Photoconductive compositions containing novel disazo compounds and electrophotographic photoreceptors using the same

Claim 2

A photoconductive composition comprising disazo compound represented by the general formula (1) ##STR31## wherein B 1 and B 2 each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, an aryl group, an aryloxy group, an aryloxycarbonyl group, or a substituted group thereof; Z is ##STR32## R 6 is a hydrogen atom, a lower alkyl group, an aryl group, an aryloxy group, an aryloxycarbonyl group or a substituted group thereof; A represents ##STR33## X represents a group of atoms which links with the benzene ring to which the hydroxyl group and the Y group are attached to form an aromatic ring or a heterocyclic ring which may be substituted or unsubstituted; Y represents ##STR34## R 1 is an alkyl group, a phenyl group, or a substituted group thereof; R 2 is a hydrogen atom, a lower alkyl group, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a substituted or unsubstituted amino group; R 3 and R 5 each represents an alkyl group, an aromatic group or a heterocyclic group, or a substituted group thereof; and R 4 is a hydrogen atom, an alkyl group, a phenyl group or a substituted group thereof.

Claim 3

The photoconductive disazo compound of claim 1, wherein the lower alkyl group for R 6 is methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, isohexyl, neopentyl or tert-butyl and the substituents on the alkyl group for R 6 can be one or more of a hydroxyl group, an alkoxyl group of 1 to 6 carbon atoms, a cyano group, an alkylamino group of 1 to 6 carbon atoms, a dialkylamino group having two alkyl groups of 1 to 6 carbon atoms, a halogen atom or an aryl group of 6 to 15 carbon atoms, said unsubstituted aryl group for R 6 is phenyl or naphthyl, said unsubstituted aryloxy group for R 6 is phenoxy or naphthoxy, said unsubstituted aryloxycarbonyl group for R 6 is phenoxycarbonyl or naphthoxycarbonyl, and when R 6 is a substituted aryl group, a substituted aryloxy group or substituted aryloxycarbonyl group, the substituent group may be the same as defined for the substituted alkyl group for R 6 .

Claim 4

The photoconductive disazo compound of claim 1, wherein the substituted aromatic ring or heterocyclic ring for X contains one or more of a halogen atom or a lower alkyl group as a substituent.

Claim 5

The photoconductive disazo compound of claim 1, wherein the alkyl group for R 1 is methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, isoamyl, isohexyl, neopentyl, or tert-butyl; and the substituted alkyl group for R 1 is an alkyl group substituted with one or more of a hydroxyl group, alkoxy group of 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group of 1 to 12 carbon atoms, a dialkylamino group with two alkyl groups of 1 to 12 carbon atoms, a halogen atom or an aryl group of 6 to 15 carbon atoms; the substituted phenyl group for R 1 is a phenyl group substituted with one or more of a hydroxy group, an alkoxy group of 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group of 1 to 12 carbon atoms, a dialkylamino group having two alkyl groups of 1 to 12 carbon atoms, a halogen atom, an alkyl group of 1 to 6 carbon atoms and a nitro group.

Claim 6

The photoconductive disazo compound of claim 1, wherein the lower alkyl group for R 2 is methyl, ethyl, propyl, butyl, isopropyl or isobutyl, the alkoxycarbonyl group for R 2 contains an alkoxy moiety of 1 to 12 carbon atoms, the aryloxycarbonyl group for R 2 contains an aryloxy group of 6 to 20 carbon atoms and the substituted amino group for R 2 is methylamino, ethylamino, propylamino, phenylamino, tolylamino, benzylamino, phenethylamino, dimethylamino, diethylamino or diphenylamino.

Claim 7

The photoconductive disazo compound of claim 1, wherein the alkyl group for R 3 and R 5 is an alkyl group of 1 to 20 carbon atoms, the aromatic groups for R 3 and R 5 is a phenyl group or a naphthyl group, the heterocyclic group for R 3 and R 5 is a heterocyclic group containing one or more of oxygen, nitrogen or sulfur hetero atoms and the substituted alkyl for R 3 and R 5 is an alkyl group substituted with one or more of a hydroxy group, an alkoxy group of 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group of 1 to 12 carbon atoms, a dialkylamino group with alkyl groups of 1 to 12 carbon atoms, a halogen atom and an aryl group of 6 to 15 carbon atoms, and the substituted aromatic group for R 3 and R 5 is substituted with one or more of a hydroxyl group, a cyano group, a nitro group, a halogen atom, an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 12 carbon atoms, an amino group, an alkylamino group of 1 to 12 carbon atoms, a dialkylamino group having two alkyl groups of 1 to 12 carbon atoms, an arylamino group of 6 to 12 carbon atoms, a diarylamino group of 6 to 15 carbon atoms, a carboxyl group, an alkali metal carboxylate group, an alkali metal sulfonate group, an alkylcarbonyl group, an arylcarbonyl group having an aryl group of 6 to 12 carbon atoms and an alkylthio group of 1 to 12 carbon atoms.

