US4427753A — Electrophotographic photosensitive member with di…

Claim 1

Independent Claim 103 words

An electrophotographic photosensitive member comprising a conductive support and overlying said support a layer comprising a binder and at least one azo pigment represented by the following formula (I) ##STR102## in the formula, Cp is a coupler residue; A 1 and A 2 are each a divalent organic residue; n is 0 or 1; and when n is 0, A 3 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or --(CH═CH) l --R', wherein R' is a substituted or unsubstituted heterocyclic ring residue and l is 0, 1 or 2, and when n is 1, A 3 is a divalent organic residue.

Claim 2

Dependent Claim 103 words

An electrophotographic photosensitive member comprising a conductive support and overlying said support a layer comprising a binder and at least one azo pigment represented by the following formula (I) ##STR102## in the formula, Cp is a coupler residue; A 1 and A 2 are each a divalent organic residue; n is 0 or 1; and when n is 0, A 3 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or --(CH═CH) l --R', wherein R' is a substituted or unsubstituted heterocyclic ring residue and l is 0, 1 or 2, and when n is 1, A 3 is a divalent organic residue.

Claim 3

Dependent Claim 53 words

An electrophotographic photosensitive member of claim 1, wherein A 1 and A 2 of the azo pigment represented by the formula (I) are a substituted or unsubstituted arylene group, or a conjugated double bond-containing divalent organic residue having at least one benzene ring which is condensed or not condensed with a heterocyclic ring.

Claim 4

Dependent Claim 54 words

An electrophotographic photosensitive member of claim 1, wherein A 3 of the azo pigment represented by the formula (I), when n is 1, is a substituted or unsubstituted arylene group or a conjugated double bond-containing divalent organic residue having at least one benzene ring which is condensed or not condensed with a heterocyclic ring.

Claim 5

Dependent Claim 111 words

An electrophotographic photosensitive member of claim 1, wherein said coupler residue Cp is represented by the following formula (1), (2), (3), or (4): ##STR103## in the formulae, X is an atomic group necessary to complete a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring; Y is hydrogen, ##STR104## or --COOR 4 , wherein R 3 is hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl and R 4 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic ring residue, or substituted or unsubstituted amino; and R 1 and R 2 each is substituted or unsubstituted alkyl or substituted or unsubstituted aryl.

Claim 6

Dependent Claim 41 words

An electrophotographic photosensitive member of claim 4, wherein said coupler residue Cp is represented by the formula: ##STR105## where R 4 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic ring residue, or substituted or unsubstituted amino.

Claim 7

Dependent Claim 35 words

An electrophotographic photosensitive member of claim 5, wherein said R 4 is a residue selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, phenyl, α-naphthyl, β-naphthyl, 4-chlorophenyl, 3-nitrophenyl, 2,5-dimethoxy-4-chlorophenyl, 4-methoxyphenyl, 2-pyridyl, 3-carbazolyl, and diphenylamino.

Claim 8

Dependent Claim 33 words

An electrophotographic photosensitive member of claim 4, wherein said R 1 and R 2 each are a residue selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, and 3-ethoxypropyl.

Claim 9

Dependent Claim 55 words

An electrophotographic photosensitive member of claim 2, wherein said azo pigment is a disazo pigment represented by the formula: ##STR106## wherein, Cp is a coupler residue; Ph 1 and Ph 2 each are a substituted or unsubstituted arylene group; and R is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

Claim 10

Dependent Claim 21 words

An electrophotographic photosensitive member of claim 8, wherein Ph 1 and Ph 2 each are a substituted or unsubstituted phenylene group.

Claim 11

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 9, wherein said phenylene group is p-phenylene.

Claim 12

Dependent Claim 74 words

An electrophotographic photosensitive member of claim 2, wherein said azo pigment is disazo pigment represented by the formula ##STR107## wherein Cp is a coupler residue; X 1 and X 2 each are a substituted or unsubstituted divalent organic residue of aromatic heterocyclic ring condensed with benzene or naphthalene ring; R is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; and p and q each are 0, 1, or 2.

