Phthalocyanine compounds, process for production thereof and electrophotographic photosensitive member using the compounds

摘要

Iodogallium phthalocyanine and bromogallium phthalocyanine having novel crystalline forms characterized by X-ray diffraction patterns according to CuKa characteristic X-ray diffraction method and exhibiting excellent zirconium phthalocyanine can be obtained through appropriate selection of a reaction solvent, followed by milling or stirring in an appropriate solvent. For example, ±-chloronaphthalene is a suitable solvent for reaction between phthalonitrile and gallium triiodide or tribromide to provide iodogallium phthalocyanine or bromogallium phthalocyanine. Reaction of chlorogallium phthalocyanine or hydroxygallium phthalocyanine with hydroiodic (or hydrobromic) acid is also effective for providing a novel crystal form of iodo- (or bromo-)gallium phthalocyanine. Zirconium phthalocyanine exhibiting good electrophotographic performances can be obtained through a similar process.