Chinese Journal of Organic Chemistry >
Synthesis and Electroluminescent Properties of Red-Emitting Iridium Complexes Based on Benzofuran-Isoquinoline
Received date: 2021-12-28
Revised date: 2022-01-27
Online published: 2022-02-18
Supported by
Natural Science Foundation of China(U2001222); Natural Science Foundation of China(21975055); Natural Science Foundation of China(21975053)
Three red iridium complexes were designed and synthesized by employing 6-isopropyl-1-(5-methylbenzofuran-7- yl)isoquinoline, 6-cyclopentyl-1-(5-methylbenzofuran-7-yl)isoquinoline and 6-isobutyl-1-(5-methylbenzofuran-7-yl)isoquinoline as main ligands, respectively, and 3,7-diethyl-4,6-nonedione as the auxiliary ligand. Their photophysical, thermal and electrochemical properties were investigated. These complexes have higher photoluminescence quantum yields and shorter phosphorescent lifetime. Three organic electroluminescent devices with same structure were fabrication using the iridium complexes as emitters. They all exhibited red electroluminescent emission with peak values at 637, 635 and 636 nm, respectively and showed low turn-on voltages below 2.8 V. And the highest external quantum efficiency of three devices was 14.1%, 13.4% and 13.3%, the highest current efficiency was 7.0, 7.4 and 7.0 cd/A, and the highest power efficiency was 7.9, 8.3, and 7.8 lm/W, respectively. These data indicate that the three iridium complexes can be used as efficient red phosphorescent materials.
Fei Nie , Guanbo Huang , Lei Dai , Shaofu Chen , Shaomin Ji , Jiaxiong Chen , Yanping Huo . Synthesis and Electroluminescent Properties of Red-Emitting Iridium Complexes Based on Benzofuran-Isoquinoline[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1423 -1430 . DOI: 10.6023/cjoc202112039
| [1] | Qiu, Z. P.; Tan, J. H.; Cai, N.; Wang, K.; Ji, S. M.; Huo, Y. P. Chin. J. Org. Chem. 2019, 39, 679. (in Chinese) |
| [1] | (邱志鹏, 谭继华, 蔡宁, 王凯, 籍少敏, 霍延平, 有机化学, 2019, 39, 679.) |
| [2] | Kang, S.; Jung, H.; Lee, H.; Park, S.; Kim, J.; Park, J. J. Mater. Chem. C 2019, 7, 14709. |
| [3] | Li, G.; Zheng, J.; Klimes, K.; Zhu, Z. Q.; Wu, J.; Zhu, H.; Li, J. ACS Appl. Mater. Interfaces 2019, 11, 40320. |
| [4] | Liang, Z.-P.; Tang, R.; Qiu, Y.-C.; Wang, Y.; Lu, H.; Wu, Z.-G. Acta Chim. Sinica 2021, 79, 1401. (in Chinese) |
| [4] | (梁志鹏, 唐瑞, 邱雨晨, 王阳, 陆洪彬, 吴正光, 化学学报, 2021, 79, 1401.) |
| [5] | Mao, X.; Xie, F.; Wang, X.; Wang, Q.; Qiu, Z.; Elsegood, M. R. J.; Bai, J.; Feng, X.; Redshaw, C.; Huo, Y.; Hu, J. Y.; Chen, Q. Chin. J. Chem. 2021, 39, 2154. |
