Citation: Hao Zhuo, Ming Zhang, Hengyuan Zhang, Hui Lin, Gang Yang, Silu Tao, Caijun Zheng, Xiaohong Zhang. Modified triphenylamine donors with shallower HOMO energy levels to construct long-wavelength TADF emitters of efficient organic light-emitting diodes[J]. Chinese Chemical Letters, ;2025, 36(5): 110760. doi: 10.1016/j.cclet.2024.110760 shu

Modified triphenylamine donors with shallower HOMO energy levels to construct long-wavelength TADF emitters of efficient organic light-emitting diodes

Hao Zhuo ^a ,
Ming Zhang ^a ,
Hengyuan Zhang ^a ,
Hui Lin ^a ,
Gang Yang ^a ,
Silu Tao ^a ,
Caijun Zheng ^{a, *,} ,
Xiaohong Zhang ^b

a.
School of Optoelectronic Science and Engineering, University of Electronic Science and Technology of China, Chengdu 610054, China
b.
Institute of Functional Nano & Soft Materials (FUNSOM), Soochow University, Suzhou 215123, China

zhengcaijun@uestc.edu.cn

Received Date: 25 September 2024
Revised Date: 9 December 2024
Accepted Date: 12 December 2024
Available Online: 13 December 2024

Figures(3)

