Chinese Journal of Organic Chemistry >
Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones
Received date: 2023-03-15
Revised date: 2023-05-30
Online published: 2023-07-13
Supported by
National Natural Science Foundation of China(U2001222); National Natural Science Foundation of China(U22A20399); National Natural Science Foundation of China(52003058); National Natural Science Foundation of China(21975055); Guangdong Basic and Applied Basic Research Foundation(2019B1515120035); Guangdong Basic and Applied Basic Research Foundation(2021A1515010607)
Two thermally activated delayed fluorescence (TADF) red-emitting materials 3 and 4 with aggregation-induced emission (AIE) properties were designed and synthesized using benzothiazole-2-yl(phenyl)methanone as acceptors, and phenoxazine and phenothiazine with strong electron-donating ability as donors to construct donor-acceptor (D-A) type molecules, and their thermal stability, electrochemical properties, single crystal structure, photophysical properties and electroluminescence properties were systematically studied. The two compounds have small singlet-triplet slitting (ΔEST, 0.04 and 0.16 eV) and microsecond-scale delayed lifetimes (0.63 and 1.30 μs), showing obvious TADF characteristics. Comparing the emission spectra before and after grinding in the powder state, it is found that compound 4 has obvious mechanochromic luminescence phenomenon. In neat-film state, the emission peaks of the two compounds were 683 and 654 nm, and photoluminescence quantum yields (PLQYs) were 0.8% and 3.6%, respectively. The non-doped organic light-emitting diode (OLED) devices based on compounds 3 and 4 obtained pure red emission (662 and 652 nm), and the maximum external quantum efficiencies (EQEs) of the devices were 0.15% and 0.34%, respectively. Although the luminous efficiencies of devices based on these two compounds are not high, their synthesis process is facile, which can provide useful insight for the development of red TADF materials based on benzothiazolyl ketones.
Yuehua Zhang , Fei Nie , Lu Zhou , Xiaofeng Wang , Yuan Liu , Yanping Huo , Wencheng Chen , Zujin Zhao . Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones[J]. Chinese Journal of Organic Chemistry, 2023 , 43(11) : 3876 -3887 . DOI: 10.6023/cjoc202303022
| [1] | Zhou, J.; Tian, X. Y.; Wang, B. K.; Zhang, S. S.; Liu, Z. H.; Chen, W. Acta Chim. Sinica 2022, 80, 395. (in Chinese) |
| [1] | (周静, 田雪迎, 王斌凯, 张沙沙, 刘宗豪, 陈炜, 化学学报, 2022, 80, 395.) |
| [2] | Liang, Z. P.; Tang, R.; Qiu, Y. C.; Wang, Y.; Lu, H.; Wu, Z. G. Acta Chim. Sinica 2021, 79, 1401. (in Chinese) |
| [2] | (梁志鹏, 唐瑞, 邱雨晨, 王阳, 陆洪彬, 吴正光, 化学学报, 2021, 79, 1401.) |
| [3] | Sun, N.; Jiang, C.; Li, Q.; Tan, D.; Bi, S.; Song, J. J. Mater. Sci.: Mater. Electron. 2020, 31, 20688. |
| [4] | Yang, X.; Jiao, B.; Dang, J. S.; Sun, Y.; Wu, Y.; Zhou, G.; Wong, W. Y. ACS Appl. Mater. Interfaces 2018, 10, 10227. |
| [5] | Wong, M. Y.; Zysman-Colman, E. Adv. Mater. 2017, 29, 1605444. |
| [6] | Tao, Y.; Yuan, K.; Chen, T.; Xu, P.; Li, H. H.; Chen, R. F.; Zheng, C.; Zhang, L.; Huang, W. Adv. Mater. 2014, 26: 7931. |
| [7] | Di, B. H.; Chen, Y. L. Chin. Chem. Lett. 2018, 29, 245. |
| [8] | Huang, C.; Qiu, Z. P.; Gao, Y.; Chen, W. C.; Ji, S. M.; Huo, Y. P. Chin. J. Org. Chem. 2021, 41, 3050. (in Chinese) |
| [8] | (黄酬, 邱志鹏, 高杨, 陈文铖, 籍少敏, 霍延平, 有机化学, 2021, 41, 3050.) |
