Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus, and chlorogallium phthalocyanine crystal and method for producing the same

Patent metadata

Field	Value
Publication number	US-9746790-B2
Application number	US-201514920631-A
Country	US
Kind code	B2
Filing date	Oct 22, 2015
Priority date	Oct 29, 2014
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

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).

First claim

What is claimed is:

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 .

Assignees

• Canon Kk

Inventors

• Nishida Tsutomu
• Tanaka Masato
• Kawahara Masataka

Classifications

• G03G5/0696 Primary

  Phthalocyanines · CPC title