Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3876-3887.DOI: 10.6023/cjoc202303022 Previous Articles     Next Articles


张越华a,c,d, 聂飞c,d, 周路c,d, 王晓烽c,d, 刘源c,d,*(), 霍延平c,e, 陈文铖c,d,*(), 赵祖金b,*()   

  1. a 广州城市职业学院 广州 510405
    b 华南理工大学发光材料与器件国家重点实验室 广州 510640
    c 广东工业大学轻工化工学院 广州 510006
    d 化学与精细化工广东省实验室揭阳分中心 广东揭阳 515200
    e 广东工业大学分析测试中心 广州 510006
  • 收稿日期:2023-03-15 修回日期:2023-05-30 发布日期:2023-07-12
  • 基金资助:
    国家自然科学基金(U2001222); 国家自然科学基金(U22A20399); 国家自然科学基金(52003058); 国家自然科学基金(21975055); 广东省基础与应用基础研究基金(2019B1515120035); 广东省基础与应用基础研究基金(2021A1515010607)

Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones

Yuehua Zhanga,c,d, Fei Niec,d, Lu Zhouc,d, Xiaofeng Wangc,d, Yuan Liuc,d(), Yanping Huoc,e, Wencheng Chenc,d(), Zujin Zhaob()   

  1. a Guangzhou City Polytechnic, Guangzhou 510405
    b State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640
    c School of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006
    d Jieyang Branch of Chemistry and Chemical Engineering Guangdong Laboratory, Jieyang, Guangdong 515200
    e Analysis and Test Center, Guangdong University of Technology, Guangzhou 510006
  • Received:2023-03-15 Revised:2023-05-30 Published:2023-07-12
  • Contact: E-mail:;;
  • Supported by:
    National Natural Science Foundation of China(U2001222); National Natural Science Foundation of China(U22A20399); National Natural Science Foundation of China(52003058); National Natural Science Foundation of China(21975055); Guangdong Basic and Applied Basic Research Foundation(2019B1515120035); Guangdong Basic and Applied Basic Research Foundation(2021A1515010607)

Two thermally activated delayed fluorescence (TADF) red-emitting materials 3 and 4 with aggregation-induced emission (AIE) properties were designed and synthesized using benzothiazole-2-yl(phenyl)methanone as acceptors, and phenoxazine and phenothiazine with strong electron-donating ability as donors to construct donor-acceptor (D-A) type molecules, and their thermal stability, electrochemical properties, single crystal structure, photophysical properties and electroluminescence properties were systematically studied. The two compounds have small singlet-triplet slitting (ΔEST, 0.04 and 0.16 eV) and microsecond-scale delayed lifetimes (0.63 and 1.30 μs), showing obvious TADF characteristics. Comparing the emission spectra before and after grinding in the powder state, it is found that compound 4 has obvious mechanochromic luminescence phenomenon. In neat-film state, the emission peaks of the two compounds were 683 and 654 nm, and photoluminescence quantum yields (PLQYs) were 0.8% and 3.6%, respectively. The non-doped organic light-emitting diode (OLED) devices based on compounds 3 and 4 obtained pure red emission (662 and 652 nm), and the maximum external quantum efficiencies (EQEs) of the devices were 0.15% and 0.34%, respectively. Although the luminous efficiencies of devices based on these two compounds are not high, their synthesis process is facile, which can provide useful insight for the development of red TADF materials based on benzothiazolyl ketones.

Key words: aggregation-induced emission (AIE) property, thermally activated delayed fluorescence (TADF) red light material, mechanochromic luminescence, benzothiazolyl ketones