Electrophotographic photosensitive member, and apparatus and process cartridge provided with the same

• US 5,876,888 A
• Filed: 07/02/1997
• Issued: 03/02/1999
• Est. Priority Date: 07/04/1996
• Status: Expired due to Term

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Yoshida, Akira, Anayama, Hideki
• Primary Examiner(s): GOODROW, JOHN L
• Application Number:
  US08/887,425
• Time in Patent Office: 608 Days
• Field of Search: 430/58, 430/59, 430/66, 430/96, 349/297, 349/149
• US Class Current: 430/58.2
• CPC Class Codes: G03G 5/14756 Polycarbonates
• CPC Class Codes: G03G 5/14773 Polycondensates comprising silicon atoms in the main chain

Abstract

A surface layer of a photosensitive layer contains at least one resin selected from the group consisting of (a) a polyarylate resin having a structural unit represented by the following general formula (1) and (b) a polycarbonate resin having a structural unit represented by the following general formula (2): ##STR1## wherein, X₁ and X₂ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁ to R₈ and R₁₁ to R₁₄ are each hydrogen, halogen, or substituted or unsubstituted alkyl or aryl and are the same or different, and R₉ and R₁₀ are each hydrogen, halogen, or substituted or unsubstituted silyl, alkyl or aryl and are the same or different, and n is an integer of 2 or more; ##STR2## wherein X₃ and X₄ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁₅ to R₂₂ are each hydrogen, halogen, substituted or unsubstituted alkyl or aryl and are the same or different, R₂₃ and R₂₄ are each hydrogen, halogen, substituted or unsubstituted silyl, alkyl or aryl and are the same or different, and m is an integer of 2 or more.

Claims

1. An electrophotographic photosensitive member comprising:

a substrate and a photosensitive layer formed thereon, a surface layer of the photosensitive layer containing at least one resin selected from the group consisting of (a) a polyarylate resin having a structural unit represented by the following general formula (1) and (b) a polycarbonate resin having a structural unit represented by the following general formula (2);

##STR16## wherein, X₁ and X₂ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁ to R₈ and R₁₁ to R₁₄ are each hydrogen, halogen, or substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and R₉ and R₁₀ are each hydrogen, halogen, or substituted or unsubstituted silyl, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and n is an integer of 2 or more;

##STR17## wherein X₃ and X₄ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁₅ to R₂₂ are each hydrogen, halogen, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, R₂₃ and R₂₄ are each hydrogen, halogen, substituted or unsubstituted silyl, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and m is an integer of 2 or more.

2. An electrophotographic photosensitive member according to claim 1, wherein said at least one resin is a polyarylate resin.

3. An electrophotographic photosensitive member according to claim 1, wherein X₁ and X₂ are each single bond, --O-- or unsubstituted ethylene, R₁ to R₈ are each hydrogen, R₉ is phenyl, R₁₀ is methyl, and n is 5 or 7.

4. An electrophotographic photosensitive member according to claim 2, wherein said polyarylate resin further comprises the following structural unit:

##STR18## wherein X₅ is single bond, --O--, --S--, or substituted or unsubstituted alkylidene or substituted or unsubstituted cycloalkylidene, and R₁₁ to R₁₄ and R₂₅ to R₃₂ are each hydrogen, halogen, or substituted or unsubstituted alkyl or substituted or unsubstituted aryl.

5. An electrophotographic photosensitive member according to claim 4, wherein, said structural unit comprises a combination selected from the group consisting of (i) X₅ being isopropylidene and each of R₂₅ to R₃₂ being hydrogen;

(ii) X₅ being cyclohexylidene and each of R₂₅ to R₃₂ being hydrogen; and

(iii) X₅ being isopropylidene, each of R₂₅ and R₃₂ being methyl and each of R₂₆ to R₃₁ being hydrogen.

6. An electrophotographic photosensitive member according to claim 2, wherein said polyarylate resin is synthesized from (i) a bisphenol represented by the following general formula (3) and (ii) an aromatic dicarboxylic acid:

##STR19## wherein X₁, X₂, R₁ to R₁₀ and n are the same as in the general formula (1).

7. An electrophotographic photosensitive member according to claim 6, wherein said aromatic dicarboxylic acid is represented by the following general formula (4):

##STR20## wherein R₁₁ to R₁₄ are the same as in the general formula (1).

8. An electrophotographic photosensitive member according to claim 1, wherein said at least one resin is a polycarbonate resin.

