Citation: Yu Jia, Xiao Yafang, Chen Jiaxiong. Design and Synthesis of Novel Red Thermally Activated Delayed Fluorescent Molecule Based on Acenaphtho[1, 2-b]quinoxaline Electron-Acceptor[J]. Chinese Journal of Organic Chemistry, ;2019, 39(12): 3460-3466. doi: 10.6023/cjoc201906019 shu

Design and Synthesis of Novel Red Thermally Activated Delayed Fluorescent Molecule Based on Acenaphtho[1, 2-b]quinoxaline Electron-Acceptor

a.
Institute of Functional Nano & Soft Materials (FUNSOM), Collaborative Innovation Center of Suzhou Nano Science and Technology, Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou 215123
b.
Department of Chemistry, City University of Hong Kong, Kowloon Tong, Hong Kong

Corresponding author: Chen Jiaxiong, chenjiaxiong@suda.edu.cn
Received Date: 17 June 2019
Revised Date: 22 July 2019
Available Online: 30 December 2019
Fund Project: Project supported by the China Postdoctoral Science Foundation (No. 2018M640517)the China Postdoctoral Science Foundation 2018M640517

Figures(8)

A new thermally activated delayed fluorescence (TADF) acceptor (A) segment, acenaphtho[1, 2-b]quinoxaline (AQ) group, is designed. And a novel red TADF material 10, 10', 10''-(acenaphtho[1, 2-b]quinoxaline-3, 9, 10-triyl)tris(10H-phenoxazine) (AQ-TPXZ) is developed by the conjunction of AQ group with phenoxazine as donor (D) moieties. The density functional theory calculation shows that this D-A molecule has a well separation between the highest occupied molecular orbital and the lowest unoccupied molecular orbital. And the energy splitting between the lowest singlet state and the lowest triplet state is calculated to be 0.02 eV. The transient photoluminescence decays of AQ-TPXZ doped 4, 4'-di(9H-carbazol-9-yl)-1, 1'-biphenyl film exhibit double-component emission decay profiles. The organic light-emitting diode (OLED) using AQ-TPXZ as dopant realizes red emission with a peak at 624 nm. Moreover, the device obtains maximum external quantum efficiency (EQE) up to 7.4%, which is higher than the theoretical maximum EQE (5%) of traditional fluorescent OLEDs. This result not only indicates that AQ-TPXZ is a red TADF material but also provides a newly electron acceptor segment for designing novel red TADF emitters.
- thermally activated delayed fluorescent,
- acenaphtho[1, 2-b]quinoxaline,
- phenoxazine,
- red emitter,
- organic light-emitting diode
1. [1]
  Tang, C. W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610. doi: 10.1063/1.343409
2. [2]
  Reineke, S.; Lindner, F.; Schwartz, G.; Seidler, N.; Walzer, K.; Lüssem, B.; Leo, K. Nature 2009, 459, 234. doi: 10.1038/nature08003
3. [3]
  Di, D.; Romanov, A. S.; Yang, L.; Richter, J. M.; Rivett, J. P. H.; Jones, S.; Thomas, T. H.; Abdi Jalebi, M.; Friend, R. H.; Linnolahti, M.; Bochmann, M.; Credgington, D. Science 2017, 356, 159. doi: 10.1126/science.aah4345
4. [4]
  Ye, Z.; Yang, J.; Ling, Z.; Zhao, Y.; Chen, G.; Zheng, Y.; Wei, B.; Shi, Y. Chin. J. Org. Chem. 2019, 39, 449(in Chinese).
5. [5]
  Xu, Y.; Liang, X.; Zhou, X.; Yuan, P.; Zhou, J.; Wang, C.; Li, B.; Hu, D.; Qiao, X.; Jiang, X.; Liu, L.; Su, S.; Ma, D.; Ma, Y. Adv. Mater. 2019, 31, 1807388. doi: 10.1002/adma.201807388
6. [6]
