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

doi:10.6023/cjoc201906019

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3460-3466.DOI: 10.6023/cjoc201906019 Previous Articles Next Articles

Special Issue: 有机超分子化学合辑

基于苊并[1,2-b]喹喔嗪为受体单元设计合成新型红光热活化延迟荧光分子

俞佳^a, 肖雅方^b, 陈嘉雄^a

a 苏州大学功能纳米与软物质研究院苏州大学纳米协同创新中心江苏省碳基功能重点实验室江苏苏州 215123;
b 香港城市大学化学系香港九龙塘

收稿日期:2019-06-17 修回日期:2019-07-22 发布日期:2019-08-30
通讯作者: 陈嘉雄 E-mail:chenjiaxiong@suda.edu.cn
基金资助:
中国博士后科学基金（No.2018M640517）资助项目.

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

Yu Jia^a, Xiao Yafang^b, Chen Jiaxiong^a

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

Received:2019-06-17 Revised:2019-07-22 Published:2019-08-30
Supported by:
Project supported by the China Postdoctoral Science Foundation (No. 2018M640517).

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Abstract

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.

Key words: thermally activated delayed fluorescent, acenaphtho[1,2-b]quinoxaline, phenoxazine, red emitter, organic light-emitting diode

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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.

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基于苊并[1,2-b]喹喔嗪为受体单元设计合成新型红光热活化延迟荧光分子

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

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