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-Diphenyl ethenyl) -N,N-bis[(4-methyl) -phenyl]aniline

作　　者：韩丽颖[1] 李祥高[1] 王世荣[1] 肖殷[1] 

机构地区：[1]天津大学化工学院精细化工系,天津300072

出　　处：《精细化工》2013年第10期1096-1101,共6页Fine Chemicals

基　　金：国家863计划(2012AA030307);国家自然科学基金(21176180);山西省自然科学基金(2011011022-5)~~

摘　　要：该文以二苯基溴甲烷和4-[N,N-二(4-甲苯基)]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-甲苯基)]氨基苯甲醛)∶n(叔丁醇钾)=5∶1∶0.7∶1.2,反应温度15℃,反应时间4 h,在该条件下收率为97.94%。在优化工艺条件下进行了10倍放大合成,产物平均收率96.79%。采用1HNMR、MS及FTIR对化合物结构进行了表征,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(R d)为10 V/s,光敏性(E1/2)为0.6 lux·s,残余电位(V R)为10 V,表现出优良的光导性能。4-（ 2, 2-Diphenylethenyl ） -N, N-bis [ （ 4-methyl ） phenyl ] aniline was synthesized from bromodiphenylmethane and 4-（ N, N-bis-4-methylphenyl ） aminobenzaldehyde via Wittig-Horner reaction. The relationship between the 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 was conducted under the above conditions and an average yield of 96.79% was obtained. The compound was characterized by means of 1HNMR, 13 CNMR, FTIR and MS. The highest occupied molecular orbital（HOMO） level and the lowest unoccupied molecular orbital（LUMO） of the compound were investigated by the cyclic vohammetry experiment, respectively. The organic photoconductive devices based on the titled compound as hole-transporting materials showed excellent xerographic performance,with V0 =550 V,VR = 10 V,Rd = 10 V/s,EI/2 =0. 6 lux · s.

关 键 词：空穴传输材料 Wittig—Horner反应 光电性能 功能材料 

分 类 号：TQ246.3[化学工程—有机化工]