  Guo, F.; Karl, A.; Xue, Q.-F.; Tam, K. C.; Forberich, K.; Brabec, C. J. Light Sci. Appl. 2017, 6, e17094. doi: 10.1038/lsa.2017.94
7. [7]
  Lin, D.; Song, S.; Chen, Z.; Guo, P.; Chen, J.; Shi, H.; Mai, Y.; Song, H. Chin. J. Org. Chem. 2018, 38, 103(in Chinese).
8. [8]
  Kaji, H.; Suzuki, H.; Fukushima, T.; Shizu, K.; Suzuki, K.; Kubo, S.; Komino, T.; Oiwa, H.; Suzuki, F.; Wakamiya, A.; Murata, Y.; Adachi, C. Nat. Commun. 2015, 6, 8476. doi: 10.1038/ncomms9476
9. [9]
  Wang, Z.; Li, X.-L.; Ma, Z.; Cai, X.; Cai, C.; Su, S.-J. Adv. Funct. Mater. 2018, 28, 1706922. doi: 10.1002/adfm.201706922
10. [10]
  Chen, S.; Dai, J.; Zhou, K.; Luo, Y.; Su, S.; Pu, X.; Huang, Y.; Lu, Z. Acta Chim. Sin. 2017, 75, 367(in Chinese).
11. [11]
  Zhen, C.-G.; Dai, Y.-F.; Zeng, W.-J.; Ma, Z.; Chen, Z.-K.; Kieffer, J. Adv. Funct. Mater. 2011, 21, 699. doi: 10.1002/adfm.201002165
12. [12]
  Yuan, Y.; Chen, J.-X.; Chen, W.-C.; Ni, S.-F.; Wei, H.-X.; Ye, J.; Wong, F.-L.; Zhou, Z.-W.; Tong, Q.-X.; Lee, C.-S. Org. Electron. 2015, 18, 61. doi: 10.1016/j.orgel.2015.01.009
13. [13]
  Wu, Y.; Ren, H.; Wu, Y.; Wang, B. Acta Chim. Sin. 2015, 73, 53(in Chinese).
14. [14]
  Yang, X.; Jiao, B.; Dang, J.-S.; Sun, Y.; Wu, Y.; Zhou, G.; Wong, W.-Y. ACS Appl. Mater. Interfaces 2018, 10, 10227. doi: 10.1021/acsami.7b18330
15. [15]
  Li, X.; Zhang, J.; Zhao, Z.; Wang, L.; Yang, H.; Chang, Q.; Jiang, N.; Liu, Z.; Bian, Z.; Liu, W.; Lu, Z.; Huang, C. Adv. Mater. 2018, 30, 1705005. doi: 10.1002/adma.201705005
16. [16]
  Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395, 4.
17. [17]
  Chi, Y.; Tong, B.; Chou, P.-T. Coord. Chem. Rev. 2014, 281, 1. doi: 10.1016/j.ccr.2014.08.012
18. [18]
  Xu, H.; Chen, R.; Sun, Q.; Huang, W.; Liu, X. Chem. Soc. Rev. 2014, 43, 3259. doi: 10.1039/C3CS60449G
19. [19]
  Yang, X.; Guo, H.; Liu, B.; Zhao, J.; Zhou, G.; Wu, Z.; Wong, W.-Y. Adv. Sci. 2018, 5, 1701067. doi: 10.1002/advs.201701067
20. [20]
  Ai, X.; Evans, E. W.; Dong, S.; Gillett, A. J.; Guo, H.; Chen, Y.; Hele, T. J. H.; Friend, R. H.; Li, F. Nature 2018, 563, 536. doi: 10.1038/s41586-018-0695-9
21. [21]
  Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234. doi: 10.1038/nature11687
22. [22]
  Leitl, M. J.; Krylova, V. A.; Djurovich, P. I.; Thompson, M. E.; Yersin, H. J. Am. Chem. Soc. 2014, 136, 16032. doi: 10.1021/ja508155x
23. [23]
  Shao, S. Y.; Ding, J. Q.; Wang, L. X. Chin. J. Appl. Chem. 2018, 993(in Chinese). doi: 10.11944/j.issn.1000-0518.2018.09.180202
24. [24]
  Dias, F. B.; Santos, J.; Graves, D. R.; Data, P.; Nobuyasu, R. S.; Fox, M. A.; Batsanov, A. S.; Palmeira, T.; Berberan-Santos, M. N.; Bryce, M. R.; Monkman, A. P. Adv. Sci. 2016, 3, 1600080. doi: 10.1002/advs.201600080
25. [25]
  Chen, J.-X.; Liu, W.; Zheng, C.-J.; Wang, K.; Liang, K.; Shi, Y.-Z.; Ou, X.-M.; Zhang, X.-H. ACS Appl. Mater. Interfaces 2017, 9, 8848. doi: 10.1021/acsami.6b15816
26. [26]
  Godumala, M.; Choi, S.; Park, S. Y.; Cho, M. J.; Kim, H. J.; Ahn, D. H.; Moon, J. S.; Kwon, J. H.; Choi, D. H. Chem. Mater. 2018, 30, 5005. doi: 10.1021/acs.chemmater.8b01207
27. [27]
  Wang, T.-T, ; Huang, X. C.; Yu, Y. J.; Yuan, Y.; Feng, M. Q.; Jiang, Z. Q. Chin. J. Org. Chem. 2019, 39, 1436(in Chinese).
28. [28]
  Guo, X. G.; Feng, S. Y. Chem. Res. 2019, 30, 111(in Chinese).
