Electrophotographic Photoconductor

• US 5,427,880 A
• Filed: 02/01/1994
• Issued: 06/27/1995
• Est. Priority Date: 02/01/1993
• Status: Expired due to Fees

• Current Assignee: Ricoh Company Limited
• Original Assignee: Ricoh Company Limited
• Inventors: Tamura, Hiroshi, Fukagai, Toshio
• Primary Examiner(s): MARTIN, ROLAND E
• Application Number:
  US08/189,605
• Time in Patent Office: 511 Days
• Field of Search: 430/59, 430/83
• US Class Current: 430/58.7
• CPC Class Codes: G03G 5/0546 Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides
• CPC Class Codes: G03G 5/056 Polyesters
• CPC Class Codes: G03G 5/0564 Polycarbonates
• CPC Class Codes: G03G 5/0567 Other polycondensates comprising oxygen atoms in the main chain; Phenol resins
• CPC Class Codes: G03G 5/0582 Polycondensates comprising sulfur atoms in the main chain
• CPC Class Codes: G03G 5/0592 Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity
• CPC Class Codes: G03G 5/071 obtained by reactions only involving carbon-to-carbon unsaturated bonds G03G5/078 takes precedence

Abstract

An electrophotographic photoconductor composed of an electroconductive substrate and a photoconductive layer formed thereon, containing an interpenetrating polymer network prepared by polymerizing a composition composed of a binder resin and at least one polymerizable carbon-carbon double-bond-containing charge transporting monomer selected from the group consisting of monomers of formulas (I), (II) and (III) by the application of light or heat thereto: ##STR1##

Claims

1. An electrophotographic photoconductor comprising an electroconductive substrate and a photoconductive layer formed thereon, wherein said photoconductive layer comprises a charge generating material and an interpenetrating polymer network prepared by polymerizing a composition comprising a binder resin and at least one polymerizable carbon-carbon double-bond-containing charge transporting monomer selected from the group consisting of monomers of formulas (I), (II) and (III) by the application of light or heat thereto:

##STR107## wherein R¹ is hydrogen or methyl group;

Ar¹ and Ar² each is a bivalent aromatic hydrocarbon group which may have a substituent such as hydrogen, fluorine, chlorine, bromine, iodine, or a straight-chain or branched alkyl group having 1 to 4 carbon atoms which may have a substituent such as fluorine, cyano group or phenyl group;

Ar³ and Ar⁴ each is a monovalent aromatic hydrocarbon group which may have a substituent such as hydrogen, fluorine, chlorine, bromine, iodine, or a straight-chain or branched alkyl group having 1 to 4 carbon atoms which may have a substituent such as fluorine, cyano group or phenyl group;

Y is --C_n H_2n --, --CH═

CH--, or --CAr¹ ═

CH--;

Z id --O--, --OC_n H_2n --, or --OC_n H_2n O--;

n is an integer from 1 to 10; and

m1 and m2 is an integer of 0 or 1.

2. The electrophotographic photoconductor as claimed in claim 1, wherein said binder resin is a homopolymer or copolymer comprising a repeat unit represented by formula (IV):

##STR108## wherein R⁶ and R⁷ each is hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group, and R⁶ and R7 may form a cycloalkyl group in combination;

R⁸, R⁹, R¹⁰ and R¹¹ each is hydrogen, an alkyl group having 1 to 5 carbon atoms, an aryl group, a cycloalkyl group or a halogen; and

X is ##STR109##

3. The electrophotographic photoconductor as claimed in claim 1, wherein said binder resin is a vinyl homopolymer or copolymer resin comprising a repeat unit represented by formula (V):

##STR110## wherein R¹ is hydrogen or methyl group; and

X is an aryl group or COOR², in which R² is an alkyl group having 1 to 3 carbon atoms or an aryl group.

4. The electrophotographic photoconductor as claimed in claim 1, wherein the amount ratio by weight of said charge transporting monomer to that of said binder resin in said composition is in the range from 10:

5 to 10;

50.

5. The electrophotographic photoconductor as claimed in claim 1, wherein said photoconductive layer comprises a charge generation layer comprising said charge generating material, and a charge transport layer formed on said charge generation layer, comprising said interpenetrating polymer network prepared by polymerizing said composition comprising said carbon-carbon double-bond-containing charge transporting monomer and said binder resin.

6. The electrophotographic photoconductor as claimed in claim 5, further comprising an intermediate layer which is provided between said electroconductive substrate and said charge generation layer.

