Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

• US 6,818,368 B2
• Filed: 04/12/2001
• Issued: 11/16/2004
• Est. Priority Date: 04/14/2000
• Status: Expired due to Fees

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Tanaka, Takakazu, Nakajima, Yuka, Ohgaki, Harunobu, Kunieda, Mitsuhiro
• Primary Examiner(s): Dote, Janis L.
• Application Number:
  US09/832,920
• Publication Number:
  US 20020048710A1
• Time in Patent Office: 1,314 Days
• Field of Search: 430/56, 430/58.65, 430/58.75, 430/58.8, 430/72, 430/73, 430/135, 399/115, 399/116, 399/159, 399/176, 564/307, 564/308, 564/309
• US Class Current: 430/73
• CPC Class Codes: G03G 5/043 Photoconductive layers characterised by having two or more layers or characterised by their composite structure
• CPC Class Codes: G03G 5/0605 Carbocyclic compounds
• CPC Class Codes: G03G 5/06142 arylamine
• CPC Class Codes: G03G 5/061443 benzidine
• CPC Class Codes: G03G 5/06147 alkenylarylamine

Abstract

An electrophotographic photosensitive member includes a charge generating material and a charge transfer material. The charge transfer material contains a triarylamine compound synthesized from an amine compound and an aryl halide in the presence of a catalyst comprising a phosphine compound represented by formula (1) and a palladium compound:

wherein Ar¹ to Ar³ are each independently an alkyl or aryl group which may have a substituent group, and at least one of Ar¹ to Ar³ is an aryl group. A process cartridge includes the electrophotographic photosensitive member.

Claims

1. A process cartridge comprising:

an electrophotographic photosensitive member and contact charging means for charging the electrophotographic photosensitive member, the electrophotographic photosensitive member and the contact charging means being integrated, and being attachable to and detachable from an electrophotographic apparatus body,

the electrophotographic photosensitive member comprising a charge generating material and a charge transfer material, wherein the charge transfer material is a triphenylamine compound and is synthesized from an amine compound and an aryl halide in the presence of a catalyst comprising a phosphine compound represented by formula (1) and a palladium compound;

wherein Ar¹ to Ar³ are each independently an alkyl or aryl group which may have a substituent group, and at least one of Ar¹ to Ar³ is an aryl group which may have a substituent group, and at least one of Ar¹ to Ar³ is a tert-butyl group,

the triphenylamine compound is represented by formula (CT-8);

2. A process cartridge according to claim 1, wherein the triphenylamine compound is synthesized in the presence of a base.

3. A process cartridge according to claim 2, wherein the base is an alkali metal alkoxide.

4. A process cartridge according to claim 3, wherein the alkali metal alkoxide is a sodium tert-butoxide.

5. A process cartridge according to claim 1, wherein the phosphine compound has a biphenyl group which may have at least one substituent group.

6. A process cartridge according to claim 1, wherein the phosphine compound is di-tert-butylbiphenylphosphine.

7. An electrophotographic apparatus comprising:

an electrophotographic photosensitive member, contact charging means for charging the electrophotographic photosensitive member, exposure means for exposing the charged electrophotographic photosensitive member for forming an electrostatic latent image, developing means for developing the electrostatic latent image formed on the electrophotographic photosensitive member with a toner, and transfer means for transferring the toner image formed on the electrophotographic photosensitive member onto a transfer member,

the electrophotographic photosensitive member comprising a charge generating material and a charge transfer material, wherein the charge transfer material is a triphenylamine compound and is synthesized from an amine compound and an aryl halide in the presence of a catalyst comprising a phosphine compound represented by formula (1) and a palladium compound;

wherein Ar¹ to Ar³ are each independently an alkyl or aryl group which may have a substituent group, and at least one of Ar¹ to Ar³ is an aryl group which may have a substituent group, and at least one of Ar¹ to Ar³ is a tert-butyl group,

the triphenylamine compound is represented by formula (CT-8);

8. An electrophotographic apparatus according to claim 7, wherein the triphenylamine compound is synthesized in the presence of a base.

9. An electrophotographic apparatus according to claim 8, wherein the base is an alkali metal alkoxide.

10. An electrophotographic apparatus according to claim 9, wherein the alkali metal alkoxide is a sodium tert-butoxide.

11. An electrophotographic apparatus according to claim 7, wherein the phosphine compound has a biphenyl group which may have at least one substituent group.

12. An electrophotographic apparatus according to claim 7, wherein the phosphine compound is di-tert-butylphenylphosphine.

13. A process cartridge comprising:

an electrophotographic photosensitive member and contact charging means for charging the electrophotographic photosensitive member,

the electrophotographic photosensitive member and the contact charging means being integrated, and being attachable to and detachable from an electrophotographic apparatus body,

the electrophotographic photosensitive member comprising a charge generating material and a charge transfer material, wherein the charge transfer material is a triphenylamine compound and is synthesized from an amine compound and an aryl halide in the presence of a catalyst comprising a phosphine compound and a palladium compound,

the triphenylamine compound is represented by formula (CT-8);

wherein the phosphine compound is

and the palladium compound is tris (dibenzylidenacetone) dipalladium(0).

14. An electrophotographic apparatus comprising:

an electrophotographic photosensitive member, contact charging means for charging the electrophotographic photosensitive member, exposure means for exposing the charged electrophotographic photosensitive member for forming an electrostatic latent image, developing means for developing the electrostatic latent image formed on the electrophotographic photosensitive member with a toner, and transfer means for transferring the toner image formed on the electrophotographic photosensitive member onto a transfer member,

the electrophotographic photosensitive member comprising a charge generating material and a charge transfer material, wherein the charge transfer material is a triphenylamine compound and is synthesized from an amine compound and an aryl halide in the presence of a catalyst comprising a phosphine compound and a palladium compound,

the triphenylamine compound is represented by formula (CT-8);

wherein the phosphine compound is

and the palladium compound is tris (dibenzylidenacetone) dipalladium(0).