Granted Patent B2

US 6,849,367 · App. 10/242,485 · Granted Feb 1, 2005

Assignee: Ricoh Company, Ltd.

Abstract

Claims (198)

1. An electrophotographic photoconductor comprising:

a conductive support; and

a photoconductive layer disposed on the photoconductive support;

wherein the photoconductive layer contains an azo compound expressed by a general formula <<1>>:

ArN═N—Cp) n   general formula <<1>>

wherein in the general formula <<1>>, Ar expresses one of a substituted or non-substituted aromatic hydrocarbon group and heterocyclic ring aromatic series group which can be combined by way of a bonding group; Cp expresses a coupler residual group; n expresses an integer of one of 1, 2, 3, and 4; at least one of the Cp is a coupler residual group selected from one of the following general formulae <<2>>, <<3>>, and <<4>>:

wherein in the general formulae <<2>>, <<3>>, and <<4>>, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each expresses one of a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group; X represents one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aromatic series hydrocarbon group, a substituted or non-substituted heterocyclic ring group, and a substituted or non-substituted amino group; and Y represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group, and a —CO—Z— carbonyl group containing divalent organic residual group, in which Z represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, and a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group.

2. An electrophotographic photoconductor according to claim 1 , wherein the coupler residual group expressed by the general formula <<2>> in the azo compound is a coupler residual group expressed by a general formula <<5>>:

wherein in the general formula <<5>>, A 1 expresses one of a substituted or non-substituted aromatic series hydrocarbon group, and a substituted or non-substituted heterocyclic ring group; and m is an integer of 1 to 6.

3. An electrophotographic photoconductor according to claim 1 , wherein in the azo compound, at least one of the Cp is a coupler residual group expressed by the general formula <<6>>, when n is one of 2, 3, and 4:

wherein in the general formula <<6>>, Z 1 represents one of a hydrocarbon ring or a substituted hydrocarbon ring, and a heterocyclic ring group or a substituted heterocyclic ring group; R 14 is one of hydrogen, an alkyl group or a substituted alkyl group, and a phenyl group or a substituted phenyl group; Y 2 represents one of a hydrocarbon ring group or a substituted hydrocarbon ring, and a heterocyclic ring group or a substituted heterocyclic ring group.

4. An electrophotographic photoconductor according to claim 1 , wherein in the azo compound, at least one of the Cp is a coupler residual group selected from one of a general formula <<7>> and a general formula <<8>>, when n is one of 2, 3, and 4:

wherein in the general formulae <<7>> and <<8>>, W 1 represents an aromatic hydrocarbon divalent group or a heterocyclic ring divalent group having a nitrogen atom in a ring, wherein said rings may be substituted or non-substituted.

5. An electrophotographic photoconductor according to claim 1 , wherein the azo compound is a disazo compound expressed by a general formula <<9>>:

wherein in the general formula <<9>>, Ar represents one of a substituted or non-substituted aromatic series hydrocarbon group, and an aromatic series heterocyclic ring group which may be combined by way of a bonding group; Cp′ represents a coupler residual group; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each represents one of a hydrogen atom, alkyl group, alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group; X represents one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aromatic series hydrocarbon group, a substituted or non-substituted heterocyclic ring group, and a substituted or non-substituted amino group; n 1 expresses an integer of 1 or 2 and n 2 expresses an integer of 0 or 1.

6. An electrophotographic photoconductor according to claim 5 , wherein the disazo compound is a disazo compound expressed by a general formula <<10>>:

wherein in the general formula <<10>>, Cp′ represents a coupler residual group; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each represents one of a hydrogen atom, alkyl group, alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group; X represents one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aromatic series hydrocarbon group, a substituted or non-substituted heterocyclic ring group, and a substituted or non-substituted amino group; n 1 expresses an integer of 1 or 2; n 2 expresses an integer of 0 or 1.

7. An electrophotographic photoconductor according to claim 1 , wherein the azo compound is a disazo compound expressed by one of general formulae <<11>> and <<12>>:

wherein in the general formulae <<11>> and <<12>>, Ar represents one of a substituted or non-substituted aromatic series hydrocarbon group, and an aromatic series heterocyclic ring group which may be combined by way of a bonding group; Cp′ represents a coupler residual group; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each represents one of a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group; Y represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group, and carbonyl group containing divalent organic residual group expressed by —CO—Z—, in which Z represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, and a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group; and n 1 expresses an integer of 1 or 2; and n 2 expresses an integer of 0 or 1.