| [6] | Sun, N.; Jiang, C.; Li, Q.; Tan, D.; Bi, S.; Song, J. J. Mater. Sci.: Mater. Electron. 2020, 31, 20688. |
| [7] | Tian, Q. S.; Yuan, S.; Shen, W. S.; Zhang, Y. L.; Wang, X. Q.; Kong, F. C.; Liao, L. S. Adv. Opt. Mater. 2020, 8, 2000556. |
| [8] | Vadagaonkar, K. S.; Yang, C.-J.; Zeng, W.-H.; Chen, J.-H.; Patil, B. N.; Chetti, P.; Chen, L.-Y.; Chaskar, A. C. Dyes Pigm. 2019, 160, 301. |
| [9] | Wei, Q.; Fei, N.; Islam, A.; Lei, T.; Hong, L.; Peng, R.; Fan, X.; Chen, L.; Gao, P.; Ge, Z. Adv. Opt. Mater. 2018, 6, 1800512. |
| [10] | Yang, X.; Jiao, B.; Dang, J. S.; Sun, Y.; Wu, Y.; Zhou, G.; Wong, W. Y. ACS Appl. Mater. Interfaces. 2018, 10, 10227. |
| [11] | Zhao, J.-H.; Hu, Y.-X.; Lu, H.-Y.; Lü, Y.-L.; Li, X. Org. Electron. 2017, 41, 56. |
| [12] | Tan, J. H.; Huo, Y. P.; Cai, N.; Ji, S. M.; Li, Z. Z.; Zhang, L. Chin. J. Org. Chem. 2017, 37, 2457. (in Chinese) |
| [12] | (谭继华, 霍延平, 蔡宁, 籍少敏, 李宗植, 张力, 有机化学, 2017, 37, 2457.) |
| [13] | Lepeltier, M.; Dumur, F.; Wantz, G.; Vila, N.; Mbomekallé, I.; Bertin, D.; Gigmes, D.; Mayer, C. R. J. Lumin. 2013, 143, 145. |
| [14] | Liang, B.; Jiang, C.; Chen, Z.; Zhang, X.; Shi, H.; Cao, Y. J. Mater. Chem. 2006, 16, 1281. |
| [15] | Ouyang, X.; Chen, D.; Zeng, S.; Zhang, X.; Su, S.; Ge, Z. J. Mater. Chem. 2012, 22, 23005. |
| [16] | Thamilarasan, V.; Jayamani, A.; Manisankar, P.; Kim, Y.-I.; Sengottuvelan, N. Inorg. Chim. Acta 2013, 408, 240. |
| [17] | Ulbricht, C.; Beyer, B.; Friebe, C.; Winter, A.; Schubert, U. S. Adv. Mater. 2009, 21, 4418. |
| [18] | Yang, X.; Guo, H.; Liu, B.; Zhao, J.; Zhou, G.; Wu, Z.; Wong, W. Y. Adv. Sci. 2018, 5, 1701067. |
| [19] | Yang, X.; Zhou, G.; Wong, W. Y. Chem. Soc. Rev. 2015, 44, 8484. |
| [20] | Laskar, I. R.; Hsu, S.-F.; Chen, T.-M. Polyhedron 2005, 24, 189. |
| [21] | Tobita, S.; Yoshihara, T. Curr. Opin. Chem. Biol. 2016, 33, 39. |
| [22] | Sun, Y.; Yang, X.; Feng, Z.; Liu, B.; Zhong, D.; Zhang, J.; Zhou, G.; Wu, Z. ACS Appl. Mater. Interfaces 2019, 11, 26152. |
| [23] | Wang, D. Q. M.S. Thesis, Yunnan Normal University, Yunnan, 2019. (in Chinese) |
| [23] | (王登强, 硕士论文,云南师范大学,云南, 2019.) |
| [24] | Zhuang, J.; Li, W.; Su, W.; Liu, Y.; Shen, Q.; Liao, L.; Zhou, M. Org. Electron. 2013, 14, 2596. |
| [25] | Wang, X. M.S. Thesis, Dalian University of Technology, Dalian, 2011. (in Chinese) |
| [25] | (王馨, 硕士论文,大连理工大学,大连, 2011.) |
| [26] | Su, Y. J.; Huang, H. L.; Li, C. L.; Chien, C. H.; Tao, Y. T.; Chou, P. T.; Datta, S.; Liu, R. S. Adv. Mater. 2003, 15, 884. |
| [27] | Lips, S.; Frontana-Uribe, B. A.; Dorr, M.; Schollmeyer, D.; Franke, R.; Waldvogel, S. R. Chem.-Eur. J. 2018, 24, 6057. |
/
| 〈 |
|
〉 |
