Method for producing electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-9304414-B2
Application number	US-201414160445-A
Country	US
Kind code	B2
Filing date	Jan 21, 2014
Priority date	Jan 28, 2013
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

A method for producing an electrophotographic photosensitive member having a charge transporting layer, the charge transporting layer being a surface layer, the method including drying a coat of a charge-transporting-layer coating liquid to form the charge transporting layer, wherein the charge-transporting-layer coating liquid contains components (α), (β), (γ) and (δ), and when the solubility of the component (α) in 100 g of the component (γ) is defined as X(g) and the solubility of the component (α) in 100 g of the component (δ) is defined as Y(g), solubility X and solubility Y satisfy a relationship of X>Y.

First claim

What is claimed is:

1. A method for producing an electrophotographic photosensitive member comprising a support, a charge generating layer formed on the support, and a charge transporting layer formed on the charge generating layer, the method comprising:
dissolving (α) and (β) with solvents of (γ) and (δ) to prepare a charge-transporting-layer coating liquid;
the (α) being a charge transporting substance,
the (β) being at least one resin selected from the group consisting of
a polycarbonate resin having a structural unit represented by the following formula (1A), and
a polyester resin having a structural unit represented by the following formula (1B),

the (γ) being an aromatic hydrocarbon solvent which is at least one selected from the group consisting of toluene, xylene and mesitylene, and
the (δ) being a compound having a boiling point under 1 atmosphere higher than that of the (γ),
forming a coat for the charge transporting layer using the charge-transporting-layer coating liquid, and
drying the coat to form the charge transporting layer,
wherein
the charge transporting layer is a surface layer,
the charge-transporting-layer coating liquid is free of any polyester resins having a siloxane structure at the end thereof and any polycarbonate resins having a siloxane structure at the end thereof; and
the (α), the (γ) and the (δ) satisfy the following expression:
X ( g )> Y ( g )

wherein,
X(g) represents the solubility of the (α) in 100 g of the (γ) in an environment at 23° C. under 1 atmosphere, and
Y(g) represents the solubility of the (α) in 100 g of the (δ) in an environment at 23° C. under 1 atmosphere;

wherein,
R 1 to R 4 each independently represent a hydrogen atom, a methyl group or a phenyl group,
X 1 represents a single bond, an oxygen atom, a cyclohexylidene group or a bivalent group represented by the following formula (A),
R 11 to R 14 each independently represent a hydrogen atom, a methyl group or a phenyl group,
X 2 represents a single bond, an oxygen atom, a cyclohexylidene group or a bivalent group represented by the following formula (A), and
Y 1 represents a meta-phenylene group, a para-phenylene group, a cyclohexylene group or a bivalent group represented by the following formula (B):

wherein,
R 21 and R 22 each independently represent a hydrogen atom, a methyl group, an ethyl group or a phenyl group,
R 31 to R 38 each independently represent a hydrogen atom, a methyl group or a phenyl group, and
X 3 represents a single bond, an oxygen atom, a sulfur atom or a methylene group, and
wherein the content of the (γ) is higher than the content of the (δ) in the charge-transporting-layer coating liquid.

2. The method for producing an electrophotographic photosensitive member according to claim 1 ,
wherein the (δ) is at least one compound selected from the group consisting of hexanol, heptanol, cyclohexanol, benzyl alcohol, ethylene glycol, 1,4-butanediol, 1,5-pentanediol, diethylene glycol, diethylene glycol ethyl methyl ether, ethylene carbonate, propylene carbonate, nitrobenzene, N-methylpyrrolidone, methyl benzoate, ethyl benzoate, benzyl acetate, ethyl-3-ethoxypropionate, acetophenone, methyl salicylate, dimethyl phthalate and sulfolane.

3. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein the charge-transporting-layer coating liquid further comprises
(ε) a compound having a boiling point under 1 atmosphere of 35 to 70° C.

4. The method for producing an electrophotographic photosensitive member according to claim 3 , wherein the (ε) is at least one compound selected from the group consisting of acetone, diethyl ether, methyl acetate, tetrahydrofuran and dimethoxymethane.

5. The method for producing an electrophotographic photosensitive member according to claim 3 , wherein the total content of the (γ) and (δ) based on the total content of the (γ), (δ) and (ε) in the charge-transporting-layer coating liquid is 50% by mass or more and 90% by mass or less.

6. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein the (α) is at least one selected from the group consisting of a triarylamine compound, a hydrazone compound, a styryl compound, a stilbene compound, a pyrazoline compound, an oxazole compound, a thiazole compound, a triarylmethane compound and an enamine compound.

7. The method for producing an electrophotographic photosensitive member according to claim 6 , wherein the (α) is at least one selected from the group consisting of a compound represented by the following formula (2), a compound represented by the following formula (3) and a compound represented by the following formula (4):

wherein, Ar 21 and Ar 22 each independently represent a phenyl group or a phenyl group substituted with a methyl group,
Ar 23 to Ar 28 each independently represent a phenyl group or a phenyl group substituted with a methyl group,
Ar 31 , Ar 32 , Ar 35 and Ar 36 each independently represent a phenyl group or a phenyl group substituted with a methyl group, and
Ar 33 and Ar 34 each independently represent a phenylene group or a phenylene group substituted with a methyl group.

8. The method for producing an electrophotographic photosensitive member according to claim 1 , wherein the drying temperature for drying the coat is 100° C. or higher and 140° C. or lower.

Assignees

• Canon Kk

Inventors

• Miura Daisuke
• Tanaka Daisuke
• Sugiyama Kazumichi

Classifications

• G03G5/0514

  not comprising cyclic groups · CPC title

• G03G5/056

  Polyesters · CPC title

• G03G5/0525

  Coating methods · CPC title

• G03G5/047 Primary

  characterised by the charge-generation layers or charge transport layers {(G03G5/0433 and G03G5/0436 take precedence)} · CPC title

• G03G5/0517

  comprising one or more cyclic groups consisting of carbon-atoms only · CPC title