Claim 13

Dependent Claim 51 words

An electrophotographic photosensitive member of claim 11, wherein said X 1 and X 2 each are a divalent residue of a heterocyclic compound selected from the group consisting of benzimidazole, naphthoimidazole, benzoxazole, isobenzoxazole, naphthoxazole, benzothiazole, naphthothiazole, benzoselenazole, naphthoselenazole, indole, quinoline, isoquinoline, benzofuran, dibenzofuran, coumalin, carbazole, phenothiazine, phenoxazine, and their substituted derivatives.

Claim 14

Dependent Claim 39 words

An electrophotographic photosensitive member of claim 12, wherein said X 1 and X 2 each are a divalent residue of a heterocyclic compound selected from the group consisting of carbazole, benzoxazole, dibenzofuran, benzimidazole, benzothiazole, indole, and their substituted derivatives.

Claim 15

Dependent Claim 22 words

An electrophotographic photosensitive member of claim 13, X 1 and X 2 each are a divalent residue of substituted or unsubstituted carbazole.

Claim 16

Dependent Claim 15 words

An electrophotographic photosensitive member of claim 11, wherein both said p and q represent zero.

Claim 17

Dependent Claim 55 words

An electrophotographic photosensitive member of claim 2, wherein said azo pigment is a disazo pigment represented by the formula ##STR108## wherein, Cp is a coupler residue; Ph 1 and Ph 2 each are a substituted or unsubstituted arylene group; R' is a substituted or unsubstituted heterocyclic ring residue; and l is 0, 1, or 2.

Claim 18

Dependent Claim 22 words

An electrophotographic photosensitive member of claim 16, wherein said Ph 1 and Ph 2 each are a substituted or unsubstituted phenylene group.

Claim 19

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 17, wherein said phenylene is p-phenylene.

Claim 20

Dependent Claim 53 words

An electrophotographic photosensitive member of claim 16, wherein said R' is a monovalent residue of a heterocyclic compound selected from the group consisting of imidazoline, imidazole, benzimidazole, naphthoimidazole, oxazoline, oxazole, benzoxazole, naphthoxazole, thiazoline, thiazole, benzothiazole, naphthothiazole, selenazole, benzoselenazole, naphthoselenazole, indoline, indole, pyridine, quinoline, furan, dibenzofuran, oxadiazole, thiadiazole, triazole, carbazole, and their substituted derivatives.

Claim 21

Dependent Claim 19 words

An electrophotographic photosensitive member of claim 16, wherein said R' is a substituted or unsubstituted nitrogen-containing heterocyclic ring residue.

Claim 22

Dependent Claim 36 words

An electrophotographic photosensitive member of claim 20, wherein said R' is a monovalent residue of a nitrogen-containing heterocyclic compound selected from the group consisting of pyridine, quinoline, carbazole, benzoxazole, benzothiazole, benzimidazole, indole, and their substituted derivatives.

Claim 23

Dependent Claim 15 words

An electrophotographic photosensitive member of claim 21, wherein said R' is substituted or unsubstituted carbazolyl.

Claim 24

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 16, wherein said l is zero.

Claim 25

Dependent Claim 72 words

An electrophotographic photosensitive member of claim 2, wherein said azo pigment is a disazo pigment represented by the formula ##STR109## wherein Cp is a coupler residue; Ph 3 , Ph 4 , Ph 5 , and Ph 6 each are a substituted or unsubstituted arylene group; Q 1 and Q 2 each are --CH═CH-- or ##STR110## R' is a substituted or unsubstituted heterocyclic ring residue; and l is 0, 1, or 2.

Claim 26

Dependent Claim 26 words

An electrophotographic photosensitive member of claim 24, wherein said Ph 3 , Ph 4 , Ph 5 and Ph 6 each are substituted or unsubstituted phenylene.

Claim 27

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 25, wherein said phenylene is p-phenylene.

