Novel Small Four-armed Molecules with Triphenylamine-bridged Structure for Organic Solar Cells Featuring High Open-circuit Voltage

doi:10.1007/s40242-019-9179-1

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (6): 1032-1039.doi: 10.1007/s40242-019-9179-1

Novel Small Four-armed Molecules with Triphenylamine-bridged Structure for Organic Solar Cells Featuring High Open-circuit Voltage

HE Xiaodong¹, ZHU Jianling², YIN Lunxiang¹, XIE Bao¹, LI Kechang², LI Yanqin¹

1. School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China;
2. College of Chemistry, Jilin University, Changchun 130012, P. R. China

收稿日期:2019-06-26 修回日期:2019-08-13 出版日期:2019-12-01 发布日期:2019-11-29
通讯作者: LI Yanqin E-mail:liyanqin@dlut.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21102013) and the Fundamental Funds for the Central Universities, China(No.DUT16ZD205).

Novel Small Four-armed Molecules with Triphenylamine-bridged Structure for Organic Solar Cells Featuring High Open-circuit Voltage

HE Xiaodong¹, ZHU Jianling², YIN Lunxiang¹, XIE Bao¹, LI Kechang², LI Yanqin¹

1. School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China;
2. College of Chemistry, Jilin University, Changchun 130012, P. R. China

Received:2019-06-26 Revised:2019-08-13 Online:2019-12-01 Published:2019-11-29
Contact: LI Yanqin E-mail:liyanqin@dlut.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21102013) and the Fundamental Funds for the Central Universities, China(No.DUT16ZD205).

摘要/Abstract

摘要： In view of few attention on star-shaped molecules containing triphenylamine(TPA) unit as π-linker, a series of small four-armed molecules, consisting of octyloxy-substituted 2,1,3-benzothiadiazole(DOBT) or 4-octyl-2-thienyl functionalized DOBT as the core, TPA as π-bridge and 4-methylphenyl or 4-methoxyphenyl groups as terminal units, was designed and synthesized. The effects of π-bridges and substitute groups on molecular photoelectric performance and photovoltaic performance were fully explored. With the help of the additional thiophene-linkers incorporation, 3-octylthienyl substituted molecule with end-capping 4-methylphenyl(T-BTTPAM) and 3-octylthienyl substituted molecule with end-capping 4-methoxyphenyl(T-BTTPAOM) showed stronger and broader absorption, as well as higher charge mobilities compared to the molecules without thiophene-linkers(BTTPAM and BTTPAOM). Additionally, changing substitute groups from methyl to methoxy helped BTTPAOM and T-BTTPAOM achieve better absorption properties than BTTPAM and T-BTTPAM, respectively. When paired with PC₆₁BM as the electron acceptor to fabricate solution-processed photovoltaic devices, the four materials gave high open-circuit voltage(V_oc) values over 0.90 V. These results demonstrate that our materials are promising candidates as donor materials for organic solar cells(OSCs), and further device optimization is in progress in our laboratory.

关键词: Triphenylamine, Four-armed structure, High open-circuit voltage, Organic solar cell, Small-molecule donor

Abstract: In view of few attention on star-shaped molecules containing triphenylamine(TPA) unit as π-linker, a series of small four-armed molecules, consisting of octyloxy-substituted 2,1,3-benzothiadiazole(DOBT) or 4-octyl-2-thienyl functionalized DOBT as the core, TPA as π-bridge and 4-methylphenyl or 4-methoxyphenyl groups as terminal units, was designed and synthesized. The effects of π-bridges and substitute groups on molecular photoelectric performance and photovoltaic performance were fully explored. With the help of the additional thiophene-linkers incorporation, 3-octylthienyl substituted molecule with end-capping 4-methylphenyl(T-BTTPAM) and 3-octylthienyl substituted molecule with end-capping 4-methoxyphenyl(T-BTTPAOM) showed stronger and broader absorption, as well as higher charge mobilities compared to the molecules without thiophene-linkers(BTTPAM and BTTPAOM). Additionally, changing substitute groups from methyl to methoxy helped BTTPAOM and T-BTTPAOM achieve better absorption properties than BTTPAM and T-BTTPAM, respectively. When paired with PC₆₁BM as the electron acceptor to fabricate solution-processed photovoltaic devices, the four materials gave high open-circuit voltage(V_oc) values over 0.90 V. These results demonstrate that our materials are promising candidates as donor materials for organic solar cells(OSCs), and further device optimization is in progress in our laboratory.