| [9] | 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) |
| [9] | (谭继华, 霍延平, 蔡宁, 籍少敏, 李宗植, 张力, 有机化学, 2017, 37, 2457.) |
| [10] | Sarada, G.; Cho, W.; Maheshwaran, A.; Sree, V. G.; Park, H. Y.; Gal, Y. S.; Song, M.; Jin, S. H. Adv. Funct. Mater. 2017, 27, 1701002. |
| [11] | Zheng, Y. T.; Zuo, L. Q.; Zhang, L. T.; Huang, Z. H.; Li, S. F.; Yang, Z.; Mao, Z.; Luo, S. L.; Liu, C.; Sun, F. Q.; Shi, G.; Chi, Z. G.; Xu, B. J. Chin. Chem. Lett. 2022, 33, 4536. |
| [12] | Cao, H. T.; Hou, P. F.; Cao, Q.; Li, Y. A.; Wang, S. S.; Xie, L. H. Acta Chim. Sinica 2022, 80, 1476. (in Chinese) |
| [12] | (曹洪涛, 侯鹏飞, 曹庆, 李延昂, 汪莎莎, 解令海, 化学学报, 2022, 80, 1476.) |
| [13] | Shi, Q.; Wang, L. Y. Chin. J. Org. Chem. 2022, 42, 1256. (in Chinese) |
| [13] | (石强, 王乐勇, 有机化学, 2022, 42, 1256.) |
| [14] | Guo, J. J.; Zhao, Z. J.; Tang, B. Z. Adv. Opt. Mater. 2018, 6, 1800264. |
| [15] | Sagara, Y.; Shizu, K.; Tanaka, H.; Miyazaki, H.; Goushi, K.; Kaji, H.; Adachi, C. Chem. Lett. 2015, 44, 360. |
| [16] | Ahn, D. H.; Kim, S. W.; Lee, H.; Ko, I. J.; Karthik, D.; Lee, J. Y.; Kwon, J. H. Nat. Photonics 2019, 13, 540. |
| [17] | Wu, T. L.; Huang, M. J.; Lin, C. C.; Huang, P. Y.; Chou, T. Y.; Chen-Cheng, R. W.; Lin, H. W.; Liu, R. S.; Cheng, C. H. Nat. Photonics 2018, 12, 235. |
| [18] | Bryden, M. A.; Zysman-Colman, E. Chem. Soc. Rev. 2021, 50, 7587. |
| [19] | Zhang, T.; Zhou, Z.; Liu, X.; Wang, K.; Fan, Y.; Zhang, C.; Yao, J.; Yan, Y.; Zhao, Y. S. J. Am. Chem. Soc. 2021, 143, 20249. |
| [20] | Steinegger, A.; Klimant, I.; Borisov, S. M. Adv. Opt. Mater. 2017, 5, 1700372. |
| [21] | Wong, M. Y.; Zysman-Colman, E. Adv. Mater. 2017, 29, 1605444. |
| [22] | Fang, F.; Yuan, Y.; Wan, Y.; Li, J.; Song, Y.; Chen, W.; Zhao, D.; Chi, Y.; Li, M.; Lee, C. Small 2022, 18, 2106215. |
| [23] | Fang, F.; Zhu, L.; Li, M.; Song, Y. Y.; Sun, M.; Zhao, D. G.; Zhang, J. F. Adv. Sci. 2021, 8, 2102970. |
| [24] | Tan, J. M.; Yu, Y. J.; Guan, M.; Zhao, Y. H.; Tang, Z. L.; Zhou, Z. H.; Guo, T. Chin. J. Org. Chem. 2022, 42, 3776. (in Chinese) |
| [24] | (谭佳敏, 余雅君, 关猛, 赵云辉, 唐子龙, 周智华, 郭涛, 有机化学, 2022, 42, 3776.) |
| [25] | Zeng, W.; Lin, M. H.; Zhu, L. Y.; Lin, M. J. Chin. J. Chem. 2022, 40, 39. |
| [26] | Ma, H.; Peng, Q.; An, Z.; Huang, W.; Shuai, Z. J. Am. Chem. Soc. 2018, 141, 1010. |
| [27] | Ma, R.; Ding, Y.; Chen, R.; Wang, Z.; Ma, Y. J. Org. Chem. 2020, 86, 310. |
| [28] | Okazaki, M.; Takeda, Y.; Data, P.; Pander, P.; Higginbotham, H.; Monkman, A. P.; Minakata, S. Chem. Sci. 2017, 8, 2677. |
| [29] | Huang, B.; Chen, W. C.; Li, Z. J.; Zhang, J. F.; Zhao, W. J.; Feng, Y.; Tang, B. Z.; Lee, C. S. Angew. Chem., Int. Ed. 2018, 57, 12473. |
| [30] | Xu, B. J.; Mu, Y. X.; Mao, Z.; Xie, Z. L.; Wu, H. Z.; Zhang, Y.; Jin, C. J.; Chi, Z. G.; Liu, S. W.; Xu, J. R.; Wu, Y. C.; Lu, P. Y.; Lien, A.; Bryce, M. R. Chem. Sci. 2016, 7, 2201. |
| [31] | Han, M.; Chen, Y.; Xie, Y.; Zhang, F.; Li, Z. Cell Rep. Phys. Sci. 2020, 1, 100252. |
| [32] | Borowicz, P.; Herbich, J.; Kapturkiewicz, A.; Opallo, M.; Nowacki, J. Chem. Phys. 1999, 249, 49. |
| [33] | Li, S. S.; Huang, X.; Gao, Y. L.; Jin, J. Org. Lett. 2022, 24, 5817. |
| [34] | Acar, N.; Kurzawa, J.; Fritz, N.; Stockmann, A.; Roman, C.; Schneider, S.; Clark, T. J. Phys. Chem. A 2003, 107, 9530. |
| [35] | Polgar, A. M.; Poisson, J.; Paisley, N. R.; Christopherson, C. J.; Reyes, A. C.; Hudson, Z. M. Macromolecules 2020, 53, 2039. |
/
| 〈 |
|
〉 |
