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Suppressing triplet exciton quenching by regulating the triplet energy of crosslinkable hole transport materials for efficient solution-processed TADF OLEDs

通过调节交联空穴传输材料三线态能级实现溶液法 制备高效的热活化延迟荧光有机电致发光二极管

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Abstract

Crosslinkable hole transport materials (HTMs) with high triplet energies would have a balance of carrier injection into the emitting material layer, suppressing the triplet exciton quenching and resulting in high-performance solution-processed organic light-emitting diode (OLED) devices. Two novel crosslinkable HTMs with different central units, N2, N8-di-p-tolyl-N2,N8-bis(4-vinylphenyl)dibenzo[b,d]thiophene-2,8-diamine (V-p-DBT) and N2,N8-di-p-tolyl-N2,N8-bis(4-vinylphenyl)dibenzo[b,d]furan-2,8-diamine (V-p-DBF), were designed and synthesized. The use of dibenzothiophene and dibenzofuran units increases the torsion angle compared with the commonly used N, N′-di-p-tolyl-N, N′-bis(4-vinylphenyl)-[1,1′-biphenyl]-4,4′-diamine (V-p-TPD), leading to high triplet energies of 2.57 and 2.64 eV, respectively. The triplet energies of V-p-DBT and V-p-DBF effectively suppress triplet exciton quenching. Furthermore, the crosslinked HTM layer showed excellent solvent-resistant abilities and high thermal stability. An outstanding maximum current efficiency (CEmax) of 79.94 cd A−1 and maximum external quantum efficiency (EQEmax) of 24.35% were obtained by V-p-DBF-based green thermally activated delayed fluorescent (TADF) OLEDs. This work provides a new molecular design strategy for achieving efficient solution-processed TADF OLEDs.

摘要

具有高三线态能级的交联空穴传输材料能够平衡发光层载流子 的复合并有效抑制三线态激子的猝灭, 对制备高性能溶液法有机电致 发光二极管具有重要意义. 本文设计合成了两种具有不同母核的新型 交联空穴传输材料, V-p-DBT和V-p-DBF. 与已报道的交联空穴传输材 料V-p-TPD相比, 二苯并噻吩和二苯并呋喃母核的引入增加了分子的 扭转角, 使两种化合物具有更高的三线态能级, 分别为2.57和2.64 eV. 通过瞬态荧光光谱证明它们能够有效地抑制三线态激子的猝灭. 交联 的空穴传输层表现出优异的抗溶剂能力和溶液工艺所需的理化性质. 其中, 基于V-p-DBF的绿色热活化延迟荧光有机发光二极管获得了 79.94 cd A−1的最大电流效率和24.35%的最大外量子效率. 这项工作为 实现溶液法制备的有机电致发光二极管提供了一种新的分子设计 策略.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (52173180), the Key Research and Development Project of Tianjin (19ZXNCGX00020), and the S&T Program of Hebei Province (20311401D).

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Authors and Affiliations

  1. School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300350, China

    Yifei Yan  (燕逸飞), Fei Zhang  (张飞), Hongli Liu  (刘红丽), Xianggao Li  (李祥高) & Shirong Wang  (王世荣)

  2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072, China

    Yifei Yan  (燕逸飞), Fei Zhang  (张飞), Hongli Liu  (刘红丽), Xianggao Li  (李祥高) & Shirong Wang  (王世荣)

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  1. Yifei Yan  (燕逸飞)
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  2. Fei Zhang  (张飞)
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  3. Hongli Liu  (刘红丽)
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  4. Xianggao Li  (李祥高)
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Contributions

Yan Y, Li X, and Wang S contributed to the conception of the study; Yan Y performed the experiment; Liu H, Zhang F, and Wang S contributed to the data analyses and manuscript preparation; Yan Y performed the data analyses and wrote the manuscript with the help of Zhang F; Li X and Wang S provided financial support.

Corresponding author

Correspondence to Shirong Wang  (王世荣).

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Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary information

Experimental details and supporting data are available in the online version of the paper.

Yifei Yan obtained his bachelor of engineering degree from Central South University in 2019. He is a master’s candidate at Tianjin University under the supervision of Prof. Shirong Wang. His research interests focus on the synthesis and applications of functionalized crosslinkable hole transport materials for electroluminescence.

Shirong Wang received her BS degree in 1991 from Tianjin University, China. She received her PhD degree from the Department of Applied Chemistry, Tianjin University. She was engaged in postdoctoral research at the State Key Laboratory of Fine Chemicals, Dalian University of Technology. In 1998, she was appointed as a professor at the School of Chemical Engineering, Tianjin University. Her main research interests include perovskite solar cells, organic/quantum dots light-emitting diodes, and metal halide perovskite nanocrystals.

Supplementary Information

40843_2022_2121_MOESM1_ESM.pdf

Suppressing triplet exciton quenching by regulating the triplet energy of crosslinkable hole transport materials for efficient solution-processed TADF OLEDs

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Yan, Y., Zhang, F., Liu, H. et al. Suppressing triplet exciton quenching by regulating the triplet energy of crosslinkable hole transport materials for efficient solution-processed TADF OLEDs. Sci. China Mater. 66, 291–299 (2023). https://doi.org/10.1007/s40843-022-2121-0

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