8. An electrophotographic photoconductor according to claim 7 , wherein the disazo compound is a disazo compound expressed by one of a general formulae <<13>> and <<14>>:

wherein in the general formulae <<13>> and <<14>>, Ar represents one of a substituted or non-substituted aromatic series hydrocarbon group, and an aromatic series heterocyclic ring group which may be combined by way of a bonding group; Cp′ represents a coupler residual group; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each represents one of a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group; Y represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group, and a carbonyl group containing divalent organic residual group expressed by —CO—Z—, in which Z represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, and a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group; and n 1 expresses an integer of 1 or 2; and n 2 expresses an integer of 0 or 1.

9. An electrophotographic photoconductor according to claim 1 , wherein the azo compound of the general formula <<1>> is an azo compound which is obtained by reacting a diazonium salts compound expressed by a general formula <<15>> to a coupler compound expressed by a general formula <<16>>:

ArN 2 ⊕Z ⊖ ) n   general formula <<15>>

H—Cp  general formula <<16>>

wherein in the general formulae <<15>> and <<16>>, Ar represents one of a substituted or non-substituted aromatic series hydrocarbon group, and an aromatic series heterocyclic ring group which may be combined by way of a bonding group; Cp represents a coupler residual group; Z— represents an anion function; and n expresses an integer of 1, 2, 3 and 4.

10. An electrophotographic photoconductor according to claim 1 , wherein the photoconductive layer is a single layer formed on a conductive support by one of directly and intervening an intermediate layer.

11. An electrophotographic photoconductor according to claim 10 , wherein the photoconductive layer further contains a charge transporting substance.

12. An electrophotographic photoconductor according to claim 11 , wherein the charge transporting substance is a stilbene compound expressed by a general formula <<17>>:

wherein in the general formula <<17>>, T 1 and T 2 each independently represents one of a substituted or non-substituted alkyl group, and a substituted or non-substituted aryl group; T 3 and T 4 each independently represents one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aryl group, and a heterocyclic ring group; T 1 and T 2 may form a ring with each other; Ar′ expresses one of a substituted or non-substituted aryl group, and a heterocyclic ring group.

13. An electrophotographic photoconductor according to claim 11 , wherein the charge transporting substance is a polymer.

14. An electrophotographic photoconductor according to claim 13 , wherein the polymer is at least one polymer selected from the group consisting of polycarbonate, polyurethane, polyester, and polyether.

15. An electrophotographic photoconductor according to claim 13 , wherein the polymer has a structure of triaryl amine.

16. An electrophotographic photoconductor according to claim 13 , wherein the charge transporting substance is a polycarbonate having a triaryl amine structure.

17. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (1D):

wherein in the formula (1D), R′ 1 , R′ 2 , and R′ 3 each independently expresses a substituted or non-substituted alkyl group or a halogen atom;

R′ 4 represents a hydrogen atom or a substituted or non-substituted alkyl group; R 1 and R 2 each represents a substituted or non-substituted aryl group; o, p, and q may each independently represents an integer of 0 to 4;

k and j each satisfies 0.1≦k≦1 and 0≦j≦0.9; n represents a repeating unit of 5 to 5000; and

X is one member selected from the group consisting of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), R 24 and R 25 each independently represents one of a substituted or non-substituted alkyl group, an aryl group, and a halogen atom; l and m each represents an integer of 0 to 4;

Y represents one of a single bond, a linear chain having a carbon atom number of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20, b represents an integer of 1 to 2000, and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

18. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (2D):

wherein in the formula (2D), R 3 and R 4 represent a substituted or non-substituted aryl group;

Ar 1 , Ar 2 , and Ar 3 each represents the same or different arylene group;

k and j each satisfies 0.1≦k≦1 and 0≦j≦0.9;

n represents a repeating unit of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), R 24 and R 25 each independently represents a substituted or non-substituted alkyl group, an aryl group or a halogen atom; each of l and m represents an integer of 0 to 4;

