Citation: Wang Zhiqiang, Bai Meidan, Zhang Ming, Zhang Zhiqiang, Feng Xun, Zheng Caijun. Synthesis and Properties of Two Novel Thermally Activated Delayed Fluorescence Materials with 1, 3, 5-Tribenzoylbenzene as Electron-Acceptor[J]. Acta Chimica Sinica, ;2020, 78(2): 140-146. doi: 10.6023/A19100372 shu

Synthesis and Properties of Two Novel Thermally Activated Delayed Fluorescence Materials with 1, 3, 5-Tribenzoylbenzene as Electron-Acceptor

a.
College of Chemistry and Chemical Engineering and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471934
b.
School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China(UESTC), Chengdu 610054
c.
Department of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450001

Corresponding author: Wang Zhiqiang, wzq197811@lynu.edu.cn Zhang Zhiqiang, Zheng Caijun, zhengcaijun@uestc.edu.cn
Received Date: 16 October 2019
Available Online: 25 February 2019
Fund Project: the Henan Natural Science Foundation 182300410230Project supported by the National Natural Science Foundation of China (No. 51773029) and the Henan Natural Science Foundation (No. 182300410230)the National Natural Science Foundation of China 51773029

Figures(9)

Two thermally activated delayed fluorescence (TADF) materials TBP-DmCz and TBP-TmCz were successfully synthesized using 1, 3, 5-tribenzoylbenzene (TBP) as electron-acceptor, 1, 8-dimethylcarbazole (DmCz) and 1, 3, 6, 8-tetra-methylcarbazole (TmCz) as electron-donor, respectively. Thermal gravimetric analysis show that the thermal decomposition temperatures (T_d) are 479℃ for TBP-DmCz and 484℃ for TBP-TmCz and no glass transition was found for both materials during the differential scanning calorimetry investigations. The highest occupied molecular orbitals (HOMO) are confined on the carbazole unit, while the lowest unoccupied molecular orbitals (LUMO) are located on the 1, 3, 5-tribenzoylbenzene unit, and there is almost no overlap between HOMO and LUMO, which is the typical molecular orbital character of TADF materials. Meanwhile, TBP-DmCz and TBP-TmCz possess degenerated HOMO and LUMO, which would promote the radiative transitions as the transitions could take place from all degenerated LUMOs to HOMOs. The HOMO level of TBP-TmCz is obviously higher than that of TBP-DmCz due to increasing the number of methyl groups at the electron-donor carbazole, and the LUMO levels of TBP-DmCz and TBP-TmCz only show a small difference because these materials have the same electron-acceptor 1, 3, 5-tribenzoylbenzene. In toluene solution, these materials have very similar absorption spectra and exhibit absorption bands assigned to intramolecular charge-transfer transition. The spectral peaks are located at 488 nm for TBP-DmCz and 502 nm for TBP-TmCz, respectively, in toluene solution at room temperature. According to the fluorescence and phosphorescence spectra of these