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Synthesis of Styryl Substituted Triphenylamines and Their Key Intermediate

Author: HuoWenMin
Tutor: WangShiRong
School: Tianjin University
Course: Applied Chemistry
Keywords: styryl substituted triphenylamine modified Ullmann reaction hole transporting material
CLC: O625.6
Type: Master's thesis
Year: 2008
Downloads: 127
Quote: 0
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Abstract


Styryl substituted triphenylamine is a sort of excellent performance hole transport material. The existence of styryl conjugate radicle could promote glass transition temperature, electron delocalization and carrier transport property. In this paper, the key intermediate 4,4′-dimethyl triphenylamine was synthesized through modified Ullmann reaction. The catalyst system and areaction conditions were researched on exploringly. The compositive catalyst system were that xylene, 2,2’-dipyridine and potassium tert-butoxide as solvent, ligand and base respectively, the molar ratio of cuprous choride, 2,2’-dipyridine, 4-methyl diphenylamine and p-iodotoluene was 0.5:0.5:1:1.8. The mixture was heated to 140℃refluxing for 8h, with the yield and purity of target compound as 80.8 % and 99.14 %.N,N-bis（p-methylphenyl）-4-（2-phenylethenyl） benzenamine and N,N-bis（p-methyl phenyl）-4-（2,2-diphenylethenyl） benzenamine were synthesized via wittig-horner reaction using 4,4′-dimethyl triphenylamine as intermediate. The composition and structure of intermediate and end products were confirmed by UV-Vis, IR, MS. The yields of two compounds were 96.4 % and 19.4 %. Some elementary studies about chloromethylation on triphenylamine were discussed also.The UV-Vis absorption of produts were tested, and the effect of conjugate structure on the spectroscopic propertie was discussed also. Organic photoconductive devices were fabricated respectively using synthesized compounds 4,4′-dimethyl triphenylamine, N,N-bis（p-methyl phenyl）-4-（2-phenylethenyl） benzenamine and N,N-bis（p-methyl phenyl）-4-（2,2-diphenylethenyl） benzenamine as hole transporting materials and Y-TiOPc as charge generation material. The performances of OPC were tested with data as V0=650 V, VR=170 V, RD=10 V/s, E1/2=0.90 lx·s;V0=490 V, VR=60 V, RD=35 V/s, E1/2=1.0 lx·s; V0=720 V, VR=28 V, RD=18.8 V,E1/2=0.75 lx·s, respectively. It is proved that styryl substituted triphenylamine had excellent hole-transporting properties.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Aromatic compounds > Aromatic nitrogen compounds
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