Y represents one of a single bond, a linear chain having a carbon atom number 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; R 26 and R 27 each represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

19. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (3D):

wherein in the formula (3D), R 5 and R 6 each represents a substituted or non-substituted aryl group;

Ar 4 , Ar 5 , and Ar 6 each represents a same or different arylene group;

k and j each satisfies 0.1≦k≦1 and 0≦j≦0.9;

n represents a repeating unit of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), R 24 and R 25 each independently represents a substituted or non-substituted alkyl group, an aryl group or a halogen atom; each of l and m represents an integer of 0 to 4;

Y represents one of a single bond, a linear chain having a carbon atom number 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in where Z represents an aliphatic divalent group), and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; and R 26 and R 27 each represents a substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

20. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (4D):

wherein in the formula (4D), each of R 7 and R 8 represents a substituted or non-substituted aryl group;

each of Ar 7 , Ar 8 , and Ar 9 represents the same or a different arylene group;

each of k and j satisfies 0.1—k≦1 and 0≦j≦0.9;

n represents a repeating unit of 5 to 5000;

r represents an integer of 1 to 5; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a substance expressed by the general formula (A):

wherein in the formula (A), R 24 and R 25 each independently represents a substituted or non-substituted alkyl group, an aryl group or a halogen atom; each of l and m represents an integer of 0 to 4; Y represents one of a single bond, a linear chain having a carbon atom number of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

21. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (5D):

wherein in the formula (5D), each of R 9 and R 10 represents one of a substituted and non-substituted aryl group;

each of Ar 10 , Ar 11 , and Ar 12 represents the same or a different arylene group; each of X 1 and X 2 represents one of a substituted or non-substituted ethylene group, and a substituted or non-substituted vinylene group;

each of k and j satisfies 0.1≦k≦1 and 0≦j≦0.9;

n represents a repeating unit numbers of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), R 24 and R 25 each independently represents one of a substituted or non-substituted alkyl group, an aryl group and a halogen atom; each of l and m represents an integer of 0 to 4; Y represents one of a single bond, a linear chain having carbon atom numbers of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24, R 25 , R 26 , and R 27 may be the same or may be different.

22. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (6D):

wherein in the formula (6D), each of R 11 , R 12 , R 13 and R 14 represents one of a substituted and a non-substituted aryl group;

each of Ar 13 , Ar 14 , Ar 15 and Ar 16 represents the same or a different arylene group;

each of Y 1 , Y 2 , and Y 3 represents one of a single bond, a substituted or non-substituted alkylene group, a substituted or non-substituted cyclo alkylene group, a substituted or non-substituted alkyl ether group, oxygen atom, sulfur atom, and a vinylene group, which may be the same or maybe different;

k and j each satisfies 0.1≦k≦1 and 0≦j≦0.9;

n represents a repeating unit number of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), R 24 and R 25 independently represents a substituted or non-substituted alkyl group, an aryl group or a halogen atom; each of l and m represents an integer of 0 to 4;

Y represents a one of a single bond, a linear chain having carbon atom numbers of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

23. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (7D):

wherein in the formula (7D), each of R 15 and R 16 represents a hydrogen atom, a substituted or non-substituted aryl group;

each of R 15 and R 16 may form a ring;

Ar 17 , Ar 18 and Ar 19 may each represents the same or a different arylene group;

k and j each satisfies 0.1—k≦1 and 0≦j≦0.9;

n represents a repeating unit of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), each of R 24 and R 25 independently represents a substituted or non-substituted alkyl group, an aryl group, or a halogen atom; each of l and m represents an integer of 0 to 4;

Y represents a one of a single bond, a linear chain having carbon atom numbers of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20, b represents an integer of 1 to 2000; and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

24. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (8D):

wherein in the formula (8D), R 17 represents a substituted or non-substituted aryl group; each of Ar 20 , Ar 21 , Ar 22 and Ar 23 represents the same or a different arylene group;

each of k and j satisfies 0.1≦k≦1 and 0≦j≦0.9;

n represents a repeating unit of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), each of R 24 and R 25 independently represents one of a substituted or non-substituted alkyl group, and an aryl group or a halogen atom; each of l and m represents an integer of 0 to 4;