Claim 28

Dependent Claim 52 words

An electrophotographic photosensitive member of claim 24, wherein said R' is a monovalent residue of a heterocyclic compound selected from the group consisting of imidazole, benzimidazole, naphthoimidazole, oxazoline, oxazole, benzoxazole, naphthoxazole, thiazoline, thiazole, benzothiazole, naphthothiazole, selenazole, benzoselenazole, naphthoselenazole, indoline, indole, pyridine, quinoline, furan, dibenzofuran, oxadiazole, thiadiazole, triazole, carbazole, and their substituted derivatives.

Claim 29

Dependent Claim 21 words

An electrophotographic photosensitive member of claim 24, wherein said R' is a monovalent residue of substituted or unsubstituted nitrogen-containing heterocyclic ring.

Claim 30

Dependent Claim 35 words

An electrophotographic photosensitive member of claim 28, wherein said R' is a monovalent residue of a heterocyclic compound selected from the group consisting of pyridine, quinoline, carbazole, benzoxazole, benzothiazole, benzimidazole, indole, and their substituted derivatives.

Claim 31

Dependent Claim 16 words

An electrophotographic photosensitive member of claim 29, wherein said R' is a substituted or unsubstituted carbazolyl.

Claim 32

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 24, wherein said l is zero.

Claim 33

Dependent Claim 17 words

An electrophotographic photosensitive member of claim 24, wherein said Q 1 and Q 2 each are --CH═CH--.

Claim 34

Dependent Claim 71 words

An electrophotographic photosensitive member of claim 2, wherein said azo pigment is a disazo pigment represented by the formula ##STR111## wherein Cp is a coupler residue; Ph 3 , Ph 4 , Ph 5 and Ph 6 each are a substituted or unsubstituted arylene group; Q 1 and Q 2 each are --CH═CH-- or ##STR112## and R is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

Claim 35

Dependent Claim 28 words

An electrophotographic photosensitive member of claim 33, wherein said Ph 3 , Ph 4 , Ph 5 and Ph 6 each are a substituted or unsubstituted phenylene group.

Claim 36

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 34, wherein said phenylene group is p-phenylene.

Claim 37

Dependent Claim 17 words

An electrophotographic photosensitive member of claim 33, wherein said Q 1 and Q 2 each are --CH═CH--.

Claim 38

Dependent Claim 43 words

An electrophotographic photosensitive member of claim 3, wherein said azo pigment is a trisazo pigment represented by the formula ##STR113## wherein Cp is a coupler residue; and Ph 1 , Ph 2 and Ph 7 each are a substituted or unsubstituted arylene group.

Claim 39

Dependent Claim 25 words

An electrophotographic photosensitive member of claim 37, wherein said Ph 1 , Ph 2 and Ph 7 each are a substituted or unsubstituted phenylene group.

Claim 40

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 38, wherein said phenylene group is p-phenylene.

Claim 41

Dependent Claim 69 words

An electrophotographic photosensitive member of claim 3, wherein said azo pigment is a trisazo pigment represented by the formula ##STR114## wherein, Cp is a coupler residue; X 1 and X 2 each are a substituted or unsubstituted divalent residue of aromatic heterocyclic ring condensed with a benzene or naphthalene ring; Ph 7 is a substituted or unsubstituted arylene group; and p and q each are 0, 1, or 2.

Claim 42

Dependent Claim 51 words

An electrophotographic photosensitive member of claim 40, wherein said X 1 and X 2 each are a divalent residue of a heterocyclic compound selected from the group consisting of benzimidazole, naphthimidazole, benzoxazole, isobenzoxazole, naphthoxazole, benzothiazole, naphthothiazole, benzoselenazole, naphthoselenazole, indole, quinoline, isoquinoline, benzofuran, dibenzofuran, coumalin, carbazole, phenothiazine, phenoxazine, and their substituted derivative.

Claim 43

Dependent Claim 39 words

An electrophotographic photosensitive member of claim 41, wherein said X 1 and X 2 each are a divalent residue of a heterocyclic compound selected from the group consisting of carbazole, benzoxazole, dibenzofuran, benzimidazole, benzothiazole, indole, and their substituted derivatives.

