Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 761-770.DOI: 10.6023/cjoc201806017 Previous Articles     Next Articles



何煦, 肖燏萍, 袁鑫磊, 叶尚辉, 姜鸿基   

  1. 南京邮电大学信息材料与纳米技术研究院 有机电子与信息显示国家重点实验室培育基地 江苏省生物传感材料与技术重点实验室 江苏省有机电子与信息显示协同创新中心 南京 210023
  • 收稿日期:2018-06-13 修回日期:2018-09-21 发布日期:2018-11-12
  • 通讯作者: 姜鸿基
  • 基金资助:


Synthesis and Applications of Excimer Host Materials Based on 2,4,6-Triphenyl-1,3,5-triazine and Fluorene Moieties

He Xu, Xiao Yuping, Yuan Xinlei, Ye Shanghui, Jiang Hongji   

  1. Nanjing University of Posts and Telecommunications, Institute of Advanced Materials, Key Laboratory for Organic Electronics and Information Displays and Jiangsu Key Laboratory for Biosensors, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing 210023
  • Received:2018-06-13 Revised:2018-09-21 Published:2018-11-12
  • Contact: 10.6023/cjoc201806017
  • Supported by:

    Project supported by the Major Research Program from the State Ministry of Science and Technology (No. 2012CB933301), the National Natural Science Foundation of China (No. 21574068), the Priority Academic Program Development of Jiangsu Higher Education Institutions (No. YX03001) and the Natural Science Foundation of Jiangsu Province (No. BM2012010).

Three new bipolar derivatives based on 2,4,6-triphenyl-1,3,5-triazine and fluorene moieties, namely FTRZ, pTFTRZ and mTFTRZ were designed and synthesized by using 9-(4-(hexyloxy) phenyl) -9H-fluorene, 2-bromo-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris(4-bromophenyl) -1,3,5-triazine, and 2,4,6-tris(3-bromophenyl) -1,3,5-triazine through palladium-cata-lyzed cross-coupling reaction, which were reported as hosts for thermally activated delayed fluorescence organic light-emitting diodes (OLEDs). The 1H NMR, 13C NMR and MALDI-TOF-MS spectra were used to characterize the chemical structure of compounds FTRZ, pTFTRZ and mTFTRZ. Their thermal, photophysical and electrochemical properties as well as electroluminescent device performance were thoroughly investigated to correlate the optoelectronic properties with the topology-varied molecular structure. The thermal decomposition temperatures of compounds FTRZ, pTFTRZ and mTFTRZ are 427, 446 and 424℃ and their glass transition temperatures of compounds pFTRZ and mTFTRZ are 120 and 103℃, respectively. The optical band gaps of compounds FTRZ, pTFTRZ and mTFTRZ in toluene solution are 3.24, 3.29 and 3.24 eV, and their triplet energy levels are 3.04, 3.11 and 3.05 eV, respectively. Due to the π-π interaction between 2,4,6-triphenyl-1,3,5-triazine planes, compounds FTRZ, pTFTRZ and mTFTRZ form excimer in the thin film state. The electroluminescent properties of OLEDs using compounds FTRZ, pTFTRZ and mTFTRZ as the hosts and 2,4,5,6-tetrakis(carbazol-9-yl) -1,3-dicyanobenzene as the guest emitter were investigated. The green OLED of compound FTRZ as host material shows a peak emission at 510 nm with a maximum current efficiency of 6.7 cd/A, a maximum external quantum efficiency of 2.07% and a maximum brightness of 35718 cd/m2. The efficiency roll-offs of the OLEDs hosted by compounds FTRZ and pTFTRZ at 20000 cd/m2 are 3% and 2%, which are much better than the same device hosted by compound mTFTRZ.

Key words: organic light-emitting diode, 2,4,6-triphenyl-1,3,5-triazine, fluorene, host material, excimer