氟代四苯基联苯二胺衍生物的合成及其光谱和电化学性质  

Synthesis,Spectral and Electrochemical Properties of Fluorinated Tetraphenylbenzidine Derivatives

作　　者：徐清[1] 熊威[1] 王清琪[1] 刘新才[1] 潘晶[1] 干宁[1] 侯琳熙[1] 

机构地区：[1]宁波大学材料科学与化学工程学院新型功能材料及其制备科学国家重点实验室培育基地,浙江宁波315211

出　　处：《高校化学工程学报》2011年第6期1057-1061,共5页Journal of Chemical Engineering of Chinese Universities

基　　金：国家自然科学基金资助项目(20774083;20805024);浙江省自然科学基金资助项目(Y407288);浙江省教育厅科研基金资助项目(20070968);宁波市自然科学基金资助项目(2010A610146);宁波市应用型专业人才培养基地建设项目(Jd090104);宁波大学王宽诚幸福基金资助项目

摘　　要：通过钯催化的Buchwald-Hartwig反应合成了三种新型的氟代四苯基联苯二胺衍生物N,N'-二苯基-N,N'-二(2,4-二氟苯基)-[1,1'-联苯]-4,4'-二胺(TFTPB1),N,N'-二苯基-N,N'-二(3,4-二氟苯基)-[1,1'-联苯]-4,4'-二胺(TFTPB2)和N,N'-二苯基-N,N'-二(3,5-二氟苯基)-[1,1'-联苯]-4,4'-二胺(TFTPB3),产率分别为42%,73%和76%。利用元素分析、熔点测试、FT-IR光谱和1H-NMR谱等手段确定了其分子结构,并利用紫外-可见吸收光谱、荧光光谱和电化学循环伏安法(CV)对其光谱和电化学性质进行了研究。结果表明,TFTPB1,TFTPB2和TFTPB3薄膜的最大吸收峰波长分别为337,347和346 nm,其荧光发射峰波长分别为405,417和406 nm,最高占有轨道(HOMO)能级分别为–5.41,–5.47和–5.59 eV,有望成为优良的空穴传输材料,也有望通过设计合理的器件结构实现电致蓝光发射。Three novel fluorinated tetraphenylbenzidine derivatives,N,N＇-diphenyl-N,N＇-bis（2,4-difluorophenyl）-[1,1＇-biphenyl]-4,4＇-diamine（TFTPB1）,N,N＇-diphenyl-N,N＇-bis（3,4-difluorophenyl）-[1,1＇-biphenyl]-4,4＇-diamine（TFTPB2） and N,N＇-diphenyl-N,N＇-bis（3,5-difluorophenyl）-[1,1＇-biphenyl]-4,4＇-diamine（TFTPB3）,were synthesized via palladium-catalyzed Buchwald-Hartwig reaction with the yields of 42%,73% and 76%,respectively.Their molecular structures were characterized by elemental analysis,melting points,FT-IR and 1H-NMR spectrum.Their spectral and electrochemical properties were investigated by UV-Vis absorption,fluorescence spectrum and electrochemical cyclic voltammetry（CV）.The results show that,TFTPB1,TFTPB2 and TFTPB3 films have maximum absorption at 337,347 and 346 nm respectively,and they can emit intense blue fluorescence with peak wavelengths at 405,417 and 406 nm,respectively,under ultraviolet excitation at 350 nm.The highest occupied molecular orbital（HOMO） energy levels determined from CV for TFTPB1,TFTPB2 and TFTPB3 are –5.41,–5.47 and –5.59 eV,respectively.These results suggest that the three compounds can be promising candidates for hole transport materials and blue electroluminescent materials.

关 键 词：四苯基联苯二胺 氟代作用 合成 空穴传输材料 

分 类 号：O649.5[理学—物理化学] O657[理学—化学]