Y represents one of a single bond, a linear chain having carbon atom numbers of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

25. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (9D):

wherein in the formula (9D), each of R 18 , R 19 , R 20 and R 21 represents a substituted or non-substituted aryl group;

each of Ar 24 , Ar 25 , Ar 26 , Ar 27 , and Ar 28 represents the same or a different arylene group;

each of k and j satisfies 0.1≦k≦1 and 0≦j≦0.9;

n represents a repeating unit of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), each of R 24 and R 25 independently represents one of a substituted or non-substituted alkyl group, and an aryl group or a halogen atom; each of l and m represents an integer of 0 to 4;

Y represents a one of a single bond, a linear chain having carbon atom numbers of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

26. An electrophotographic photoconductor according to claim 16 , wherein the polycarbonate having the triaryl amine structure is a charge transporting substance expressed by a general formula (10D):

wherein in the formula (10D), each of R 22 , and R 23 represents a substituted or non-substituted aryl group;

each of Ar 29 , Ar 30 , and Ar 31 represents the same or a different arylene group; each of k and j satisfies 0.1≦k≦1 and 0≦j≦0.9; n represents a repeating unit of 5 to 5000; and

X is one of an aliphatic divalent group, a divalent cycloaliphatic group, and a general formula (A):

wherein in the formula (A), each of R 24 and R 25 independently represents a substituted or non-substituted alkyl group, an aryl group or a halogen atom; each of l and m represents an integer of 0 to 4;

Y represents a one of a single bond, a linear chain having carbon atom numbers of 1 to 12, a branched alkylene or a cycloalkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO—, in which Z represents an aliphatic divalent group, and a divalent group expressed by a general formula (B):

wherein in the formula (B), a represents an integer of 1 to 20; b represents an integer of 1 to 2000; and each of R 26 and R 27 represents substituted or non-substituted alkyl group or aryl group, and

R 24 , R 25 , R 26 , and R 27 may be the same or may be different.

27. An electrophotographic photoconductor according to claim 16 , wherein a polycarbonate having a triaryl amine is a charge transporting substance expressed by a general formula (11D):

wherein in the formula (11D), each of Ar 32 , Ar 33 , Ar 35 and Ar 36 represents substituted or non-substituted arylene group;

Ar 34 represents a substituted or non-substituted aryl group;

Z represents arylene group or —Ar 37 —Za—Ar 37 —, in which Ar 37 represents substituted or non-substituted arylene group;

Za represents O, S, or an alkylene group;

each of R and R′ represents a linear chain or branched alkylene group or —O—;

h represents 0 or 1;

each of k and j satisfies 0.1≦k≦1 and 0≦j≦0.9; n represents a repeating unit of 5 to 5000; and

X is one of a substituted or non-substituted aliphatic divalent group, a substituted or non-substituted divalent cycloaliphatic group, a substituted or non-substituted aromatic series divalent group, a divalent group formed by bonding them, and a divalent group expressed by one of general formulae (A′), (F), and (G):

wherein in the formulae (A′), (F) and (G), each of R 24 , R 25 , R 55 and R 56 each independently represents a substituted or non-substituted alkyl group, a substituted or non-substituted aryl group or a halogen atom;

l and m may each independently represents an integer of 0 to 4;

each of s and t independently represents an integer of 0 to 3;

when R 24 , R 25 , R 55 and R 56 respectively has a plurality of elements, they may be the same or may be different; and

Y represents one of a single bond, a linear chain having a carbon atom number of 1 to 12, a branched alkylene or a cycloalkylene group, a divalent group formed of at least one alkylene group having a carbon atom number of 1 to 10 and at least one oxygen atom and sulfur atom, —O—, —S—, —SO—, SO 2 —, —CO—, —COO—, —CO—O—Z 1 —O—CO—, —CO—Z 2 —CO—, in which each of Z 1 and Z 2 is a substituted or non-substituted aliphatic divalent group, or substituted or non-substituted arylene group, and one of general formulae (B), and general formulae (H) to (N):

wherein in the formulae (B), (H) to (N), each of R 26 and R 27 independently represents one of a substituted or non-substituted alkyl group, and a substituted or non-substituted aryl group;

each of R 57 , R 58 and R 64 represents a halogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted alkoxy group, a substituted or non-substituted aryl group;

each of R 59 , R 60 , R 61 , R 62 and R 63 independently represents one of a hydrogen atom or halogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted alkoxy group, and a substituted or non-substituted aryl group;

