Unsymmetric Phosphorescent Ir(III) Complexes with Ambipolar Features and Investigation for Both Aggregation-Induced Phosphorescent Emission and Electroluminescent Properties

doi:10.6023/cjoc202403052

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非对称双极性Ir(III)配合物磷光分子及其聚集诱导磷光和电致发光性能研究

陈姿仪^a, 刘思琪^a, 冯钊^a, 钟道昆^a, 杨晓龙^a, 孙源慧^a, 徐先彬^b, 冯震^b, 岳岭^a,*, 周桂江^a,*

^a西安交通大学化学学院陕西西安 710049;
^b陕西莱特光电材料有限公司陕西西安 710065

收稿日期:2024-03-30 修回日期:2024-05-22
基金资助:
国家自然科学基金(No. 52161145411, 21875179, 22175137, 21602170 及51803163)资助.

Unsymmetric Phosphorescent Ir(III) Complexes with Ambipolar Features and Investigation for Both Aggregation-Induced Phosphorescent Emission and Electroluminescent Properties

Ziyi Chen^a, Siqi Liu^a, Zhao Feng^a, Daokun Zhong^a, Xiaolong Yang^a, Yuanhui Sun^a, Xianbin Xu^a, Zhen Feng^a, Ling Yue^a,*, Guijiang Zhou^a,*

^aSchool of Chemistry, Xi'an Jiaotong University, Xi'an, 710049;
^bShaanxi Lighte Optoelectronics Material Co., Ltd. Xi'an, 710056

Received:2024-03-30 Revised:2024-05-22
Contact: * E-mail: heartstar@xjtu.edu.cn; zhougj@xjtu.edu.cn
Supported by:
the National Natural Science Foundation of China (No. 52161145411, 21875179, 22175137, 21602170 and 51803163).

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Abstract

Two unsymmetric Ir(III) phosphorescent complexes have been prepared with functionalized both 2-phenylpyridine(ppy)- and 2-vinylpyridine(vpy)-type ligands to investigate their optoelectronic properties. Photophysical results show that there are two kinds of radiative excited states contributing their phosphorescent emission. In addition, the unsymmetric Ir(III) phosphorescent complexes can exhibit aggregation-induced/enhanced phosphorescent emission behavior. Electrochemical results indicate that introducing functional group can confer ambipolar features to the unsymmetric Ir(III) phosphorescent complexes. In addition, they can show decent electroluminescent ability with turn-on voltage (V_turn-on) less than 3.0 V, maximum luminescence (L_max) of 11380 cd•m^-2, maximum external quantum efficiency (η_ext) of 5.3%, maximum current efficiency (η_L) of 12.9 cd•A^-1 and maximum power efficiency (η_P) of 13.6 lm•W^-1. All these results can provide valuable information for design and synthesis of new electroluminescent materials with aggregation-induced phosphorescent emission ability.

Key words: unsymmetric structure, Ir(III) phosphorescent complexes, aggregation-induced phosphorescent emission, ambipolar features, Electroluminescence

Cite this article

Ziyi Chen, Siqi Liu, Zhao Feng, Daokun Zhong, Xiaolong Yang, Yuanhui Sun, Xianbin Xu, Zhen Feng, Ling Yue, Guijiang Zhou. Unsymmetric Phosphorescent Ir(III) Complexes with Ambipolar Features and Investigation for Both Aggregation-Induced Phosphorescent Emission and Electroluminescent Properties[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202403052.