Triphenylamine (TPA) is the most promising donor fragment for the construction of long-wavelength thermally activated delayed fluorescence (TADF) emitters owing to its suitable dihedral angle that could enhance radiative decay to compete with the serious non-radiative decay. However, the moderate electron-donating capacity of TPA seriously limits the selection of acceptor for constructing long-wavelength TADF emitters with narrow bandgaps. To address this issue, in this work, the peripheral benzene of TPA was replaced with 1,4-benzodioxane and anisole to obtain two new electron-donating units N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-phenyl-2,3-dihydrobenzo[b][1,4]dioxin-6-amine (TPADBO, −5.02 eV) and 4-methoxy-N-(4-methoxyphenyl)-N-phenylaniline (TPAMO, −5.00 eV), which possess much shallower highest occupied molecule orbital (HOMO) energy levels than the prototype TPA (−5.33 eV). Based on TPA and the modified TPA donor fragments, three TADF emitters were designed and synthesized, namely Py-TPA, Py-TPADBO and Py-TPAMO, with the same acceptor fragment 12-(2,6-diisopropylphenyl)pyrido[2′,3′:5,6]pyrazino[2,3-f][1,10]phenanthroline (Py). Among them, Py-TPAMO exhibits the highest photoluminescence quantum yield of 78.4% and the smallest singlet-triplet energy gap, which is because the introduction of anisole does not cause significant molecule deformation for the excited Py-TPAMO. And Py-TPAMO-based OLEDs successfully realize a maximum external quantum efficiency of 25.5% with the emission peak at 605 nm. This work provides a series of candidate of donor fragments for the development of efficient long-wavelength TADF emitters.
- Organic light-emitting diodes,
- Thermally activated delayed fluorescence,
- Long-wavelength emission,
- Triphenylamine,
- Shallow HOMO energy level
1. [1]
  G. Qian, Z.Y. Wang, Chem. Asian J. 5 (2010) 1006–1029. doi: 10.1002/asia.200900596
2. [2]
  A. Zampetti, A. Minotto, F. Cacialli, Adv. Funct. Mater. 29 (2019) 1807623. doi: 10.1002/adfm.201807623
3. [3]
  M. Xu, X. Li, S. Liu, L. Zhang, W. Xie, Mater. Chem. Front. 7 (2023) 4744–4767. doi: 10.1039/D3QM00585B
4. [4]
  M.P. Zhuo, X.D. Wang, L.S. Liao, Small Sci. 2 (2022) 2200029. doi: 10.1002/smsc.202200029
5. [5]
  Y. Li, J.Y. Liu, Y.D. Zhao, Y.C. Cao, Mater. Today 20 (2017) 258–266. doi: 10.1016/j.mattod.2016.12.003
6. [6]
  H. Xiang, J. Cheng, X. Ma, X. Zhou, J.J. Chruma, Chem. Soc. Rev. 42 (2013) 6128–6185. doi: 10.1039/c3cs60029g
7. [7]
  A. Minotto, I. Bulut, A.G. Rapidis, et al., Light: Sci. Appl. 10 (2021) 18. doi: 10.1038/s41377-020-00456-8
8. [8]
  C. Wu, Y. Zhang, J. Miao, et al., Chin. Chem. Lett. 34 (2023) 107445. doi: 10.1016/j.cclet.2022.04.043
9. [9]
  M. Zhang, C.J. Zheng, K. Wang, et al., Adv. Funct. Mater. 31 (2021) 2010100. doi: 10.1002/adfm.202010100
10. [10]
  Y. Zhang, D. Zhang, T. Huang, et al., Angew. Chem. Int. Ed. 60 (2021) 20498–20503. doi: 10.1002/anie.202107848
11. [11]
  H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 492 (2012) 234–238. doi: 10.1038/nature11687
12. [12]
  H. Kaji, H. Suzuki, T. Fukushima, et al., Nat. Commun. 6 (2015) 8476. doi: 10.1038/ncomms9476
13. [13]
  H.Y. Yang, H.Y. Zhang, M. Zhang, et al., Chem. Eng. J. 448 (2022) 137717. doi: 10.1016/j.cej.2022.137717
14. [14]
  M. Zhang, W. Liu, C.J. Zheng, et al., Adv. Sci. 6 (2019) 1801938. doi: 10.1002/advs.201801938
15. [15]
  M. Zhang, G. Dai, C. Zheng, et al., Chin. Chem. Lett. 33 (2022) 1110–1115. doi: 10.1016/j.cclet.2021.08.064
16. [16]
  M. Zhang, C.J. Zheng, H. Lin, S.L. Tao, Mater. Horiz. 8 (2021) 401–425. doi: 10.1039/D0MH01245A
