苯腙类光电材料的合成及其性能

Synthesis and Properties of Novel Phenylhydrazone Derivatives as Photoelectric Materials

以三苯胺、苯肼和芴酮为原料,通过甲酰化、亲核加成反应合成了4-(N,N-二苯基)氨基苯甲醛苯腙(PABPD)、4-(N,N-二苯基)氨基苯甲醛-3,5-二硝基苯腙(PABNPD)和芴酮苯腙(FPD)三种苯腙类有机光电材料。采用1 HNMR、FTIR和元素分析对该系列化合物的结构进行了表征,并考察了该类化合物的紫外-可见吸收光谱、荧光发射光谱、电化学性质及热稳定性质。实验结果表明:三种目标化合物的最大紫外吸收峰分别出现在374、422和395nm,且PABPD可在445nm附近发出较强的蓝色荧光,PABNPD可在543nm附近出现较强的绿色荧光,FPD可在465nm附近出现较弱的蓝色荧光;TG分析结果表明三种目标化合物具有较好的热稳定性;采用循环伏安法测得三种目标化合物的电离势分别为4.91、5.15和5.04eV,说明PABPD相对于PABNPD和FPD具有更为优良的空穴传输性能,因此PABPD是一种具有潜在应用前景的空穴传输材料和蓝光发光材料。

Three organic light-emitting materials of phenylhydrazone derivatives（4-（N,N-diphenyl）,aminobenzaldehydephenylhydrazone（PABPD）,4-（N,N-diphenyl）aminobenzaldehyde-3,5-dinitrophenylhydrazone（PABNPD） and fluorenonephenylhydrazone（FPD））,have been designed and synthesized on the basis of triphenylamine,phenylhydrazine and fluorenone by formylation reaction and nucleophilic addition reaction.The structures of the three target compounds were characterized by means of 1H nuclear magnetic resonance（NMR） spectroscopy,Fourier transform infrared（FTIR） spectroscopy and elemental analyses.Their ultraviolet-visible（UV-Vis） spectra,photoluminescence spectra,cyclic voltammetry curves and thermogravimetric（TG） curves were studied,respectively.The results show that the maximum absorption peaks of the three compounds are 374,422 and 395nm,respectively.They can emit fluorescence under different ultraviolet and the maximum emissive wavelengths are 445,543 and 465nm,respectively.The results of TG curves show that they have good thermal stability.The ionization potential energy levels are 4.91,5.15 and 5.04 eV,respectively.These results show that PABPD has better hole transport property than the others,and it might be applied as a hole-transporting material and organic electroluminescent material.