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[1] Duo Y.; Luo G.; Zhang W.; Wang R.; Xiao G. G.; Li Z.; Li X.; Chen M.; Yoon J.; Tang B. Z.Chem. Soc. Rev. 2023, 52 (3), 1024-1067.
[2] Hong Y.; Lam J. W.Y.; Tang, B. Z.Chem. Soc. Rev. 2011, 40 (11), 5361-5388.
[3] Mei J.; Leung N. L.C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z.Chem. Rev. 2015, 115 (21), 11718-11940.
[4] Wan Z.; Li Y.; Zhou Y.; Peng D.; Zhang X.; Zhuang J.; Lei B.; Liu Y.; Hu C.Adv. Funct. Mater. 2023, 33 (11), 2207296.
[5] Luo J.; Xie Z.; Lam J. W.Y.; Cheng, L.; Tang, B. Z.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D. Chem. Commun. 2001, (18), 1740-1741.
[6] Zhang Y.; Nie F.; Zhou L.; Wang X.; Liu Y.; Huo Y.; Chen W.; Zhao, Z. Chin. J. Org. Chem.2023, 43(11), 3876-3887.
[7] Zhao Y.; Chen P.; Han L.; Wang, E. Chin. J. Org. Chem.2023, 43 (7), 2454-2461.
[8] Ma D.; Zhang C.; Liu R.; Qiu Y.; Duan L.Chemistry - A European Journal 2018, 24 (21), 5574-5583.
[9] She P. F.; Zheng Z.; Qin Y. Y.; Li F. Y.; Zheng X. K.; Zhang D. D.; Xie Z. Y.; Duan L.; Wong W. Y.Adv. Opt. Mater. 2023, 2302132.
[10] Cho W.; Sarada G.; Lee H.; Song M.; Gal Y.-S.; Lee Y.; Jin S.-H.Dyes Pigm. 2017, 136, 390-397.
[11] Xie J.-X.; Lee C.-C.; Huang L.-M.; Lin H.-T.; Luo D.; Hsieh C.-H.; Liu S.-W.; Chen C.-H.ACS Appl. Mater. Interfaces 2023, 15 (37), 44022-44032.
[12] Yang L.; Zhang Y.; Zhang X.; Li N.; Quan Y.; Cheng Y.Chem. Commun. 2018, 54 (69), 9663-9666.
[13] Zhan Y.; Yang Z.; Tan J.; Qiu Z.; Mao Y.; He J.; Yang Q.; Ji S.; Cai N.; Huo Y.Dyes Pigm. 2020, 173, 107898.
[14] Wang Y.; Liu J.; Niu Y.; He L.; Wang Y.; Ma Y.; Yao Y.; Ye J.Adv. Opt. Mater. 2023, 11 (15), 2202940.
[15] Zhao J.; Feng Z.; Zhong D.; Yang X.; Wu Y.; Zhou G.; Wu Z.Chem. Mater. 2018, 30 (3), 929-946.
[16] Yao C.; Li B.; Jin Y.; Li H.; Yang X.; Sun Y.; Zhou G.; Jiao B.J. Mater. Chem. C 2021, 9 (36), 12330-12341.
[17] Lamansky S.; Djurovich P.; Murphy D.; Abdel-Razzaq, F.; Kwong, R.; Tsyba, I.; Bortz, M.; Mui, B.; Bau, R.; Thompson, M. E.Inorg. Chem. 2001, 40 (7), 1704-1711.
[18] Sprouse S.; King K. A.; Spellane P. J.; Watts R. J.J. Am. Chem. Soc. 2002, 106 (22), 6647-6653.
[19] Lamansky S.; Djurovich P.; Murphy D.; Abdel-Razzaq, F.; Lee, H.-E.; Adachi, C.; Burrows, P. E.; Forrest, S. R.; Thompson, M. E.J. Am. Chem. Soc. 2001, 123 (18), 4304-4312.
[20] Dong Q.; He B.; Qiao W.; Zhu W.; Duan P.; Wang Y.Chem. Commun. 2024, 60 (25), 3421-3424.
[21] Zhou G.; Ho C. L.; Wong W. Y.; Wang Q.; Ma D.; Wang L.; Lin Z.; Marder T. B.; Beeby A.Adv. Funct. Mater. 2008, 18 (3), 499-511.
[22] Liu S.; Feng Z.; Wang H.; Hang H.; Zhong D.; Yang X.; Sun Y.; Su B.; Xu X.; Feng Z.; Zhou G.; Jiao B.J. Mater. Chem. C 2023, 11 (40), 13824-13837.
[23] Xu X. B.; Yang X. L.; Dang J. S.; Zhou G. J.; Wu Y.; Li H.; Wong W. Y.Chem. Commun. 2014, 50 (19), 2473-2476.
[24] Wong W. Y.; Zhou G. J.; Yu X. M.; Kwok H. S.; Tang B. Z.Adv. Funct. Mater. 2006, 16 (6), 838-846.
[25] Yang X.; Xu X.; Zhao J.; Dang J.-s.; Huang, Z.; Yan, X.; Zhou, G.; Wang, D.Inorg. Chem. 2014, 53 (24), 12986-13000.

非对称双极性Ir(III)配合物磷光分子及其聚集诱导磷光和电致发光性能研究

Unsymmetric Phosphorescent Ir(III) Complexes with Ambipolar Features and Investigation for Both Aggregation-Induced Phosphorescent Emission and Electroluminescent Properties

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