ARTICLES

Construction of Blue Thermally Activated Delayed Fluorescence Materials Based on the Heptagonal Triarylamine Donor

  • Zhi Li ,
  • Zhenlong Li ,
  • Junjie Liu ,
  • Weiguo Han ,
  • Jingsong You ,
  • Zhengyang Bin
Expand
  • College of Chemistry, Sichuan University, Chengdu 610065

Received date: 2023-12-07

  Revised date: 2024-01-23

  Online published: 2024-02-20

Supported by

National Natural Science Foundation of China(22275127)

Abstract

The development of efficient blue light-emitting materials is a crucial yet challenging task in organic light-emitting diodes (OLED). Two novel blue light-emitting molecules, TRZCz-TPA and TRZ-TPA, have been designed and synthesized based on the heptagonal 9H-tripheno[b,d,f]nitrozoafluorene (TPA) donor. Their thermal stability, electrochemical properties, photophysical properties, and device performances were characterized. TRZCz-TPA and TRZ-TPA both exhibit blue emission in toluene solution with emission peaks at 455 and 440 nm, respectively. In contrast to TRZ-TPA, which exhibits through-bond charge transfer (TBCT) from the TPA donor to the diphenyltriazine (TRZ) acceptor, TRZCz-TPA, featuring two adjacent 3,6-di-tert-butylcarbazole (tBuCz) donors near the TRZ acceptor, demonstrates through-space charge transfer (TSCT) from the tBuCz donors to the TRZ acceptor. This leads to a remarkable reduction in the singlet-triplet energy gap (ΔEST) from 0.53 eV to 0.04 eV, thereby displaying thermally activated delayed fluorescence (TADF) properties. Additionally, tBuCz donor with large steric hindrance effectively suppresses aggregation-induced quenching in the aggregated state. Consequently, TRZCz-TPA achieves a photoluminescence quantum yield (PLQY) of 42.0% and a maximum external quantum efficiency (EQEmax) of 10.4% in OLED devices, significantly outperforming TRZ-TPA (PLQY=6.5%, EQEmax=3.7%).

Cite this article

Zhi Li , Zhenlong Li , Junjie Liu , Weiguo Han , Jingsong You , Zhengyang Bin . Construction of Blue Thermally Activated Delayed Fluorescence Materials Based on the Heptagonal Triarylamine Donor[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 2006 -2013 . DOI: 10.6023/cjoc202312006