Key words: Triphenylamine, Four-armed structure, High open-circuit voltage, Organic solar cell, Small-molecule donor

HE Xiaodong, ZHU Jianling, YIN Lunxiang, XIE Bao, LI Kechang, LI Yanqin. Novel Small Four-armed Molecules with Triphenylamine-bridged Structure for Organic Solar Cells Featuring High Open-circuit Voltage[J]. 高等学校化学研究, 2019, 35(6): 1032-1039.

参考文献

[1] Yadagiri B., Narayanaswamy K., Revoju S., Eliasson B., Sharma G. D., Singh S. P., J. Mater. Chem. C, 2019, 7, 709
[2] Lin Y. C., Lu Y. J., Tsao C. S., Saeki A., Li J. X., Chen C. H., Wang H. C., Chen H. C., Meng D., Wu K. H., Yang Y., Wei K. H., J. Mater. Chem. A, 2019, 7, 3027
[3] Xu X., Yu T., Bi Z., Ma W., Li Y., Peng Q., Adv. Mater., 2018, 30, 1703973
[4] Zhou L., Guan S., Li L., Zhao L., Chem. Res. Chinese Universities, 2015, 31(5), 801
[5] Meng L., Wan X., Li C., Zhang X., Wang Y., Xiao Z., Ding L., Xia R., Yip H. L., Chao Y., Chen Y., Science, 2018, 361, 1094
[6] Revoju S., Biswas S., Eliasson B., Sharma G. D., Phys. Chem. Chem. Phys., 2018, 20, 6390
[7] He X., Yin L., Li Y., New J. Chem., 2019, 43, 6577
[8] Geng Y., Tang A., Tajima K., Zeng Q., Zhou E., J. Mater. Chem. A., 2019, 7, 64
[9] Bin H., Yao J., Yang Y., Angunawela I., Sun C., Gao L., Ye L., Qiu B., Xue L., Zhu C., Yang C., Zhang Z. G., Ade H., Li Y., Adv. Mater., 2018, 30, 1706361
[10] Tu Q., Yin Z., Ma Y., Chen S. C., Zheng Q., Dyes Pigm., 2018, 149, 747
[11] Kim S. W., Lee Y. J., Lee Y. W., Koh C. W., Lee Y., Kim M. J., Liao K., Cho J. H., Kim B. J., Woo H. Y., ACS Appl. Mater. Interfaces., 2018, 10, 39952
[12] Wan J., Xu X., Zhang G., Li Y., Feng K., Peng Q., Energy Environ. Sci., 2017, 10, 1739
[13] Song J., Xue X., Fan B., Huo L., Sun Y., Mater. Chem. Front., 2018, 2, 1626
[14] Deng J., Chen J., Tao Q., Yan D., Fu Y., Tan H., Tetrahedron, 2018, 74, 3989
[15] Malytskyi V., Simon J. J., Patrone L., Raimundo J. M., RSC Adv., 2015, 5, 354
[16] Zhang Q., Xiao B., Du M., Li G., Tang A., Zhou E., J. Mater. Chem. C, 2018, 6, 10902
[17] Wang H., Yue Q., Nakagawa T., Zieleniewska A., Okada H., Ogumi K., Ueno H., Guldi D. M., Zhu X., Matsuo Y., J. Mater. Chem. A, 2019, 7, 4072
[18] Yang D., Yang Q., Yang L., Luo Q., Huang Y., Lu Z., Zhao S., Chem. Commun., 2013, 49, 10465
[19] Vybornyi O., Jiang Y., Baert F., Demeter D., Roncali J., Blanchard P., Cabanetos C., Dyes Pigm., 2015, 115, 17
[20] Liu X., Xie Y., Zhao H., Cai X., Wu H., Su S. J., Cao Y., New J. Chem., 2015, 39, 8771
[21] Wang Q., Duan L., Tao Q., Peng W., Chen J., Tan H., Yang R., Zhu W., ACS Appl. Mater. Interfaces, 2016, 8, 30320
[22] Yuan C., Liu W., Shi M., Li S., Wang Y., Chen H., Li C. Z., Chen H., Dyes Pigm., 2017, 143, 217
[23] Jia T., Peng Z., Li Q., Zhu T., Hou Q., Hou L., New J. Chem., 2015, 39, 994
[24] Wang J., Liu K., Ma L., Zhan X., Chem. Rev., 2016, 116, 14675
[25] Zhen H., Peng Z., Hou L., Jia T., Li Q., Hou Q., Dyes Pigm., 2015, 113, 451
[26] Zhi Y., Zhao B., Cao R., Xu Y., Wang J., Dang D., Gao C., Meng L., Dyes Pigm., 2018, 153, 291
[27] Wang L., Yin L., Wang L., Xie B., Ji C., Li Y., Dyes Pigm., 2017, 140, 203
[28] Blom P. W. M., Jong M. J. M., Munster G. M., Phys. Rev. B, 1997, 55, 656
[29] Li Z., Dong Q., Li Y., Xu B., Deng M., Pei J., Zhang J., Chen F., Wen S., Gao Y., Tian W., J. Mater. Chem., 2011, 21, 2159
[30] Ji C., Yin L., Wang L., Jia T., Meng S., Sun Y., Li Y., J. Mater. Chem. C, 2014, 2, 4019
[31] Zeng S., Yin L., Ji C., Jiang X., Li K., Li Y., Wang Y., Chem. Commun., 2012, 48, 10627
[32] Wang L., Yin L., Ji C., Li Y., Dyes Pigm., 2015, 118, 37
[33] Lin Y., Li Y., Zhan X., Adv. Energy Mater., 2013, 3, 724
[34] Shi H., Fu W., Shi M., Ling J., Chen H., J. Mater. Chem. A, 2015, 3, 1902
[35] Fan Q., Xu Z., Guo X., Meng X., Li W., Su W., Ou X., Ma W., Zhang M., Li Y., Nano Energy, 2017, 40, 20
[36] Fan Q., Liu Y., Xiao M., Su W., Gao H., Chen J., Tan H., Wang Y., Yang R., Zhu W., J. Mater. Chem. C, 2015, 3, 6240
[37] He X., Yin L., Li Y., J. Mater. Chem. C, 2019, 7, 2487
[38] Bai H., Wang Y., Cheng P., Li Y., Zhu D., Zhan X., ACS Appl. Mater. Interfaces, 2014, 6, 8426