29. [29]
  Chen, X.-L.; Jia, J.-H.; Yu, R.; Liao, J.-Z.; Yang, M.-X.; Lu, C.-Z. Angew. Chem. Int. Ed. 2017, 56, 15006. doi: 10.1002/anie.201709125
30. [30]
  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).
31. [31]
  Zhang, Q.; Li, B.; Huang, S.; Nomura, H.; Tanaka, H.; Adachi, C. Nat. Photonics 2014, 8, 326. doi: 10.1038/nphoton.2014.12
32. [32]
  Sun, J. W.; Lee, J.-H.; Moon, C.-K.; Kim, K.-H.; Shin, H.; Kim, J.-J. Adv. Mater. 2014, 26, 5684. doi: 10.1002/adma.201401407
33. [33]
  Pan, K.-C.; Li, S.-W.; Ho, Y.-Y.; Shiu, Y.-J.; Tsai, W.-L.; Jiao, M.; Lee, W.-K.; Wu, C.-C.; Chung, C.-L.; Chatterjee, T.; Li. Y.-S.; Wong, K.-T.; Hu, H.-C.; Chen, C.-C.; Lee, M.-T. Adv. Funct. Mater. 2016, 26, 7560. doi: 10.1002/adfm.201602501
34. [34]
  Lee, S. Y.; Yasuda, T.; Yang, Y. S.; Zhang, Q.; Adachi, C. Angew. Chem. Int. Ed. 2014, 53, 6402. doi: 10.1002/anie.201402992
35. [35]
  Hirata, S.; Sakai, Y.; Masui, K.; Tanaka, H.; Lee, S. Y.; Nomura, H.; Nakamura, N.; Yasumatsu, M.; Nakanotani, H.; Zhang, Q.; Shizu, K.; Miyazaki, H.; Adachi, C. Nat. Mater. 2015, 14, 330. doi: 10.1038/nmat4154
36. [36]
  Li, J.; Nakagawa, T.; MacDonald, J.; Zhang, Q.; Nomura, H.; Miyazaki, H.; Adachi, C. Adv. Mater. 2013, 25, 3319. doi: 10.1002/adma.201300575
37. [37]
  Zhang, Q.; Kuwabara, H.; Potscavage, W. J.; Huang, S.; Hatae, Y.; Shibata, T.; Adachi, C. J. Am. Chem. Soc. 2014, 136, 18070. doi: 10.1021/ja510144h
38. [38]
  Wang, S.; Cheng, Z.; Song, X.; Yan, X.; Ye, K.; Liu, Y.; Yang, G.; Wang, Y. ACS Appl. Mater. Interfaces 2017, 9, 9892. doi: 10.1021/acsami.6b14796
39. [39]
  Yuan, Y.; Hu, Y.; Zhang, Y.-X.; Lin, J.-D.; Wang, Y.-K.; Jiang, Z.-Q.; Liao, L.-S.; Lee, S.-T. Adv. Funct. Mater. 2017, 27, 1700986. doi: 10.1002/adfm.201700986
40. [40]
  Chen, J.-X.; Wang, K.; Zheng, C.-J.; Zhang, M.; Shi, Y.-Z.; Tao, S.-L.; Lin, H.; Liu, W.; Tao, W.-W.; Ou, X.-M.; Zhang, X.-H. Adv. Sci. 2018, 5, 1800436. doi: 10.1002/advs.201800436
41. [41]
  Yang, Y.; Zhao, L.; Wang, S. M.; Ding, J. Q.; Wang, L. X. Acta Polym. Sin. 2019, 50, 1(in Chinese).
42. [42]
  Yu, L.; Wu, Z.; Xie, G.; Zeng, W.; Ma, D.; Yang, C. Chem. Sci. 2018, 9, 1385. doi: 10.1039/C7SC04669C
43. [43]
  Yuan, Y.; Chen, J.-X.; Chen, W.-C.; Ni, S.-F.; Wei, H.-X.; Ye, J.; Wong, F.-L.; Zhou, Z.-W.; Tong, Q.-X.; Lee, C.-S. Org. Electron. 2015, 18, 61. doi: 10.1016/j.orgel.2015.01.009
44. [44]
  Chen, J.-X.; Liu, W.; Zheng, C.-J.; Wang, K.; Liang, K.; Shi, Y.-Z.; Ou, X.-M.; Zhang, X.-H. ACS Appl. Mater. Interfaces 2017, 9, 8848. doi: 10.1021/acsami.6b15816
45. [45]
  Park, I. S.; Lee, S. Y.; Adachi, C.; Yasuda, T. Adv. Funct. Mater. 2016, 26, 1813. doi: 10.1002/adfm.201505106
46. [46]
  Lee, S. Y.; Adachi, C.; Yasuda, T. Adv. Mater. 2016, 28, 4626. doi: 10.1002/adma.201506391
47. [47]
  Park, H.-J.; Han, S. H.; Lee, J. Y.; Han, H.; Kim, E.-G. Chem. Mater. 2018, 30, 3215. doi: 10.1021/acs.chemmater.8b00006
48. [48]
  Xie, G.; Li, X.; Chen, D.; Wang, Z.; Cai, X.; Chen, D.; Li, Y.; Liu, K.; Cao, Y.; Su, S.-J. Adv. Mater. 2016, 28, 181. doi: 10.1002/adma.201503225
49. [49]
  Zhang, D.; Song, X.; Cai, M.; Kaji, H.; Duan, L. Adv. Mater. 2018, 30, 1705406. doi: 10.1002/adma.201705406
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