Claim 44

Dependent Claim 24 words

An electrophotographic photosensitive member of claim 42, wherein said X 1 and X 2 each are a divalent residue of substituted or unsubstituted carbazole.

Claim 45

Dependent Claim 18 words

An electrophotographic photosensitive member of claim 40, wherein said Ph 7 is a substituted or unsubstituted phenylene group.

Claim 46

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 44, wherein said phenylene group is p-phenylene.

Claim 47

Dependent Claim 81 words

An electrophotographic photosensitive member of claim 3, wherein said azo pigment is a trisazo pigment represented by the formula ##STR115## wherein Cp is a coupler residue; Ph 1 and Ph 2 each are a substituted or unsubstituted arylene group; Z 1 is --S--, --O--, --Se--, >N--R 6 , ##STR116## or --CH═CH--, each of R 6 , R 7 and R 8 being a hydrogen atom, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl; and l is 0, 1, or 2.

Claim 48

Dependent Claim 22 words

An electrophotographic photosensitive member of claim 46, wherein said Ph 1 and Ph 2 each are a substituted or unsubstituted phenylene group.

Claim 49

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 47, wherein said phenylene group is p-phenylene.

Claim 50

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 46, wherein said l is zero.

Claim 51

Dependent Claim 69 words

An electrophotographic photosensitive member of claim 3, wherein said azo pigment is a trisazo pigment represented by the formula ##STR117## wherein Cp is a coupler residue; Ph 1 and Ph 2 each are a substituted or unsubstituted arylene group; Z 2 is --O--, >N--R 9 , >C═O or ##STR118## R 9 being a hydrogen atom or a substituted or unsubstituted alkyl group; and l is 0, 1, or 2.

Claim 52

Dependent Claim 22 words

An electrophotographic photosensitive member of claim 50, wherein said Ph 1 and Ph 2 each are a substituted or unsubstituted phenylene group.

Claim 53

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 51, wherein said phenylene group is p-phenylene.

Claim 54

Dependent Claim 28 words

An electrophotographic photosensitive member of claim 50, wherein said Z 2 is >N--R 9 , R 9 being a hydrogen atom or a substituted or unsubstituted alkyl group.

Claim 55

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 50, wherein said l is zero.

Claim 56

Dependent Claim 59 words

An electrophotographic photosensitive member of claim 3, wherein said azo pigment is a trisazo pigment represented by the formula ##STR119## wherein, Cp is a coupler residue, Ph 3 , Ph 4 , Ph 5 , Ph 6 and Ph 7 each are a substituted or unsubstituted arylene group, and Q 1 and Q 2 each are --CH═CH-- or ##STR120##

Claim 57

Dependent Claim 31 words

An electrophotographic photosensitive member of claim 55, wherein said Ph 3 , Ph 4 , Ph 5 , Ph 6 and Ph 7 each are a substituted or unsubstituted phenylene group.

Claim 58

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 56, wherein said phenylene group is p-phenylene.

Claim 59

Dependent Claim 94 words

An electrophotographic photosensitive member of claim 3, wherein said azo pigment is a trisazo pigment represented by the formula ##STR121## wherein, Cp is a coupler residue; Ph 3 , Ph 4 , Ph 5 and Ph 6 each are a substituted or unsubstituted arylene group; Q 1 and Q 2 each are --CH═CH-- or ##STR122## Z is --S--, --O--, --Se--, >N--R 6 , ##STR123## or --CH═CH--, R 6 , R 7 and R 8 being a hydrogen atom, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl; and l is 0, 1 or 2.

Claim 60

Dependent Claim 28 words

An electrophotographic photosensitive member of claim 58, wherein said Ph 3 , Ph 4 , Ph 5 and Ph 6 each are a substituted or unsubstituted phenylene group.

Claim 61

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 59, wherein said phenylene group is p-phenylene.

Claim 62

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 58, wherein said l is zero.

