SIOC 中文
ACS
Adv search

Acta Chimica Sinica >

0 25090323

DOI: https://doi.org/10.6023/A25090323

Article

Multiple Resonance Thermally Activated Delayed Fluorescence Molecule Based on 3, 6- Diphenylselenylcarbazole

  • 汪庆辉 ,
  • 任正 ,
  • 张凯 ,
  • 周东营 ,
  • 樊健
Expand
  • aState Key Laboratory of Bioinspired Interfacial Materials Science, Institute of Functional Nano & Soft Materials (FUNSOM), Soochow University, Suzhou 215123, China
    bCollege of Physics and Engineering, Qufu Normal University, Qufu, Shandong, 273165, China
    cState Key Laboratory of Structural Chemistry, Fujian Institute of Research on Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China

Received date: 2025-09-27

  Online published: 2025-11-11

Supported by

National Key R&D Program of China (No. 2020YFA0714604, 2024YFB3612102), the International Science and Technology Innovation Cooperation/Hong Kong, Macao and Taiwan Science and Technology Innovation Cooperation Project of Jiangsu Province, China (No. BZ2023053).

Fold

Abstract

Conventional multiple resonance thermally activated delayed fluorescence material (MR-TADF) has a narrow emission spectrum with full width at half maximum (FWHM) <30 nm due to its planar rigid structure that suppresses vibrational relaxation and thus makes devices with higher color purity, but it usually faces the problem of a low rate of reverse intersystem crossing (kRISC), and the device has a significant roll-off in efficiency at high luminance. Therefore, a molecule 2SetCzBN was designed and synthesized by introducing selenium atoms into the 3, 6 position of carbazole, which utilizes the heavy-atom effect of selenium to enhance the spin-orbit coupling effect of S1 and T1, accelerating the reverse intersystem crossing rate and thus decreasing the efficiency roll-off of the device at high luminance. The thermal decomposition temperature (temperature at 5% mass loss, Td) of the compound 2SetCzBN was 388 °C, proving that it can be sufficient to withstand the heat treatment procedures during device preparation. The FWHM of 2SetCzBN in dilute toluene solution is 26 nm and the ΔEST is only 0.14 eV. The prompt fluorescence lifetimes of 2SetCzBN film is 1.3 ns and the delayed fluorescence lifetime is 3.27 μs. The orbital distribution and geometric configuration of 2setczbn are simulated, and the molecule has a high oscillator strength (f) of 0.4577. Meanwhile, the S1 and T1 of 2SetCzBN are hybrid local charge transfer (HLCT) excited states, and the T2 energy level is mainly local excited states (LE). In addition, due to the influence of heavy atom effect, 2SetCzBN has a large spin-orbit coupling constant of 2.132 cm-1, and finally achieves a high reverse intersystem crossing rate (2.49 × 106 s-1). Remarkably, when 2SetCzBN was doped in the host material PhCzBCz with 15% (w) Firpic as the sensitizer, the OLED device achieves a maximum EQE of 27.6%, and 22.2% at 103 cd/m2. Furthermore, the maximum EQE can reach 31.3% with the optimal thickness of the electron-transport layer (50 nm).

Key words： thermally activated delayed fluorescence; heavy atom effect; multiple resonance effect; selenium; organic light-emitting diode

Cite this article

汪庆辉 , 任正 , 张凯 , 周东营 , 樊健 . Multiple Resonance Thermally Activated Delayed Fluorescence Molecule Based on 3, 6- Diphenylselenylcarbazole[J]. Acta Chimica Sinica, 0 : 25090323 . DOI: 10.6023/A25090323