materials in 1, 3-bis(N-carbazolyl)benzene (mCP) film at 77 K, the energy gaps between the lowest singlet and triplet (ΔE_ST) of TBP-DmCz and TBP-TmCz are calculated to be 0.05 and 0.01 eV, respectively. The fluorescence decay behaviors at different temperatures (100, 200 and 300 K) proved that emissions of TBP-DmCz and TBP-TmCz contain TADF component. The electroluminescence devices with TBP-DmCz and TBP-TmCz as the emitters show high efficiency and low efficiency roll-off. The maximum external quantum efficiencies of devices based on TBP-DmCz and TBP-TmCz are 13.6% and 18.3%, respectively.
- electroluminescence,
- light-emitting material,
- thermally activated delayed fluorescence,
- 1, 3, 5-tribenzoylbenzene,
- carbazole
1. [1]
  Sun, Y. R.; Giebink, N. C.; Kanno, H.; Ma, B. W.; Thompson, M. E.; Forrest, S. R. Nature 2006, 440, 908.
2. [2]
  Reineke, S.; Lindner, F.; Schwartz, G.; Seidler, N.; Walzer, K.; Lussem, B.; Leo, K. Nature 2009, 459, 234.
3. [3]
  Helander, M. G.; Wang, Z. B.; Qiu, J.; Greiner, M. T.; Puzzo, D. P.; Liu, Z. W. Science 2011, 332, 944.
4. [4]
  Han, T.-H.; Lee, Y.; Choi, M.-R.; Woo, S.-H.; Hong, B. H.; Ahn, J.-H.; Lee, T.-W. Nat. Photonics 2012, 459, 105.
5. [5]
  Sasabe, H.; Kido, J. J. Mater. Chem. C 2013, 1, 1699.
6. [6]
  Chen, S.; Dai, J.; Zhou, K.; Luo, Y.; Su, S.; Pu, X.; Huang, Y.; Lu, Z. Acta Chim. Sinica 2017, 75, 367.
7. [7]
  Qiu, Z.; Tan, J.; Cai, N.; Wang, K.; Ji, S.; Huo, Y. Chin. J. Org. Chem. 2019, 39, 679.
8. [8]
  He, X.; Xiao, Y.; Yuan, X.; Ye, S.; Jiang, H. Chin. J. Org. Chem. 2019, 39, 761.
9. [9]
  Wang, F.; Cao, X.; Mei, L.; Zhang, X.; Hu, J.; Tao, Y. Chin. J. Chem. 2018, 36, 241.
10. [10]
  Zhou, W.; Liu, Z.; Wang, Z.; Hu, S.; Liang, A. Chin. J. Org. Chem. 2019, 39, 1214.
11. [11]
  Xu, H.; Chen, R.; Sun, Q.; Huang, W.; Liu, X. Chem. Soc. Rev. 2014, 43, 3259.
12. [12]
  Volz, D.; Wallesch, M.; Fléchon, C.; Danz, M.; Verma, A.; Navarro, J. M.; Zink, D. M.; Bräse, S.; Baumann, T. Green Chem. 2015, 17, 1988.
13. [13]
  Chi, Y.; Tong, B.; Chou, P.-T. Coord. Chem. Rev. 2014, 281, 1.
14. [14]
  Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234.
15. [15]
  Dias, F. B.; Bourdakos, K. N.; Jankus, V.; Moss, K. C.; Kamtekar, K. T.; Bhalla, V.; Santos, J.; Bryce, M. R.; Monkman, A. P. Adv. Mater. 2013, 25, 3707.
16. [16]
  Zhang, D. D.; Duan, L. A.; Li, Y. L.; Zhang, D. Q.; Qiu, Y. J. Mater. Chem. C 2014, 2, 8191.
17. [17]
  Wang, H.; Xie, L.; Peng, Q.; Meng, L.; Wang, Y.; Yi, Y.; Wang, P. Adv. Mater. 2014, 26, 5198.
18. [18]
  Mei, L.; Hu, J.; Cao, X.; Wang, F.; Zheng, C.; Tao, Y.; Zhang, X.; Huang, W. Chem. Commun. 2015, 51, 13024.
19. [19]
  Cai, X.; Li, X.; Xie, G.; He, Z.; Gao, K.; Liu, K.; Chen, D.; Cao, Y.; Su, S. J. Chem. Sci. 2016, 7, 4264.
20. [20]
  Meng, L.; Wang, H.; Wei, X.; Liu, J.; Chen, Y.; Kong, X.; Lv, X.; Wang, P.; Wang, Y. ACS Appl. Mater. Interfaces 2016, 8, 20955.
