Q.; Chen, Y.-H.; Sun, M.-L.; Yang, R.-Q. Polym. Chem. 2014, 5, 2076.
[25] Chen, Y.-H.; Du, Z.-K.; Chen, W.-C.; Wen, S.-Q.; Sun, L.; Liu, Q.; Sun, M.-L.; Yang, R.-Q. New J. Chem. 2014, 38, 1559.
[26] Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T.-Q.; Dante, M.; Heeger, A. J. Science 2007, 317, 222.
[27] Yamaguchi, S.; Endo, T.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Tamao, K. Chem.-Eur. J. 2000, 6, 1683.
[28] Agrawal, A. K.; Jenekhe, S. A. Chem. Mater. 1996, 8, 579.
[29] Ranger, M.; Rondeau, D.; Leclerc, M. Macromolecules 1997, 30, 7686.
[30] Chan, K. L.; McKiernan, M. J.; Towns, C. R.; Holmes, A. B. J. Am. Chem. Soc. 2005, 127, 7662.

新型噻咯共轭聚合物的合成及其光伏性能

Synthesis and Photovoltaic Properties of Silole-Containing Conjugated Polymers

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fengjie Ge, Kaizhi Zhang, Qingpeng Cao, Hui Xu, Tao Zhou, Wenhao Zhang, Xinxin Ban, Xiaobo Zhang, Na Li, Peng Zhu. Design, Synthesis and Electroluminescence Performance of Flexible Fluorenyl Block Delayed Fluorescence Dimers [J]. Acta Chimica Sinica, 2023, 81(9): 1157-1166.
[2]	Dongxu Li, Xiang Xu, Jiage Song, Songting Liang, Yuang Fu, Xinhui Lu, Yingping Zou. Rotaxane Structure Optimizes the Photovoltaic Performance of Polymer Solar Cells^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1500-1507.
[3]	Yuyu Liu, Jiefeng Chen, Zhen Shao, Ying Wei, Haifeng Ling, Linghai Xie. Ambipolar Organic Field Effect Transistor Memory Based on H-Type Fluorene-Based Small Molecule [J]. Acta Chimica Sinica, 2023, 81(11): 1508-1514.
[4]	Mingrui Pu, Feng He. Chlorine-Mediated Organic Photovoltaic Materials^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1541-1550.
[5]	Yuguang Sui, Jinrong Zhou, Pan Liao, Wenjie Liang, Hai Xu. A Gaint Donor-Acceptor Molecular Switch Compound: Synthesis and Properties [J]. Acta Chimica Sinica, 2022, 80(8): 1061-1065.
[6]	Bin Liu, Pangkuan Chen. Synthesis and Properties of Novel Circularly Polarized Luminescence Materials Based on Binaphthol Skeleton [J]. Acta Chimica Sinica, 2022, 80(7): 929-935.
[7]	Wenyuan Lin, Qingzhe Zhu, Yunlong Ma, Peng Wang, Shuo Wan, Qingdong Zheng. Rationally Tuning Blend Miscibility of Polymer Donor and Nonfullerene Acceptor for Constructing Efficient Organic Solar Cells^※ [J]. Acta Chimica Sinica, 2022, 80(6): 724-733.
[8]	Hongtao Cao, Pengfei Hou, Qing Cao, Yanang Li, Shasha Wang, Linghai Xie. Exciplex Emission and Property Investigation Based on Cyano-substituted 9-Phenylfluorene Derivative [J]. Acta Chimica Sinica, 2022, 80(11): 1476-1484.
[9]	Xinming Hu, Chunxiao Zhong, Xiaoyan Li, Xiong Jia, Ying Wei, Linghai Xie. Synthesis and Application of Cyclopentadithiophene Derivatives [J]. Acta Chimica Sinica, 2021, 79(8): 953-966.
[10]	Yang Bai, Ling-Wei Xue, Hai-Qiao Wang, Zhi-Guo Zhang. Research Advances on Benzotriazole-based Organic Photovoltaic Materials [J]. Acta Chimica Sinica, 2021, 79(7): 820-852.
[11]	Junhui Miao, Zicheng Ding, Jun Liu, Lixiang Wang. Research Progress in Organic Solar Cells Based on Small Molecule Donors and Polymer Acceptors [J]. Acta Chimica Sinica, 2021, 79(5): 545-556.
[12]	Min Lv, Ruimin Zhou, Kun Lu, Zhixiang Wei. Research Progress of Small Molecule Donors with High Crystallinity in All Small Molecule Organic Solar Cells [J]. Acta Chimica Sinica, 2021, 79(3): 284-302.
[13]	Hu Yuhui, Wu Wenlin, Yu Liyang, Luo Kaijun, Xu Xiaopeng, Li Ying, Peng Qiang. Synthesis and Photovoltaic Properties of Perylene Diimide Based Small Molecular Acceptors with a Diketopyrrolopyrrole Core [J]. Acta Chimica Sinica, 2020, 78(11): 1246-1254.
[14]	Ren Bao-Yi, Yi Jian-Cheng, Zhong Dao-Kun, Zhao Yu-Zhi, Guo Run-Da, Sheng Yong-Gang, Sun Ya-Guang, Xie Ling-Hai, Huang Wei. Conjugated Regulation of Phosphorescent Iridium (III) Complex Constructed from Spiro Ligand and Its Electroluminescent Performances [J]. Acta Chimica Sinica, 2020, 78(1): 56-62.
[15]	Bo Yifan, Liu Yuyu, Chang Yongzheng, Li Yinxiang, Zhang Xiaofei, Song Chunyuan, Xu Weifeng, Cao Hongtao, Huang Wei. Theoretical and Experimental Studies on Raman Spectroscopy of Cyclic Fluorene-Based Strained Semiconductors [J]. Acta Chim. Sinica, 2019, 77(5): 442-446.