Production method for electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-10761441-B2
Application number	US-201916411173-A
Country	US
Kind code	B2
Filing date	May 14, 2019
Priority date	May 15, 2018
Publication date	Sep 1, 2020
Grant date	Sep 1, 2020

Abstract

A method for producing an electrophotographic photosensitive member includes an electrically conductive substrate and a photosensitive layer. The method includes applying an application liquid for photosensitive layer formation containing a solvent, a binder resin, and a hole transport material directly or indirectly onto the electrically conductive substrate, and removing a portion of the solvent, to form the photosensitive layer. The solvent contains a first solvent that is an alcohol having a carbon number of at least 1 and no greater than 3, and a second solvent other than the first solvent. The binder resin includes a polyarylate resin that is a polymerization product of monomers including a first monomer represented by general formula (1) and a second monomer represented by general formula (2),

First claim

What is claimed is:

1. A method for producing an electrophotographic photosensitive member including an electrically conductive substrate and a photosensitive layer, the method comprising:
applying an application liquid for photosensitive layer formation containing a solvent, a binder resin, and a hole transport material directly or indirectly onto the electrically conductive substrate, and removing a portion of the solvent, to form the photosensitive layer,
wherein the solvent contains a first solvent that is an alcohol having a carbon number of at least 1 and no greater than 3, and a second solvent other than the first solvent, and
the binder resin includes a polyarylate resin that is a polymerization product of monomers including a first monomer and a second monomer, the first monomer including either of a compound represented by general formula (1-1) and a compound represented by general formula (1-2), the second monomer including at least one of a compound represented by chemical formula (2-1-1) and a compound represented by chemical formula (2-1-2),

where in the general formula (1-1),
R 11 and R 12 each represent, independently of one another, a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4,

2. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein
the second solvent contains at least one of methylene chloride, chloroform, tetrahydrofuran, and 1,3-dioxolane.

3. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein
the second monomer includes the compound represented by chemical formula (2-1-2).

4. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein
the binder resin includes at least one of polyarylate resins represented by chemical formulas (Resin-1), (Resin-2), (Resin-3), and (Resin 5),

5. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein
the content portion of the first solvent in the solvent is at least 0.5 mass % and no greater than 5.0 mass %.

6. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein
the first solvent contains at least one of methanol and 2-propanol.

7. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein
the hole transport material contains at least one of compounds represented by general formulas (10), (11), (12), and (13),

in the general formula (10),
R 101 , R 103 , R 104 , R 105 , R 106 , R 107 , and R 108 each independently represent a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 8, a phenyl group optionally substituted with an alkyl group having a carbon number of at least 1 and no greater than 8, or an alkoxy group having a carbon number of at least 1 and no greater than 8, two adjacent ones of R 103 , R 104 , R 105 , R 106 , and R 107 optionally taken together represent a cycloalkane having a carbon number of at least 5 and no greater than 7,
R 102 and R 109 each independently represent an alkyl group having a carbon number of at least 1 and no greater than 8, a phenyl group, or an alkoxy group having a carbon number of at least 1 and no greater than 8, and
b 1 and b 2 each independently represent an integer of at least 0 and no greater than 5,

in the general formula (11),
R 111 and R 112 each independently represent a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 8, or a phenyl group,
R 113 , R 114 , R 115 , R 116 , R 117 , and R 118 each independently represent an alkyl group having a carbon number of at least 1 and no greater than 8 or a phenyl group,
d 1 and d 2 each independently represent 0 or 1,
d 3 , d 4 , d 5 , and d 6 each independently represent an integer of at least 0 and no greater than 5, and
d 7 and d 8 each independently represent an integer of at least 0 and no greater than 4,

in the general formula (12),
R 121 , R 122 , R 123 , R 124 , R 125 , and R 126 each independently represent an alkyl group having a carbon number of at least 1 and no greater than 8, a phenyl group, or an alkoxy group having a carbon number of at least 1 and no greater than 8,
e 1 , e 2 , e 4 , and e 5 each independently represent an integer of at least 0 and no greater than 5, and
e 3 and e 6 each independently represent an integer of at least 0 and no greater than 4,

in the general formula (13), R 131 , R 132 , R 133 , R 134 , R 135 , R 136 , R 137 , R 138 , R 139 , and R 140 each independently represent a hydrogen atom or a methyl group.

8. The method for producing an electrophotographic photosensitive member according to claim 7 , wherein
in the general formula (10),
R 101 and R 108 represent a phenyl group substituted with an alkyl group having a carbon number of at least 1 and no greater than 8, or a hydrogen atom,
R 102 and R 109 represent an alkyl group having a carbon number of at least 1 and no greater than 8,
R 103 , R 104 , R 105 , R 106 , and R 107 each independently represent a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 8, or an alkoxy group having a carbon number of at least 1 and no greater than 8, and two adjacent ones of R 103 , R 104 , R 105 , R 106 , and R 107 are optionally taken together to form a cycloalkane having a carbon number of at least 5 and no greater than 7, and
b 1 and b 2 each independently represent 0 or 1,

in the general formula (11),
R 111 and R 112 each represent a hydrogen atom or a phenyl group,
R 113 , R 114 , R 115 , R 116 , R 117 , and R 118 each independently represent a methyl group or an ethyl group,
d 1 and d 2 each independently represent 0 or 1,
d 3 , d 4 , d 5 , and d 6 each independently represent an integer of at least 0 and no greater than 2, and
d 7 and d 8 each represent 0,

in the general formula (12),
R 121 , R 122 , R 123 , R 124 , R 125 , and R 126 each independently represent an alkyl group having a carbon number of at least 1 and no greater than 8,
e 1 , e 2 , e 4 , and e 5 each independently represent an integer of at least 0 and no greater than 2, and
e 3 and e 6 represent 0, and

in the general formula (13),
R 131 , R 132 , R 133 , R 134 , R 135 , R 136 , R 137 , R 138 , R 139 , and R 140 each represent a hydrogen atom.

9. The method for producing an electrophotographic photosensitive member according to claim 8 , wherein
the hole transport material contains at least one of compounds represented by chemical formulas (10-HT1), (10-HT2), (10-HT3), (10-HT4), (11-HT5), (11-HT6), (11-HT7), (12-HT8), (12-HT9), and (13-HT10),

Assignees

• Kyocera Document Solutions Inc

Inventors

• Azuma Jun
• Shimizu Tomofumi
• Kitaguchi Kenji
• Oji Kiichiro

Classifications

• G03G5/061473

  plural alkenyl groups linked directly to the same aryl group · CPC title

• G03G5/06147

  alkenylarylamine · CPC title

• G03G5/061446

  terphenyl-diamine · CPC title

• G03G5/061443

  benzidine · CPC title

• G03G5/056 Primary

  Polyesters · CPC title