Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus, and chlorogallium phthalocyanine crystal and method for producing the same
An electrophotographic photosensitive member includes a support and a photosensitive layer in this order. The photosensitive layer contains a chlorogallium phthalocyanine crystal represented by formula (1) in which at least one organic compound selected from N,N-dimethylformamide and dimethyl sulfoxide is contained. The content of the organic compound contained in the chlorogallium phthalocyanine crystal represented by the formula (1) is 0.10 mass % or more and 0.80 mass % or less based on a content of the chlorogallium phthalocyanine crystal represented by the formula (1).
1. A method for producing a chlorogallium phthalocyanine crystal represented by formula (1) in which at least one organic compound selected from N,N-dimethylformamide and dimethyl sulfoxide is comprised, the method comprising:
a synthesis step of synthesizing a chlorogallium phthalocyanine crystal by reacting a gallium compound and a compound that forms a phthalocyanine ring in a chlorinating aromatic compound;
an acid pasting step of obtaining a hydroxygallium phthalocyanine crystal by performing an acid pasting treatment in which the chlorogallium phthalocyanine crystal obtained in the synthesis step is mixed with sulfuric acid;
a hydrochloric acid treatment step of obtaining a chlorogallium phthalocyanine crystal by mixing the hydroxygallium phthalocyanine crystal obtained in the acid pasting step with an aqueous hydrochloric acid solution; and
a wet milling step of obtaining a chlorogallium phthalocyanine crystal by mixing the chlorogallium phthalocyanine crystal obtained in the hydrochloric acid treatment step with at least one organic compound selected from N,N-dimethylformamide and dimethyl sulfoxide and performing a wet milling treatment,
wherein a content of the organic compound comprised in the chlorogallium phthalocyanine crystal represented by the formula (1) is 0.10 mass % or more and 0.80 mass % or less based on a content of the chlorogallium phthalocyanine crystal represented by the formula (1),
where X 1 to X 4 each independently represent a hydrogen atom or a chlorine atom.
2. The method for producing a chlorogallium phthalocyanine crystal according to claim 1 , wherein the gallium compound is gallium trichloride.
3. The method for producing a chlorogallium phthalocyanine crystal according to claim 1 , wherein the compound that forms a phthalocyanine ring is orthophthalonitrile and the chlorinating aromatic compound is α-chloronaphthalene.
4. The method for producing a chlorogallium phthalocyanine crystal according to claim 1 ,
wherein a concentration of the aqueous hydrochloric acid solution used in the hydrochloric acid treatment step is 10 mass % or more, and
an amount of hydrochloric acid in the aqueous hydrochloric acid solution used is 10 mol or more based on 1 mol of the hydroxygallium phthalocyanine used.
5. A method for producing an electrophotographic photosensitive member comprising:
a support;
a charge generating layer; and
a charge transporting layer in this order,
the method comprising:
preparing an application liquid for the charge generating layer; and
forming a coating film of the application liquid for the charge generating layer, followed by drying the coating film, to thereby form the charge generating layer, and wherein
the application liquid containing a chlorogallium phthalocyanine crystal being produced by the method according to claim 1 .