9. An electrophotographic photosensitive member according to claim 8, wherein X₃ and X₄ are each single bond, --O-- or unsubstituted ethylene, R₁₅ to R₂₂ ar each hydrogen, R₂₃ is phenyl, R₂₄ is methyl, and m is 5 or 7.

10. An electrophotographic photosensitive member according to claim 8, wherein said polycarbonate resin further comprises the following structural unit:

##STR21## wherein X₅ is single bond, --O--, --S--, or substituted or unsubstituted alkylidene or substituted or unsubstituted cycloalkylidene, and R₂₅ to R₃₂ are each hydrogen, halogen, or substituted or unsubstituted alkyl or substituted or unsubstituted aryl.

11. An electrophotographic photosensitive member according to claim 10, wherein said structural unit comprises a combination selected from the group consisting of (i) X₅ being isopropylidene and each of R₂₅ to R₃₂ being hydrogen;

(ii) X₅ being cyclohexylidene and each of R₂₅ to R₃₂ being hydrogen; and

(iii) X₅ being isopropylidene, each of R₂₅ and R₃₂ being methyl and each of R₂₆ to R₃₁ being hydrogen.

12. An electrophotographic photosensitive member according to claim 8, wherein said polycarbonate resin is synthesized from (i) a bisphenol represented by the following general formula (5) and (ii) phosgene:

##STR22## wherein X₃, X₄, R₁₅ to R₂₄, and m are the same as in the general formula (2).

13. An electrophotographic photosensitive member according to claim 1, wherein said photosensitive layer is a laminate in this order of a charge generating layer and a charge transfer layer on the substrate and the resin is present in the charge transfer layer as the surface layer.

14. A process cartridge, comprising:

an electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, a developing means and a cleaning means, said electrophotographic photosensitive member and said at least one means being integrally supported and detachable from an electrophotographic apparatus main body, said electrophotographic photosensitive member comprising;

a substrate and a photosensitive layer formed thereon, a surface layer of the photosensitive layer containing at least one resin selected from the group consisting of (a) a polyarylate resin having a structural unit represented by the following general formula (1) and (b) a polycarbonate resin having a structural unit represented by the following general formula (2);

##STR23## wherein, X₁ and X₂ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁ to R₈ and R₁₁ to R₁₄ are each hydrogen, halogen, or substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and R₉ and R₁₀ are each hydrogen, halogen, or substituted or unsubstituted silyl, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and n is an integer of 2 or more;

##STR24## wherein X₃ and X₄ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁₅ to R₂₂ are each hydrogen, halogen, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, R₂₃ and R₂₄ are each hydrogen, halogen, substituted or unsubstituted silyl, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and m is an integer of 2 or more.

15. A process cartridge according to claim 14, wherein said at least one resin is polyarylate resin.

16. A process cartridge according to claim 14, wherein said at least one resin is polycarbonate resin.

17. A process cartridge according to claim 14, wherein said charging means is a contact charging means.

18. An electrophotographic apparatus, comprising:

an electrophotographic photosensitive member, a charging means, an exposure means, a developing means and a cleaning means, said electrophotographic photosensitive member comprising a substrate and a photosensitive layer formed thereon, a surface layer of the photosensitive layer containing at least one resin selected from the group consisting of (a) a polyarylate resin having a structural unit represented by the following general formula (1) and (b) a polycarbonate resin having a structural unit represented by the following general formula (2);

##STR25## wherein, X₁ and X₂ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁ to R₈ and R₁₁ to R₁₄ are each hydrogen, halogen, or substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and R₉ and R₁₀ are each hydrogen, halogen, or substituted or unsubstituted silyl, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and n is an integer of 2 or more;

##STR26## wherein X₃ and X₄ are each single bond, --O--, --S-- or substituted or unsubstituted alkylene and are the same or different, R₁₅ to R₂₂ are each hydrogen, halogen, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, R₂₃ and R₂₄ are each hydrogen, halogen, substituted or unsubstituted silyl, substituted or unsubstituted alkyl or substituted or unsubstituted aryl and are the same or different, and m is an integer of 2 or more.

19. An electrophotographic apparatus according to claim 18, wherein said at least one resin is polyarylate resin.

20. An electrophotographic apparatus according to claim 18, wherein said at least one resin is polycarbonate resin.

21. An electrophotographic apparatus according to claim 18, wherein said charging means is a contact charging means.