References

[1]
Adachi, C. Jpn. J. Appl. Phys. 2014, 53, 060101.
[2]
Chaskar, A.; Chen, H.-F.; Wong, K.-T. Adv. Mater. 2011, 23, 3876.
[3]
Wong, M. Y.; Zysman-Colman, E. Adv. Mater. 2017, 29, 1605444.
[4]
Wu, Y.; Zhang, Z.; Yue, S.; Huang, R.; Du, H.; Zhao, Y. Chin. J. Chem. 2015, 33, 897.
[5]
Li, B. Chin. J. Org. Chem. 2015, 35, 2487. (in Chinese)
[5]
(李保林, 有机化学, 2015, 35, 2487.)
[6]
Tao, Y.; Yuan, K.; Chen, T.; Xu, P.; Li, H.; Chen, R.; Zheng, C.; Zhang, L.; Huang, W. Adv. Mater. 2014, 26, 7931.
[7]
Yang, X.; Jiao, B.; Dang, J.-S.; Sun, Y.; Wu, Y.; Zhou, G.; Wong, W.-Y. ACS Appl. Mater. Interfaces 2018, 10, 10227.
[8]
Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395, 151.
[9]
Huang, C.; Qiu, Z.; Gao, Y.; Chen, W.; Ji, S.; Huo, Y. Chin. J. Org. Chem. 2021, 41, 3050. (in Chinese)
[9]
(黄酬, 邱志鹏, 高杨, 陈文铖, 籍少敏, 霍延平, 有机化学, 2021, 41, 3050).
[10]
Park, Y.-S.; Lee, S.; Kim, K.-H.; Kim, S.-Y.; Lee, J.-H.; Kim, J.-J. Adv. Funct. Mater. 2013, 23, 4914.
[11]
Wang, Q.; Oswald, I. W. H.; Yang, X.; Zhou, G.; Jia, H.; Qiao, Q.; Chen, Y.; Hoshikawa-Halbert, J.; Gnade, B. E. Adv. Mater. 2014, 26, 8107.
[12]
Goushi, K.; Yoshida, K.; Sato, K.; Adachi, C. Nat. Photonics 2012, 6, 253.
[13]
Wang, T; Hua, X; Yu, Y; Yuan, Y; Feng, M; Jiang, Z. Chin. J. Org. Chem. 2019, 39, 1436. (in Chinese)
[13]
(王彤彤, 华晓晨, 郁友军, 袁熠, 冯敏强, 蒋佐权, 有机化学, 2019, 39, 1436).
[14]
Endo, A.; Sato, K.; Yoshimura, K.; Kai, T.; Kawada, A.; Miyazaki, H.; Adachi, C. Appl. Phys. Lett. 2011, 98, 083302.
[15]
Huang, Z.; Yang, D.; Ma, D.; Bin, Z.; You, J. Sci. China Chem. 2024, 67, 1181.
[16]
Shi, Q; Wang, L. Chin. J. Org. Chem. 2022, 42, 1256. (in Chinese)
[16]
(石强, 王乐勇, 有机化学, 2022, 42, 1256.)
[17]
Guo, J.; Zhao, Z.; Tang, B. Z. Adv. Opt. Mater. 2018, 6, 1800264.
[18]
Sagara, Y.; Shizu, K.; Tanaka, H.; Miyazaki, H.; Goushi, K.; Kaji, H.; Adachi, C. Chem. Lett. 2014, 44, 360.
[19]
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.
[20]
Lee, D. R.; Kim, M.; Jeon, S. K.; Hwang, S.-H.; Lee, C. W.; Lee, J. Y. Adv. Mater. 2015, 27, 5861.
[21]
Méhes, G.; Nomura, H.; Zhang, Q.; Nakagawa, T.; Adachi, C. Angew. Chem., Int. Ed. 2012, 51, 11311.
[22]
Liu, Y.; Xiao, X.; Huang, Z.; Yang, D.; Ma, D.; Liu, J.; Lei, B.; Bin, Z.; You, J. Angew. Chem., Int. Ed. 2022, 61, e202210210.
[23]
Liang, W.; Yang, Y.; Yang, M.; Zhang, M.; Li, C.; Ran, Y.; Lan, J.; Bin, Z.; You, J. Angew. Chem., Int. Ed. 2021, 60, 3493.
[24]
Liu, J.; Bin, Z.; Yang, D.; Ma, D.; You, J. Chem. Eng. J. 2023, 466, 142910.
[25]
Ma, W.; Bin, Z.; Yang, G.; Liu, J.; You, J. Angew. Chem., Int. Ed. 2022, 61, e202116681.
[26]
Huang, Z.; Bin, Z.; Su, R.; Yang, F.; Lan, J.; You, J. Angew. Chem., Int. Ed. 2020, 59, 9992.
[27]
Huang, Z.; Lei, B.; Yang, D.; Ma, D.; Bin, Z.; You, J. Angew. Chem., Int. Ed. 2022, 61, e202213157.
[28]
Xiao, X.; Lei, B.; Wu, D.; Bin, Z. Chem. Commun. 2023, 59, 6556.
[29]
Yang, S; Wang, Y; Peng, C; Wu, Z; Yuan, S; Yu, Y; Li, H; Wang, T; Li, H; Zheng, Y; Jiang, Z; Liao, L. J. Am. Chem. Soc. 2020, 142, 17756.
[30]
Zhao, Z.; Zeng, C.; Peng, X.; Liu, Y.; Zhao, H.; Hua, L.; Su, S.; Yan, S.; Ren, Z. Angew. Chem., Int. Ed. 2022, 61, e202210864.
[31]
Han, W.; Liu, J.; Ran, C.; Huang, Z.; Gao, G.; You, J.; Bin, Z. Angew. Chem., Int. Ed. 2023, e202312297.
[32]
Wang, X.; Xu, Y.; Yang, L.; Lu, X.; Zou, H.; Yang, W.; Zhang, Y.; Li, Z.; Ma, M. J. Fluoresc. 2018, 28, 707.
Outlines

/

〈 〉