4-（2,2-二苯基乙烯基）-N,N-二(4-甲苯基)苯胺的合成工艺优化及光电性能

Synthesis optimization and optoelectronic properties of 4-(2, 2–diphen -ylethenyl)-N, N-bis[(4-methyl) -phenyl] aniline

摘要:

本文以二苯基溴甲烷和4-[(N,N-二(4-甲基苯基）]氨基苯甲醛经Wittig-Horner反应合成了4-（2,2-二苯基乙烯基）-N,N-二(4-甲苯基)苯胺。考察了原料配比、反应温度及反应时间对收率的影响，得到优化的工艺条件为：n (亚磷酸三乙酯):n (二苯基溴甲烷):n (4-[(N,N-二(4-甲基苯基）]氨基苯甲醛):n (叔丁醇钾) = 5:1:0.7:1.2，反应温度为15℃，反应时间为4h，收率为97.94%。在此条件下进行了10倍放大合成，产物平均收率96.79%。采用1H-NMR，MS及FT-IR对结构进行了表征，根据C-V曲线法得到了化合物的HOMO和LUMO能级， 并以该化合物作为空穴传输材料制备激光有机光电导器件，充电电位( V0 ) 为550 V ，暗衰率( Rd )为10 V/s，半衰减曝光量( E1/2 )为0.6 lux.s，残余电位( VR )为10V，表现出优良的光导性能。

Abstract:

4-(2,2-diphenylethenyl)-N,N-bis[(4-methyl)phenyl] aniline was synthesized with bromodiphenylmethane and 4-(N,N-bis-4-methylphenyl) aminobenzaldehyde via Wittig-Horner reaction. The relationship between yield and reaction conditions, such as reaction time, temperature and the molar ratios of raw material was investigated and the yield could reach 97.94%. The 10 times amplification synthesis were conducted under the above conditions and got the average yield of 96.79%. The compound was characterized by 1H NMR, 13C NMR, FT-IR and MS. The highest occupied molecular orbital (HOMO) level and the lowest unoccupied molecular orbital (LUMO) of the compound were investigated by the cyclic voltammetry experiment, respectively. The organic photoconductive devices based on the titled compound as hole-transporting materials showed excellent xerographic performance, V0 = 550V，VR = 10 V，Rd = 10 V/s, E1/2 = 0.6 lux?s.