References

[1] Joo W. J.; Kyoung J.; Esfandyarpour M.; Lee S. H.; Koo H.; Song S.; Kwon Y. N.; Song S. H.; Bae J. C.; Jo A.; Kwon M. J.; Han S. H.; Kim S. H.; Hwang S.; Brongersma M. L.Science. 2020, 370, 459.
[2] Ge F.-J.; Zhang K.-Z.; Cao Q.-P.; Xu H.; Zhou T.; Zhang W.-H.; Ban X.-X.; Zhang X.-B.; Li N.; Zhu P. Acta Chim. Sinica 2023, 81, 1157(in Chinese). (葛凤洁, 张开志, 曹清鹏, 徐慧, 周涛, 张文浩, 班鑫鑫, 张晓波, 李娜, 化学学报, 2023, 81, 1157.)
[3] Hsiang E. L.; Yang Z. Y.; Yang Q.; Lan Y. F.; Wu S. T.J. Soc. Inf. Disp. 2021, 29, 446.
[4] Huang Y. G.; Hsiang E. L.; Deng M. Y.; Wu S. T. Light Sci. Appl. 2020, 9, 105.
[5] Liu P.-Y.; Tang Z.-F.; Sun W.-D.Journal of Jinan University, 2002, 23, 66(in Chinese). (刘彭义, 唐振方, 孙汪典, 暨南大学学报, 2002, 23, 66.)
[6] Mukherjee S.; Thilagar P.Chem. Commun. 2015, 51, 10988.
[7] Zhang Q. S.; Li J.; Shizu K.; Huang S. P.; Hirata S.; Miyazaki H.; Adachi C.J. Am. Chem. Soc. 2012, 134, 14706.
[8] Zheng X.; Yang C.-L.Chinese Journal of Luminescence 2022, 43, 1027(in Chinese). (郑贤, 杨朝龙, 发光学报, 2022, 43, 1027.)
[9] Uoyama H.; Goushi K.; Shizu K.; Nomura H.; Adachi C.Nature. 2012, 492, 234.
[10] Luo X. F.; Xiao X. W.; Zheng Y. X.Chem. Commun. 2024, 60, 1089.
[11] Ma J.-Z.; Li Y.; Gao S.; Zhao Y.; Ding L.; Zhou D.-Y.; Fan J.Acta Chim. Sinica 2025, 83, 17(in Chinese). (马金珠, 李阳, 高珊, 赵越, 丁磊, 周东营, 樊健, 化学学报, 2025, 83, 17.)
[12] Zhang D.-C.; Jia J.-H.; Liang D.; Cai X.-B.; Zhao Y.-Q.; Hu X.-L.; Jiang Y.-B.; Lu C.-Z. Acta Chim. Sinica 2024, 82, 887(in Chinese). (张登朝, 贾吉慧, 梁栋, 蔡显宝, 赵雨晴, 胡祥龙, 江钰冰, 卢灿忠, 化学学报, 2024, 82, 883.)
[13] Fang S.-Q.; Tong K.-N.; Chen S.-H.; Zhang Q.-F.; Tong B.-H.; Feng M.-Q.; Kong H. Acta Chim. Sinica 2025, 83, 471(in Chinese). (方素琴, 童恺宁, 陈思浛, 张千峰, 童碧海, 冯敏强, 孔辉, 化学学报, 2025, 83, 471.)
[14] Jiang H.; Jin J.-B.; Chen R.-F.; Zheng C.; Huang W.Prog Chem 2016, 28, 1811(in Chinese). (姜贺, 靳继彪, 陈润锋, 郑超, 黄维, 化学进展, 2016, 28, 1811.)
[15] Wang Y.-N.; Shao S.-Y.; Wang L.-X.Acta Chim. Sinica 2023, 81, 1202(in Chinese). (王一诺, 邵世洋, 王利祥, 化学学报, 2023, 81, 1202.)
[16] Hatakeyama T.; Shiren K.; Nakajima K.; Nomura S.; Nakatsuka S.; Kinoshita K.; Ni J.; Ono Y.; Ikuta T.Adv. Mater. 2016, 28, 2777.
[17] Yuan W. B.; Jin Q.; Du M. X.; Duan L.; Zhang Y. W.Adv. Mater. 2024, 36, 2410096.
[18] Meng G. Y.; Dai H. Y.; Wang Q.; Zhou J. P.; Fan T. J.; Zeng X.; Wang X.; Zhang Y. W.; Yang D. Z.; Ma D. G.; Zhang D. D.; Duan L.Nat. Commun. 2023, 14, 2394.
[19] Tankeleviciute E.; Samuel I. D.W.; Zysman-Colman, E.J. Phys. Chem. Lett. 2024, 15, 1034.
