具有D-π-A结构的咔唑衍生物的制备及其性能  

Synthesis and Properties of Carbazole Derivatives with D-π-A Structure

作　　者：张正垠[1,2] 赵鑫[1,2] 尹妮[1,2] 翟荣佳 林朝阳[1,2] 

机构地区：[1]苏州科技学院化学生物与材料工程学院,江苏苏州215009 [2]江苏省环境功能材料重点实验室,江苏苏州215009

出　　处：《化学世界》2014年第11期677-683,共7页Chemical World

摘　　要：以咔唑、5-醛基-2-噻吩硼酸、丙二腈为主要原料,通过Suzuki偶联、Knoevenagel缩合等反应,设计合成了三种具有D-π-A结构的咔唑类衍生物4a、4b、和4c,通过红外和核磁氢谱、核磁碳谱对它们的结构进行了表征,并考察了其紫外吸收光谱、荧光光谱、电化学行为和热稳定性。研究结果表明,4a、4b、和4c在二氯甲烷溶液中的紫外最大吸收波长均为471nm,在二氯甲烷溶液中具有良好的溶解性和溶液成膜性,它们的固态薄膜均在650nm附近辐射出很强的红色荧光,其荧光量子产率分别为66.42%、73.78%和76.18%;它们的最高占有分子轨道(HOMO)能级分别为-5.6eV、-5.8eV和-5.7eV,与正电极(ITO)的功函数(-4.8eV)相匹配,可有效降低空穴注入的能垒,有利于空穴的注入和传输;4a、4b和4c的热分解温度分别为354℃、350℃和203℃,其中4a、4b热稳定性较为突出,4c略差;因此4a、4b和4c有望作为一类具有空穴传输性能、可溶液加工性能的红光材料应用于发光器件中。With carbazole,5-formyl-2-thiophene boronic acid and malononitrile as raw materials,three carbazole derivatives with D-π-A structure were designed and synthesized by Suzuki coupling and Knoevenagel condensation.The structures of 4a、4band 4cwere characterized by IR、1 H NMR and 13 C NMR.Their UV-Vis spectra,fluorescence spectra,electrochemical behavior and thermal stability were studied respectively.The results showed that 4a、4band 4chad good solubility and solution film-forming property,and their maximum UV absorption in dichloromethane solution was at 471 nm.Both dichloromethane solution and solid state thin film of 4a、4band 4cemited strong red fluorescence,and their fluorescence quantum yields（φF）were 66.42%、73.78% and 76.18%.Their HOMO energy levels were-5.6eV、-5.8eV and-5.7eV which matched with the work function（-4.8eV）of the positive electrode（ITO）,so the barrier of hole-transport was effectively reduced.The results of TG curves showed that their thermal decomposition temperatures（Td）were 354℃、350℃ and 203℃,respectively,i.e.the thermal stability of 4aand 4bwas prominant,but that of 4cwas slihlly worse.Therefore,4a、4band 4ccould hopefully be applied to OLED for their good hole transport properties and solution processing ability as a series of potential red electroluminescent material.

关 键 词：合成 咔唑 D-π-A结构 性能 

分 类 号：TQ426.91[化学工程]