R 58 and R 59 may be combined and form a carbon ring having a carbon numbers of 5 to 12;

each of R 65 and R 66 represents a single bond or an alkylene group having a carbon number of 1 to 4; a represents an integer of 1 to 20;

b represents an integer of 1 to 2000;

each of u and w is an integer of 0 to 4; and v represents 1 or 2; and

when each of the R 26 , R 27 , R 57 and R 64 has a plurality of elements, they may be the same or may be different.

28. An electrophotographic photoconductor according to claim 11 , wherein the photoconductive layer further contains an acceptor compound.

29. An electrophotographic photoconductor according to claim 28 , wherein the acceptor compound is a 2,3-diphenyl indene compound expressed by a general formula <<18>>:

wherein in the formula <<18>>, each of Q 1 , Q 2 , Q 3 and Q 4 is a one of a hydrogen atom, a halogen atom, a substituted or non-substituted alkyl group, a cyano group, and a nitro group; and each of Q 5 and Q 6 is one of a hydrogen atom, substituted or non-substituted aryl group, a cyano group, an alkoxy carbonyl group, and an aryl oxy carbonyl group.

30. An electrophotographic photoconductor according to claim 28 , wherein the photoconductive layer further contains a phenol compound.

31. An electrophotographic photoconductor according to claim 30 , wherein the phenol compound is a phenol compound expressed by a general formula <<19>>:

wherein in general formula <<19>>, each of E 1 to E 8 is one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted alkoxy carbonyl group, substituted or non-substituted aryl group, and a substituted or non-substituted alkoxy group.

32. An electrophotographic photoconductor comprising:

a conductive support;

a photoconductive layer which contains a charge generating substance and a charge transporting substance on the conductive support;

wherein the charge generating substance is an azo compound expressed by a following general formula <<1>>:

ArN═N—Cp) n   general formula <<1>>

wherein in the general formula <<1>>, Ar is a substituted or non-substituted aromatic series hydrocarbon group or an aromatic series heterocyclic ring group, which can be bonded by way of a bonding group; Cp is a coupler residual group; n represents an integer of any one of 1, 2, 3, and 4; and at least one of the Cp is a coupler residual group selected from one of a general formula <<2>>, general formula <<3>>, and general formula <<4>>:

wherein in the general formula <<2>>, the general formula <<3>>, and the general formula <<4>>, each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is one of a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group;

X represents one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aromatic series hydrocarbon group, a substituted or non-substituted heterocyclic ring group, and a substituted or non-substituted amino group; and

Y represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group, and a carbonyl group containing divalent organic residual group expressed by —CO—Z—, in which Z represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, and a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group.

33. An azo compound comprising an azo compound expressed by a general formula <<1′>>, wherein at least one of the Cp is a coupler residual group selected from following general formulae <<2′>>, <<3′>> and <<4′>>:

ArN═N—Cp) n   general formula <<1′>>

wherein in the formula <<1′>>, Ar expresses one of a substituted or non-substituted aromatic hydrocarbon group, and an heterocyclic ring aromatic series group, which can be combined by way of a bonding group; and Cp expresses a coupler residual group; n expresses an integer of any of 1, 2, 3, and 4,

wherein in the formulae <<2′>>, <<3′>> and <<4′>>, each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is one of a hydrogen atom, an alkyl group, an alkoxy group, and a halogen atom;

X represents one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aromatic series hydrocarbon group, and a substituted or non-substituted heterocyclic ring group; and

Y represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group, and a —CO—Z— carbonyl group containing divalent organic residual group, in which Z represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, and a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group.

34. An azo compound according to claim 33 , wherein in the general formula <<1′>>, at least one of the Cp is a coupler residual group expressed by a general formula <<5′>>:

wherein in the general formula <<5′>>, A 1 represents one of a substituted or non-substituted aromatic series hydrocarbon group, and a substituted or non-substituted heterocyclic ring group; where m is an integer of 1 to 6.