Claim 8

The photoconductive disazo compound of claim 1, wherein the alkyl group for R 4 is an alkyl group having 1 to 20 carbon atoms and the substituted alkyl group for R 4 is an alkyl group substituted with one or more of a hydroxyl group, an alkoxy group of 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group of 1 to 12 carbon atoms, a dialkylamino group with two alkyl groups of 1 to 12 carbon atoms, a halogen atom and an aryl group of 6 to 15 carbon atoms, and the substituted phenyl group for R 4 is a phenyl group substituted with one or more of a hydroxyl group, a cyano group, a nitro group, a halogen atom, an alkyl group of 1 to 12 carbon atoms, an alkoxyl group of 1 to 12 carbon atoms, an amino group, an alkylamino group of 1 to 12 carbon atoms, a dialkylamino group having two alkyl groups of 1 to 12 carbon atoms, an arylamino group of 6 to 12 carbon atoms, a diarylamino group having two aryl groups of 6 to 15 carbon atoms, a carboxyl group, an alkali metal carboxylate group, an alkali metal sulfonate group, an alkylcarbonyl group, an arylcarbonyl group having an aryl group of 6 to 12 carbon atoms, an alkylthio group of 1 to 12 carbon atoms and an arylthio group of one to 12 carbon atoms.

Claim 9

The photoconductive disazo compound of claim 1, wherein B 1 and B 2 each represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, an alkoxycarbonyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, an aryloxy group of 6 to 15 carbon atoms, or an aryloxycarbonyl group of 6 to 15 carbon atoms and the substituents for the alkyl, alkoxy, alkoxycarbonyl, aryl, aryloxy or aryloxycarbonyl groups are selected from the group consisting of one or more of a hydroxyl group, an alkoxyl group of 1 to 6 carbon atoms, a cyano group, an alkylamino group of 1 to 6 carbon atoms, a dialkylamino group having two alkyl groups of 1 to 6 carbon atoms, a halogen atom or an aryl group of 6 to 15 carbon atoms.

Claim 10

The photoconductive disazo compound of claim 1, wherein said compound represented by the general formula (1) has the general formula (2) ##STR35## wherein B 3 and B 4 each represents a hydrogen atom, a chlorine atom or a bromine atom; X' represents a benzene ring, a carbazole ring or a dibenzofuran ring; and R 4 and R 5 are as defined in the general formula (1).

Claim 11

An electrophotographic photoreceptor comprising an electrically conductive support and a photoconductive layer provided thereon which comprises a charge transporting substance and a charge generating substance, the charge generating substance being a disazo compound represented by the general formula (1) ##STR36## wherein B 1 and B 2 each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, an aryl group, an aryloxy group, an aryloxycarbonyl group, or a substituted group thereof; Z is ##STR37## R 6 is a hydrogen atom, a lower alkyl group, an aryl group, an aryloxy group, an aryloxycarbonyl group or a substituted group thereof; a represents ##STR38## X represents a group of atoms which links with the benzene ring to which the hydroxyl group and the Y groups are attached to form an aromatic or heterocyclic ring, which may be substituted or unsubstituted; Y represents ##STR39## R 1 is an alkyl group, a phenyl group, or a substituted group thereof; R 2 is a hydrogen atom, a lower alkyl group, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a substituted or unsubstituted amino group; R 3 and R 5 each represents an alkyl group, an aromatic group or a heterocyclic group, or a substituted group thereof; and R 4 is a hydrogen atom, an alkyl group, a phenyl group, or a substituted group thereof; on an electrically conductive support.

Claim 12

An electrophotographic photoreceptor comprising an electrically conductive support and a photoconductive layer provided thereon which comprises a charge transporting substance and a charge generating substance, the charge generating substance being a disazo compound represented by the general formula (1) ##STR36## wherein B 1 and B 2 each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, an aryl group, an aryloxy group, an aryloxycarbonyl group, or a substituted group thereof; Z is ##STR37## R 6 is a hydrogen atom, a lower alkyl group, an aryl group, an aryloxy group, an aryloxycarbonyl group or a substituted group thereof; a represents ##STR38## X represents a group of atoms which links with the benzene ring to which the hydroxyl group and the Y groups are attached to form an aromatic or heterocyclic ring, which may be substituted or unsubstituted; Y represents ##STR39## R 1 is an alkyl group, a phenyl group, or a substituted group thereof; R 2 is a hydrogen atom, a lower alkyl group, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a substituted or unsubstituted amino group; R 3 and R 5 each represents an alkyl group, an aromatic group or a heterocyclic group, or a substituted group thereof; and R 4 is a hydrogen atom, an alkyl group, a phenyl group, or a substituted group thereof; on an electrically conductive support.

Claim 13

The electrophotographic photoreceptor of claim 10, wherein the photoconductive layer comprises a single layer containing the charge transporting substance and the charge generating substance.

Claim 14

The electrophotographic photoreceptor of claim 10, wherein the photoconductive layer comprises at least two layers comprising a layer containing the charge transporting substance and a layer containing the charge generating substance.