基于2,4,6-三苯基-1,3,5-三嗪和芴单元的激基缔合物主体材料的制备与应用

doi:10.6023/cjoc201806017

有机化学 ›› 2019, Vol. 39 ›› Issue (3): 761-770.DOI: 10.6023/cjoc201806017 上一篇下一篇

研究论文

基于2,4,6-三苯基-1,3,5-三嗪和芴单元的激基缔合物主体材料的制备与应用

何煦, 肖燏萍, 袁鑫磊, 叶尚辉, 姜鸿基

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 E-mail:iamhjjiang@njupt.edu.cn
基金资助:
江苏省江苏省自然科学基金（No.BM2012010）资助项目.

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

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 E-mail:iamhjjiang@njupt.edu.cn
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).

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1. 基于2,4,6-三苯基-1,3,5-三嗪和芴单元的激基缔合物主体材料的制备与应用.PDF(787KB)

摘要/Abstract

设计合成了三种基于2，4，6-三苯基-1，3，5-三嗪和芴单元的双极性主体材料FTRZ，pTFTRZ和mTFTRZ.分别研究了它们的热稳定性、光物理性能、电化学性质和电致发光器件性能与分子的拓扑结构之间的关系.FTRZ，pTFTRZ和mTFTRZ的热分解温度均在400℃以上，pTFTRZ和mTFTRZ的玻璃化转变温度分别是103和120℃.化合物FTRZ，pTFTRZ和mTFTRZ在甲苯溶液中的光学带隙分别为3.24，3.29和3.24 eV，它们的三重态能级分别为3.04，3.11和3.05 eV.由于2，4，6-三苯基-1，3，5-三嗪平面间的π-π作用，化合物FTRZ，pTFTRZ和mTFTRZ在薄膜状态下形成激基缔合物，荧光发射光谱明显红移.最后研究了FTRZ，pTFTRZ和mTFTRZ作为客体发光分子2，4，5，6-四（9-咔唑基）-间苯二腈的主体材料在绿色热活化延迟荧光电致发光器件中的应用.以化合物FTRZ作为主体材料的绿色有机电致发光器件（OLED）表现出更好的电致发光性能，最大电流效率为6.7 cd/A，最大外量子效率为2.07%，最大亮度为35718 cd/m²，远优于以pTFTRZ和mTFTRZ作为主体材料的绿光器件.

关键词: 有机发光二极管, 2,4,6-三苯基-1,3,5-三嗪, 芴, 主体材料, 激基缔合物

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

引用此文

何煦, 肖燏萍, 袁鑫磊, 叶尚辉, 姜鸿基. 基于2,4,6-三苯基-1,3,5-三嗪和芴单元的激基缔合物主体材料的制备与应用[J]. 有机化学, 2019, 39(3): 761-770.

He Xu, Xiao Yuping, Yuan Xinlei, Ye Shanghui, Jiang Hongji. Synthesis and Applications of Excimer Host Materials Based on 2,4,6-Triphenyl-1,3,5-triazine and Fluorene Moieties[J]. Chin. J. Org. Chem., 2019, 39(3): 761-770.

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基于2,4,6-三苯基-1,3,5-三嗪和芴单元的激基缔合物主体材料的制备与应用

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

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