35. An azo compound according to claim 33 , wherein in the general formula <<1′>>, at least one of the Cp is a coupler residual group expressed by a general formula <<6′>> when n is one of 2, 3 and 4:

wherein in general formula <<6′>>, Z 1 represents one of a hydrocarbon ring or a substituted hydrocarbon ring, and a heterocyclic ring group or a substituted heterocyclic ring group; R 14 is one of hydrogen, an alkyl group or a substituted alkyl group, and a phenyl group or a substituted phenyl group; and Y 2 represents one of a hydrocarbon ring group or a substituted hydrocarbon ring, and a heterocyclic ring group or a substituted heterocyclic ring group.

36. An electrophotographic photoconductor according to claim 33 , wherein in the general formula <<1′>>, at least one of the Cp is a coupler residual group selected by one of a general formulae <<7>> and <<8>>, when n is one of 2, 3, and 4:

wherein in the general formula <<7>> and <<8>>, W1 represents an aromatic series hydrogen divalent group or a heterocyclic ring divalent group including a nitrogen atom in a ring, wherein these rings may be substituted or non-substituted.

37. An apparatus for forming an image comprising:

an electrophotographic photoconductor;

means for charging an electrophotographic photoconductor;

means for exposing the electrophotographic photoconductor charged by the means for charging and forming a latent electrostatic image;

means for developing the latent electrostatic image, visualizing the latent electrostatic image, and forming a developed image; and

means for transferring the developed image formed by the means for developing onto a transferring substance,

wherein the electrophotographic photoconductor comprises a photoconductive layer which contains an azo compound expressed by a general formula <<1>> on a photoconductive layer:

ArN═N—Cp) n   general formula <<1>>

wherein in the general formula <<1>>, Ar expresses one of a substituted or non-substituted aromatic hydrocarbon group, and an heterocyclic ring aromatic series group which can be combined by way of a bonding group; Cp expresses a coupler residual group; n expresses an integer of any one of 1, 2, 3, and 4, wherein at least one of the Cp is a coupler residual group selected from general formulae <<2>>, <<3>>, and <<4>>:

wherein in the general formulae <<2>>, <<3>>, and <<4>>, each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is one of a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group;

X represents a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aromatic series hydrocarbon group, a substituted or non-substituted heterocyclic ring group, and a substituted or non-substituted amino group; and

Y represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group, and a carbonyl group containing divalent organic residual group expressed by —CO—Z—, in which Z represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, and a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group.

38. A process cartridge freely attachable and detachable to an apparatus for forming an image, comprising an electrophotographic photoconductor and at least one means selected from: means for charging; means for image exposing; means for developing; means for transferring; and means for cleaning,

wherein the electrophotographic photoconductor comprises a photoconductive layer which contains an azo compound expressed by a general formula <<1>> formed on a conductive support:

ArN═N—Cp) n   general formula <<1>>

wherein in the general formula <<1>>, Ar expresses one of a substituted or non-substituted aromatic hydrocarbon group, and an heterocyclic ring aromatic series group which can be combined by way of a bonding group; and Cp expresses a coupler residual group; n expresses an integer of any one of 1, 2, 3, and 4, wherein at least one of the Cp is a coupler residual group selected from general formulae <<2>>, <<3>>, and <<4>>:

wherein in the general formulae <<2>>, <<3>>, and <<4>>, each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is one of a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, an amino group, a hydroxy group, a nitro group, and a cyano group;

X represents one of a hydrogen atom, a substituted or non-substituted alkyl group, a substituted or non-substituted aromatic series hydrocarbon group, a substituted or non-substituted heterocyclic ring group, and a substituted or non-substituted amino group; and

Y represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group, and a carbonyl group containing divalent organic residual group expressed by —CO—Z—, in which Z represents one of a substituted or non-substituted alkylene group, a substituted or non-substituted aromatic series divalent organic residual group, and a substituted or non-substituted heterocyclic ring aromatic series divalent organic residual group.

Assignments (1)

Priority Claims (10)

Continuity (1)