7. The electrophotographic photoconductor as claimed in claim 5, wherein said binder resin for use in said interpenetrating polymer network is said homopolymer or copolymer comprising a repeat unit represented by formula (IV):

##STR111## wherein R⁶ and R⁷ each is hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group, and R⁶ and R7 may form a cycloalkyl group in combination;

R⁸, R⁹, R¹⁰ and R¹¹ each is hydrogen, an alkyl group having 1 to 5 carbon atoms, an aryl group, a cycloalkyl group or a halogen; and

X is ##STR112##

8. The electrophotographic photoconductor as claimed in claim 5, wherein said binder resin for use in said interpenetrating polymer network is said vinyl homopolymer or copolymer resin comprising a repeat unit represented by formula (V):

##STR113## wherein R¹ is hydrogen or methyl group; and

X is an aryl group or COOR², in which R² is an alkyl group having 1 to 3 carbon atoms or an aryl group.

9. The electrophotographic photoconductor as claimed in claim 1, wherein said photoconductive layer comprises a charge transport layer comprising a charge transporting material, and a charge generation layer formed on said charge transport layer, comprising an interpenetrating polymer network prepared by polymerizing a composition comprising said charge generating material, said carbon-carbon double-bond-containing charge transporting monomer and said binder resin.

10. The electrophotographic photoconductor as claimed in claim 9, wherein said binder resin for use in said interpenetrating polymer network is said homopolymer or copolymer comprising a repeat unit represented by formula (IV):

##STR114## wherein R⁶ and R⁷ each is hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group, and R⁶ and R7 may form a cycloalkyl group in combination;

R⁸, R⁹, R¹⁰ and R¹¹ each is hydrogen, an alkyl group having 1 to 5 carbon atoms, an aryl group, a cycloalkyl group or a halogen; and

X is ##STR115##

11. The electrophotographic photoconductor as claimed in claim 9, wherein said binder resin for use in said interpenetrating polymer network is said vinyl homopolymer or copolymer resin comprising a repeat unit represented by formula (V):

##STR116## wherein R¹ is hydrogen or methyl group; and

X is an aryl group or COOR², in which R² is an alkyl group having 1 to 3 carbon atoms or an aryl group.

12. The electrophotographic photoconductor as claimed in claim 9, wherein the amount ratio by weight of said charge transporting monomer to that of said binder resin to that of said charge generating material in said composition for said interpenetrating polymer network is 10:

(7 to

     30);

(2 to

     10).

13. The electrophotographic photoconductor as claimed in claim 1, wherein said composition for use in said interpenetrating polymer network comprises said charge generating material.

14. The electrophotographic photoconductor as claimed in claim 13, wherein said binder resin for use in said interpenetrating polymer network is said homopolymer or copolymer comprising a repeat unit represented by formula (IV):

##STR117## wherein R⁶ and R⁷ each is hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group, and R⁶ and R7 may form a cycloalkyl group in combination;

R⁸, R⁹, R¹⁰ and R¹¹ each is hydrogen, an alkyl group having 1 to 5 carbon atoms, an aryl group, a cycloalkyl group or a halogen; and

X is ##STR118##

15. The electrophotographic photoconductor as claimed in claim 13, wherein said binder resin for use in said interpenetrating polymer network is said vinyl homopolymer or copolymer resin comprising a repeat unit represented by formula (V):

##STR119## wherein R¹ is hydrogen or methyl group; and

X is an aryl group or COOR², in which R² is an alkyl group having 1 to 3 carbon atoms or an aryl group.

16. The electrophotographic photoconductor as claimed in claim 13, wherein the amount ratio by weight of said charge transporting monomer to that of said binder resin to that of said charge generating material in said composition is 10:

(7 to

     30);

(2 to

     10).

17. The electrophotographic photoconductor as claimed in claim 5, wherein said charge transport layer further comprises a low-molecular-weight charge transporting material.

18. The electrophotographic photoconductor as claimed in claim 17, wherein the amount ratio by weight of said carbon-carbon double-bond-containing charge transporting monomer to that of said low-molecular weight charge transporting material is in the range from (10:

0.1) to (10;

10).

19. The electrophotographic photoconductor as claimed in claim 17, wherein said charge transport layer is of a laminated type, comprising a top charge transport layer comprising said interpenetrating polymer network prepared by polymerizing said composition comprising said carbon-carbon double-bond-containing charge transporting monomer and said binder resin.