METHODS FOR PRODUCING ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER AND ORGANIC DEVICE EACH HAVING CHARGE TRANSPORTING LAYER

• US 20140322434A1
• Filed: 12/06/2012
• Published: 10/30/2014
• Est. Priority Date: 12/22/2011
• Status: Active Grant

• Current Assignee: Canon Ayutthaya Limited (Canon Inc.)
• Original Assignee: Canon Ayutthaya Limited (Canon Inc.)
• Inventors: Yamagishi, Keiko, Okuda, Atsushi, Yoshimura, Kimihiro, Ogaki, Harunobu, Miyauchi, Yohei, Uematsu, Hiroki
• Granted Patent: US 9,282,615 B2
• Time in Patent Office: Days
• US Class Current: 427/74
• CPC Class Codes: G03G 5/047 characterised by the charge-generation layers or charge transport layers G03G5/0433 and G03G5/0436 take precedence
• CPC Class Codes: G03G 5/0503 Inert supplements
• CPC Class Codes: G03G 5/0514 not comprising cyclic groups
• CPC Class Codes: G03G 5/0525 Coating methods
• CPC Class Codes: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources

Abstract

A method for producing an electrophotographic photosensitive member has a charge transporting layer, including preparing a first solution containing a specified first liquid, a charge transporting substance and a binder resin, preparing a second solution containing a specified second liquid and water, preparing an emulsion from the first and second solutions, forming the emulsion coating, and heating the coat to form the charge transporting layer, and a method for producing an organic device has a charge transporting layer, including preparing a first solution containing a specified first liquid and a charge transporting substance, preparing a second solution containing a specified second liquid and water, preparing an emulsion from the first and second solutions, forming the emulsion coating, and heating the coat to form the charge transporting layer are used.

Claims

1. A method of producing an electrophotographic photosensitive member which comprises a support and a charge transporting layer formed thereon, comprising the steps of:

preparing a first solution comprising;

a first liquid having a solubility in water at 25°

C. and 1 atm of 1.0 mass % or less,

a charge transporting substance, and

a binder resin,

preparing a second solution comprising;

a second liquid having a solubility in water at 25°

C. and 1 atm of 5.0 mass % or more and a solubility in the first liquid at 25°

C. and 1 atm of 5.0 mass % or more, and

water,

dispersing the first solution in the second solution to prepare an emulsion,

forming a coat of the emulsion, and

heating the coat to form the charge transporting layer.

2. A method of producing an electrophotographic photosensitive member according to claim 1,

wherein the binder resin is a binder resin soluble in the first liquid.

3. A method of producing an electrophotographic photosensitive member according to claim 1,

wherein the second liquid is a liquid having a solubility in water at 25°

C. and 1 atm of 20.0 mass % or more.

4. A method of producing an electrophotographic photosensitive member according to claim 1,

wherein the ratio (w/(a+c)) is 5/5 to 7/3,

wherein w represents the mass of the water in the emulsion, a represents the mass of the first liquid in the emulsion, and c represents the mass of the second liquid in the emulsion.

5. A method of producing an electrophotographic photosensitive member according to claim 1,

wherein the ratio (a/c) is 97/3 to 30/70,

wherein a represents the mass of the first liquid in the emulsion, and c represents the mass of the second liquid in the emulsion.

6. A method of producing an electrophotographic photosensitive member according to claim 1,

wherein the first liquid is at least one selected from the group consisting of toluene, chloroform, dichlorobenzene, chlorobenzene, xylene, ethylbenzene, and phenetole.

7. A method of producing an electrophotographic photosensitive member according to claim 6,

wherein the first liquid is at least one selected from the group consisting of toluene and xylene.

8. A method of producing an electrophotographic photosensitive member according to claim 1,

wherein the second liquid is at least one selected from the group consisting of tetrahydrofuran, dimethoxymethane, 1,2-dioxane, 1,3-dioxane, 1,4-dioxane, 1,3,5-trioxane, methanol, 2-pentanone, ethanol, tetrahydropyran, diethylene glycol dimethyl ether, ethylene glycol dimethyl ether, propylene glycol n-butyl ether, propylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monoallyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether, propylene glycol diacetate, methyl acetate, ethyl acetate, n-propyl alcohol, 3-methoxybutanol, 3-methoxybutyl acetate, and ethylene glycol monomethyl ether acetate.

9. A method of producing an electrophotographic photosensitive member according to claim 8,

wherein the second liquid is at least one selected from the group consisting of tetrahydrofuran and dimethoxymethane.

10. A method of producing an organic device which comprises a charge transporting layer, comprising the steps of:

preparing a first solution comprising;

a first liquid having a solubility in water at 25°

C. and 1 atm of 1.0 mass % or less,

a charge transporting substance, and

a binder resin,

preparing a second solution comprising;

a second liquid having a solubility in water at 25°

C. and 1 atm of 5.0 mass % or more and a solubility in the first liquid at 25°

C. and 1 atm of 5.0 mass % or more, and

water,

dispersing the first solution in the second solution to prepare an emulsion,

forming a coat of the emulsion, and

heating the coat to form the charge transporting layer.

11. A method of producing an organic device according to claim 10,

wherein the first liquid is at least one selected from the group consisting of toluene, chloroform, dichlorobenzene, chlorobenzene, xylene, ethylbenzene, and phenetole.

12. A method of producing an organic device according to claim 10,

wherein the second liquid is at least one selected from the group consisting of tetrahydrofuran, dimethoxymethane, 1,2-dioxane, 1,3-dioxane, 1,4-dioxane, 1,3,5-trioxane, methanol, 2-pentanone, ethanol, tetrahydropyran, diethylene glycol dimethyl ether, ethylene glycol dimethyl ether, propylene glycol n-butyl ether, propylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monoallyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether, propylene glycol diacetate, methyl acetate, ethyl acetate, n-propyl alcohol, 3-methoxybutanol, 3-methoxybutyl acetate, and ethylene glycol monomethyl ether acetate.

13. A method of producing an electrophotographic photosensitive member which comprises a support and a charge transporting layer formed thereon, comprising the steps of:

preparing a first solution comprising;

a first liquid,

a charge transporting substance, and

a binder resin,

preparing a second solution comprising;

a second liquid, and

water,

dispersing the first solution in the second solution to prepare an emulsion,

forming a coat of the emulsion, and

heating the coat to form the charge transporting layer, and

wherein the first liquid is at least one selected from the group consisting of toluene, chloroform, dichlorobenzene, chlorobenzene, xylene, ethylbenzene, and phenetole, and

the second liquid is at least one selected from the group consisting of tetrahydrofuran, dimethoxymethane, 1,2-dioxane, 1,3-dioxane, 1,4-dioxane, 1,3,5-trioxane, methanol, 2-pentanone, ethanol, tetrahydropyran, diethylene glycol dimethyl ether, ethylene glycol dimethyl ether, propylene glycol n-butyl ether, propylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monoallyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether, propylene glycol diacetate, methyl acetate, ethyl acetate, n-propyl alcohol, 3-methoxybutanol, 3-methoxybutyl acetate, and ethylene glycol monomethyl ether acetate.