[20] Lin Y. J.;Jimenez-Garcia, K.; Spielman, I. B.Nature. 2011, 471, 83.
[21] Li R.; Wu Z.-M.; Li X.-F.; Wang X.-F.; Song Y.-Z.; Fan J.-Z.; Zhang G.-P.; Wang C.-K.; Lin L.-L.Chin. J. Chem. Phys. 2025, 38, 334.
[22] Park I. S.; Min H.; Yasuda T.Angew. Chem. Int. Ed. 2022, 61, e202205684.
[23] Li Q.; Wu Y. L.; Yang Q. Q.; Wang S. M.; Shao S. Y.; Wang L. X.ACS Appl. Mater. Interfaces. 2022, 14, 49995.
[24] Zhang Y. W.; Zhang D. D.; Wei J. B.; Liu Z. Y.; Lu Y.; Duan L.Angew. Chem. Int. Ed. 2019, 58, 16912.
[25] Hu Y. X.; Miao J. S.; Hua T.; Huang Z. Y.; Qi Y. Y.; Zou Y.; Qiu Y. T.; Xia H.; Liu H.; Cao X. S.; Yang C. L.Nat. Photonics. 2022, 16, 803.
[26] Hu Y. X.; Miao J. S.; Zhong C.; Zeng Y.; Gong S. L.; Cao X. S.; Zhou X.; Gu Y.; Yang C. L.Angew. Chem. Int. Ed. 2023, 62, e202302478.
[27] Xu Y. C.; Cheng Z.; Li Z. Q.; Liang B. Y.; Wang J. X.; Wei J. B.; Zhang Z. L.; Wang Y.Adv. Opt. Mater. 2020, 8, 1902142.
[28] Wang J. J.; Li N. Q.; Zhong C.; Miao J. S.; Huang Z. Y.; Yu M. X.; Hu Y. X.; Luo S.; Zou Y.; Li K.; Yang C. L.Adv. Mater. 2023, 35, 2208378.
[29] Zhang H.; Zhang B.; Zhang Y. W.; Xu Z.; Wu H. Z.; Yin P. A.; Wang Z. M.; Zhao Z. J.; Ma D. G.; Tang B. Z.Adv. Funct. Mater. 2020, 30, 2002323.
[30] Zhu T.-J.; Li L.-Y. Semiconductor Technology. 2007, 04, 358(in Chinese). (朱彤珺, 李来运, 半导体技术, 2007, 04, 358.)
[31] Ji X.-Q.; Li W.-Z.; Zhong Z.-Y.; Wang T.; Jiang Y.-D.Chinese Journal of Quantum Electronics. 2006, 23(3), 416(in Chinese). (季兴桥, 黎威志, 钟志有, 王涛, 蒋亚东, 量子电子学报, 2006, 23(3), 416.
[32] An R. Z.; Zhao F. M.; Shang C. J.; Zhou M.; Cui L. S.Angew. Chem. Int. Ed. 2025, 64, e202420489.
[33] Zhang Y. W.; Wei J. B.; Zhang D. D.; Yin C.; Li G. M.; Liu Z. Y.; Jia X. Q.; Qiao J.; Duan L.Angew. Chem. Int. Ed. 2022, 61, e202113206.
[34] Wang J.; Zhang F.-J.; Xu Z.; Wang Y.-S.Acta Phys. -Chim. Sin. 2012, 28, 949(in Chinese). (王健, 张福俊, 徐征, 王永生, 物理化学学报, 2012, 28, 949.)
[35] Wang Q.; Huang T.-Y.; Zhang D.-D.; Duan L.Chinese Journal of Luminescence 2023, 44, 77(in Chinese). (王琪, 黄天宇, 张东东, 段炼, 发光学报, 2023, 44, 77.)
[36] Chang C. H.; Lu Y. J.; Liu C. C.; Yeh Y. H.; Wu C. C.Journal of Display Technology. 2007, 3, 193.
[37] Yang X. L.; Zhou X. W.; Zhang Y. X.; Li, D. L; Li, C. S.; You C. F.; Chou T. C.; Su S. J.; Chou P. T.; Chi Y.Adv. Sci. 2022, 9, 2201150.
[38] Li W. J.; Lin T. Y.; Zhu F.; Yan D. H.J. Mater. Chem. C. 2025, 13, 16954.
Options
Outlines

/

〈 〉