17. [17]
  Z.Q. Wang, W. Liu, C. Xu, et al., Opt. Mater. 58 (2016) 260–267. doi: 10.1016/j.optmat.2016.05.053
18. [18]
  Z.Q. Wang, C.L. Liu, C.J. Zheng, et al., Org. Electron. 23 (2015) 179–185. doi: 10.1016/j.orgel.2015.04.024
19. [19]
  H.Y. Yang, H.Y. Zhang, M. Zhang, et al., Chem. Eng. J. 468 (2023) 143721. doi: 10.1016/j.cej.2023.143721
20. [20]
  Y. Xiao, H. Wang, Z. Xie, et al., Chem. Sci. 13 (2022) 8906–8923. doi: 10.1039/D2SC02201J
21. [21]
  J.V. Caspar, E.M. Kober, B.P. Sullivan, T.J. Meyer, J. Am. Chem. Soc. 104 (1982) 630–632. doi: 10.1021/ja00366a051
22. [22]
  H.C. Li, X. Tang, S.Y. Yang, et al., Chin. Chem. Lett. 32 (2021) 1245–1248. doi: 10.1016/j.cclet.2020.08.045
23. [23]
  J.H. Kim, J.H. Yun, J.Y. Lee, Adv. Opt. Mater. 6 (2018) 1800255. doi: 10.1002/adom.201800255
24. [24]
  J.L. He, F.C. Kong, B. Sun, et al., Chem. Eng. J. 424 (2021) 130470. doi: 10.1016/j.cej.2021.130470
25. [25]
  Y. Shen, X. Tang, Y. Xu, et al., Chin. Chem. Lett. 30 (2019) 1947–1950. doi: 10.1016/j.cclet.2019.07.059
26. [26]
  X. Hu, Y. Qin, Z. Li, et al., Chin. Chem. Lett. 33 (2022) 4645–4648. doi: 10.1016/j.cclet.2021.12.047
27. [27]
  X. Cao, D. Zhang, S. Zhang, Y. Tao, W. Huang, J. Mater. Chem. C 5 (2017) 7699–7714. doi: 10.1039/C7TC02481A
28. [28]
  W. Yang, W. Ning, H. Jungchi, et al., Chem. Eng. J. 438 (2022) 135571. doi: 10.1016/j.cej.2022.135571
29. [29]
  J. Xue, Q. Liang, R. Wang, et al., Adv. Mater. 31 (2019) 1808242. doi: 10.1002/adma.201808242
30. [30]
  J.X. Chen, H. Wang, Y.F. Xiao, et al., Small 18 (2022) 2201548. doi: 10.1002/smll.202201548
31. [31]
  Z. Cai, X. Wu, H. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 23635–23640. doi: 10.1002/anie.202111172
32. [32]
  S. Wang, Z. Cheng, X. Song, et al., ACS Appl. Mater. Interfaces 9 (2017) 9892–9901. doi: 10.1021/acsami.6b14796
33. [33]
  S.H. Kim, J. Choi, C. Sakong, et al., Dyes Pigm. 113 (2015) 390–401. doi: 10.1016/j.dyepig.2014.09.014
34. [34]
  J. Xue, J. Xu, J. Ren, et al., Sci. China Chem. 64 (2021) 1786–1795. doi: 10.1007/s11426-021-1096-8
35. [35]
  H. Wang, K. Wang, J.X. Chen, et al., Adv. Funct. Mater. 33 (2023) 2304398. doi: 10.1002/adfm.202304398
36. [36]
  J. Xue, J. Xu, Q. Liang, et al., Adv. Funct. Mater. 33 (2023) 2301312. doi: 10.1002/adfm.202301312
37. [37]
  Y.J. Yu, Y. Hu, S.Y. Yang, et al., Angew. Chem. Int. Ed. 59 (2020) 21578–21584. doi: 10.1002/anie.202006197
38. [38]
  D.G. Congrave, B.H. Drummond, Q. Gu, et al., J. Mater. Chem. C 10 (2022) 4831–4836. doi: 10.1039/D1TC04753A
39. [39]
  H. Wang, J.X. Chen, L. Zhou, et al., Mater. Horiz. 10 (2023) 2997–3004. doi: 10.1039/D3MH00445G
40. [40]
  J. Fan, Y. Xu, N. Li, et al., J. Mater. Chem. C 10 (2022) 17059–17065. doi: 10.1039/D2TC03933H
41. [41]
  K. Sun, D. Liu, W. Tian, et al., J. Mater. Chem. C 8 (2020) 11850–11859. doi: 10.1039/D0TC02577A
42. [42]
  W. Yuan, D. Hu, M. Zhu, et al., Dyes Pigm. 191 (2021) 109395. doi: 10.1016/j.dyepig.2021.109395
43. [43]
  R. Lin, J. Liu, W. Xu, et al., Adv. Mater. 35 (2023) 2303212. doi: 10.1002/adma.202303212
44. [44]
  H.Y. Zhang, H.Y. Yang, M. Zhang, et al., Mater. Horiz. 9 (2022) 2425–2432. doi: 10.1039/D2MH00639A
45. [45]
  R. Ishimatsu, S. Matsunami, K. Shizu, et al., J. Mater. Chem. A 117 (2013) 5607–5612.
46. [46]
  W.C. Chen, B. Huang, S.F. Ni, et al., Adv. Funct. Mater. 29 (2019) 1903112. doi: 10.1002/adfm.201903112
47. [47]
  Y. Zhang, H.S. Pang, X.J. He, et al., J. Phys. Chem. C 124 (2020) 2782–2790. doi: 10.1021/acs.jpcc.9b10234
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