一种新型三苯胺类空穴传输材料的合成与性能研究  

Synthesis and Properties of a Novel Triphenylamine Hole Transport Material

作　　者：张松林 李巍[1,2,3] 冯文慧 汪天洋 刘东志 周雪琴[1,2,3] Zhang Songlin;Li Wei;Feng Wenhui;Wang Tianyang;Liu Dongzhi;Zhou Xueqin(School of Chemical Engineering and Technology,Tianjin University,Tianjin 300350,China;Collaborative Innovation Center of Chemical Science and Engineering,Tianjin 300072,China;Tianjin Engineering Research Center of Functional Fine Chemicals,Tianjin 300350,China)

机构地区：[1]天津大学化工学院,天津300350 [2]天津化学化工协同创新中心,天津300072 [3]天津市功能精细化学品技术工程中心,天津300350

出　　处：《化学工业与工程》2020年第3期23-30,共8页Chemical Industry and Engineering

基　　金：国家自然科学基金资助(21776207和21576195)。

摘　　要：以2,7-二碘-9,9-二甲基芴为原料分别经过Buchwald-Hartwig交叉偶联反应、Ullmann反应,对目标化合物9,9-二甲基N2,N7二苯基N2,N7二-对甲苯基-9H-芴-2,7-二胺(d-TPA)进行合成研究。通过1H NMR、13C NMR以及HRMS-ESI等表征方法确定结构的正确性。研究表明:以铜粉为催化剂的Ullmann反应收率为85%,是最高效的合成方法。通过X射线衍射(XRD)测试和循环伏安法(CV)测试,结果表明:该材料为非晶材料,成膜性较好,且目标化合物的HOMO轨道能级值为-5. 23 eV,与常用阳极材料ITO功函相近且化学稳定性较好,有利于空穴由阳极向空穴传输层的注入。将目标化合物用作空穴传输材料制备了有机发光二级管(OLED)并进行性能测试表征,结果显示:所得器件的启亮电压为3. 8 V,最大发光亮度为21 412 cd/m2,最大电流效率为4. 78 cd/A,表明该化合物有望成为一种性能优异的新型空穴传输材料。Using 2,7-diiodo-9,9-dimethylindole as starting material,the Buchwald-Hartwig cross-coupling reaction and Ullmann reaction were used to obtain the target compound 9,9-dimethyl-N2,N7-diphenylN2,N7-di-P-tolyl-9 H-fluorene-2,7-diamine( d-TPA). The elucidation of chemical structure was proved by 1H NMR,13C NMR and HRMS-ESI. It is shown that the Ullmann reaction with copper powder as the catalyst is the most efficient synthetic method( yield 85%). From the results of X-ray diffraction( XRD)and cyclic voltammetry( CV),the material was amorphous and has the ability to form a good thin film.And the compound has a highest occupied molecular orbit( HOMO) energy level of-5. 23 eV,which is similar to the common anode material ITO work function and has good chemical stability,which is beneficial for the injection of hole carriers to the counter electrode. Organic lighting-emitting diodes( OLED)using the compound as hole transport material was prepared and characterized. The results show that the device has a light-emitting voltage of 3. 8 V,a maximum luminance of 21 412 cd/m2 and a maximum current efficiency of 4. 78 cd/A. From the results,it has been proved that the compound is expected to be a novel hole transport material with excellent performance.

关 键 词：三苯胺 合成 ULLMANN反应 非晶材料 OLED 空穴传输材料 

分 类 号：O621[理学—有机化学]