21. [21]
  Wang, K.; Zheng, C. J.; Liu, W.; Liang, K.; Shi, Y. Z.; Tao, S. L.; Lee, C. S.; Ou, X. M.; Zhang, X. H. Adv. Mater. 2017, 29, 1701476.
22. [22]
  Lee, J.; Aizawa, N.; Yasuda, T. Chem. Mater. 2017, 29, 8012.
23. [23]
  Shi, Y. Z.; Wang, K.; Li, X.; Dai, G. L.; Liu, W.; Ke, K.; Zhang, M.; Tao, S. L.; Zheng, C. J.; Ou, X. M.; Zhang, X. H. Angew. Chem., Int. Ed. 2018, 57, 9480.
24. [24]
  Yu, L.; Wu, Z.; Xie, G.; Zeng, W.; Ma, D.; Yang, C. Chem. Sci. 2018, 9, 1385.
25. [25]
  Yang, Z.; Mao, Z.; Xu, C.; Chen, X.; Zhao, J.; Yang, Z.; Zhang, Y.; Wu, W.; Jiao, S.; Liu, Y.; Aldred, M. P.; Chi, Z. Chem. Sci. 2019, 10, 8129.
26. [26]
  Zhang, M.; Liu, W.; Zheng, C. J.; Wang, K.; Shi, Y. Z.; Li, X.; Lin, H.; Tao, S. L.; Zhang, X. H. Adv. Sci. 2019, 6, 1801938.
27. [27]
  Rajamalli, P.; Senthilkumar, N.; Gandeepan, P.; Huang, P. Y.; Huang, M. J.; Ren-Wu, C. Z.; Yang, C. Y.; Chiu, M. J.; Chu, L. K.; Lin, H. W.; Cheng, C. H. J. Am. Chem. Soc. 2016, 138, 628.
28. [28]
  Xie, Z.; Chen, C.; Xu, S.; Li, J.; Zhang, Y.; Liu, S.; Xu, J.; Chi, Z. Angew. Chem., Int. Ed. 2015, 54, 7181.
29. [29]
  Nikolaenko, A. E.; Cass, M.; Bourcet, F.; Mohamad, D.; Roberts, M. Adv. Mater. 2015, 27, 7236.
30. [30]
  Di, D.; Romanov, A. S.; Yang, L.; Richter, J. M.; Rivett, J. P. H.; Jones, S.; Thomas, T. H.; Jalebi, M. A.; Friend, R. H.; Linnolahti, M.; Bochmann, M.; Credgington, D. Science 2017, 356, 159.
31. [31]
  Wang, Z.; Zheng, C.; Wang, W.; Xu, C.; Ji, B.; Zhang, X. Inorg. Chem. 2016, 55, 2157.
32. [32]
  Wang, Z.; Sun, X.; Xu, C.; Ji, B. Front. Chem. 2019, DOI:10. 3389/fchem. 2019.00422 doi: 10.3389/fchem.2019.00422
33. [33]
  Song, X.; Zhang, D.; Lu, Y.; Yin, C.; Duan, L. Adv. Mater. 2019, 31, 1901923.
34. [34]
  Kretzschmar, A.; Patze, C.; Schwaebel, S. T.; Bunz, U. H. F. J. Org. Chem. 2015, 80, 9126.
35. [35]
  Zhu, Y.; Zhang, Y.; Yao, B.; Wang, Y.; Zhang, Z.; Zhan, H.; Zhang, B.; Xie, Z.; Wang, Y.; Cheng, Y. Macromolecules 2016, 49, 4373.
36. [36]
  Wang, Z.; Cai, J.; Zhang, M.; Zheng, C.; Ji, B. Acta Chim. Sinica 2019, 77, 263.
37. [37]
  Yang, Z.; Mao, Z.; Xie, Z.; Zhang, Y.; Liu, S.; Zhao, J.; Xu, J.; Chi Z.; Aldred, M. P. Chem. Soc. Rev. 2017, 46, 915.
38. [38]
  Huang, T.; Jiang, W.; Duan, L. J. Mater. Chem. C 2018, 6, 5577.
39. [39]
  Godumala, M.; Choi, S.; Cho, M. J.; Choi, D. H. J. Mater. Chem. C 2019, 7, 2172.
40. [40]
  Cao, X.; Zhang, D.; Zhang, S.; Tao, Y.; Huang, W. J. Mater. Chem. C 2017, 5, 7699.
41. [41]
  Godumala, M.; Choi, S.; Cho, M. J.; Choi, D. H. J. Mater. Chem. C 2016, 4, 11355.
42. [42]
  Cai, X.; Chen, D.; Gao, K.; Gan, L.; Yin, Q.; Qiao, Z.; Chen, Z.; Jiang, X.; Su, S.-J. Adv. Funct. Mater. 2017, 27, 1704927.
43. [43]
  Bai, M.-D.; Zhang, M.; Wang, K.; Shi, Y.-Z.; Chen, J.-X.; Lin, H.; Tao, S.-L.; Zheng, C.-J.; Zhang, X.-H. Org. Electron. 2018, 62, 220.
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