Study On The Synthesis And Photo-conductivities Of Bisazo Compounds With Benzoxazole Moiety

Due to their high sensitivity, low dark decay, excellent photoelectrical stability, wide spectral range and low cost, the azo compounds are a kind of good charge-generation materials, widely used in organic photoconductors(OPC). In this thesis, the preparation of couplers with naphthoylurea moiety was investigated in detail, followed by the synthesis and the photoconductive properties of the bisazo compounds. Firstly, 3-hydroxy-2-naphthoylchloride was prepared by 3-hydroxy-2- naphthoic acid and SOCl2, with the optimal process conditions studied. Secondly, the optimal process conditions of 2-chlorophenylurea synthesized by 2-chloroaniline and NaNCO were studied, and five substituted phenylureas were synthesized by the same route. Thirdly, N-(2-chlorophenyl)-N′-(3-hydroxy-2-naphthoyl)urea and N-(3- methylphenyl)-N′-(3-hydroxy-2-naphthoyl)urea were obtained by 3-hydroxy-2- naphthoylchloride and 2-chlorophenylurea or 3-methylphenylurea, respectively. And their optimal process conditions were studied, respectively. Then four N-substituted- N′-(3-hydroxy-2-naphthoyl)ureas were synthesized by the same route. Finally, six bisazo compounds, with 2-(4'-amido-phenyl)-6-amidobenzoxazole as the diazo component and naphthoylureas as the coupling component, were synthesized by coupling reaction. Also the photoconductivity of the synthesized bisazo compounds was researched. The structures and purities of the synthesized compounds were confirmed by MS, IR, UV, EA, 13C NMR, XRD and HPLC.At last, the photo-conductivities of the bisazo compounds were studied. X-ray diffraction and UV showed that the post-treatment of the final products had influedce on the crystal structures and the absorptions of the bisazo compounds. The better post-treatment was obtained and the final product obtained by this treatment had a good photoconductive performance. The bisazo compound with ortho-methyl group in coupling component had the better xerographic performance, V0=550V,VR=40V,E1/2=2.4lx.s. When the OPC of functional separation type were fabricated, the experiments suggested that the less quantity of the resin and the more quantity of the solvent, the better xerographic performance of the OPC.