Novel Small Four-armed Molecules with Triphenylamine-bridged Structure for Organic Solar Cells Featuring High Open-circuit Voltage

Novel Small Four-armed Molecules with Triphenylamine-bridged Structure for Organic Solar Cells Featuring High Open-circuit Voltage

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 4

编辑推荐

Metrics

本文评价

[1]	WANG Yuheng, CHANG Yilin, ZHANG Jianqi, LU Guanghao, WEI Zhixiang. Semitransparent Flexible Organic Solar Cells[J]. 高等学校化学研究, 2020, 36(3): 343-350.
[2]	ZOU Liyun, GUAN Shuang, LI Leijiao, ZHAO Li. Dipyrrin-based Complexes for Solution-processed Organic Solar Cells[J]. 高等学校化学研究, 2015, 31(5): 801-808.
[3]	QIAO Wen-qiang. Design, Synthesis and Electrochromic Properties of Anthraquinone Imide-based Donor-acceptor Type of Near Infrared Chromophores[J]. 高等学校化学研究, 2012, 28(2): 239-241 .
[4]	Lü Hai-jun, LI Xiang-gao, WANG Shi-rong, GAO Wen-zheng, WANG Sha-sha. Synthesis and Properties of Novel Luminescent Compounds Containing Triphenylamine and Bipyridine Units[J]. 高等学校化学研究, 2012, 28(2): 313-318 .