Claim 63

Dependent Claim 84 words

An electrophotographic photosensitive member of claim 3, wherein said azo pigment is a trisazo pigment represented by the formula ##STR124## wherein, Cp is a coupler residue; Ph 3 , Ph 4 , Ph 5 and Ph 6 each are a substituted or unsubstituted arylene group; Q 1 and Q 2 each are --CH═CH-- or ##STR125## Z 2 is --O--, >N--R 9 , >C═O, or ##STR126## R 9 being a hydrogen atom or a substituted or unsubstituted alkyl; and l is 0, 1, or 2.

Claim 64

Dependent Claim 28 words

An electrophotographic photosensitive member of claim 62, wherein said R 3 , R 4 , R 5 and R 6 each are a substituted or unsubstituted phenylene group.

Claim 65

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 63, wherein said phenylene group is p-phenylene.

Claim 66

Dependent Claim 27 words

An electrophotographic photosensitive member of claim 62, wherein said Z 2 is >N--R 9 , R 9 being a hydrogen atom or a substituted or unsubstituted alkyl.

Claim 67

Dependent Claim 12 words

An electrophotographic photosensitive member of claim 62, wherein said l is zero.

Claim 68

Dependent Claim 100 words

An electrophotographic photosensitive member comprising (i) a charge generation layer comprising an azo pigment represented by the following formula (I): ##STR127## in the formula, Cp is a coupler residue; A 1 and A 2 are each a divalent organic residue; n is 0 or 1; and when n is 0, A 3 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or --(CH═CH) l --R', wherein R' is a substituted or unsubstituted heterocyclic ring residue and l is 0, 1 or 2, and when n is 1, A 3 is a divalent organic residue and (ii) a charge transport layer.

Claim 69

Dependent Claim 100 words

An electrophotographic photosensitive member comprising (i) a charge generation layer comprising an azo pigment represented by the following formula (I): ##STR127## in the formula, Cp is a coupler residue; A 1 and A 2 are each a divalent organic residue; n is 0 or 1; and when n is 0, A 3 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or --(CH═CH) l --R', wherein R' is a substituted or unsubstituted heterocyclic ring residue and l is 0, 1 or 2, and when n is 1, A 3 is a divalent organic residue and (ii) a charge transport layer.

Claim 70

Dependent Claim 19 words

An electrophotographic photosensitive member of claim 67, wherein said charge transport layer is laid on the charge generation layer.

Claim 71

Dependent Claim 15 words

An electrophotographic photosensitive member of claim 68, said charge transport layer contains a hole-transporting material.

Claim 72

Dependent Claim 29 words

An electrophotographic photosensitive member of claim 69, wherein said hole-transporting material is a compound selected from the group consisting of pyrazoline compounds, oxadiazole compounds, arylalkane compounds, and hydrazone compounds.

Claim 73

Dependent Claim 15 words

An electrophotographic photosensitive member of claim 70, wherein said hole-transporting material is a hydrazone compound.

Claim 74

Dependent Claim 16 words

An electrophotographic photosensitive member of claim 68, wherein said charge transport layer contains an electron-transporting material.

Claim 75

Dependent Claim 30 words

An electrophotographic photosensitive member of claim 72, wherein said electron-transporting material is a compound selected from the group consisting of chloranil, bromanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetrahydrofluorenone, 2,4,7-trinitro-9-dicyanomethylenefluorenone, 2,4,5,7-tetranitroxanthone, and 2,4,8-trinitrothioxanthone.

Claim 76

Dependent Claim 76 words

An electrophotographic photosensitive member comprising a photosensitive layer comprising (i) at least one azo pigment represented by the following formula (I): ##STR128## in the formula, Cp is a coupler residue; A 1 and A 2 are each a divalent organic residue; n is 0 or 1; and wherein R' is a substituted or unsubstituted heterocyclic ring residue and l is 0, 1 or 2, and when n is 1, A 3 is a divalent organic residue.

Claim 77

Dependent Claim 76 words

An electrophotographic photosensitive member comprising a photosensitive layer comprising (i) at least one azo pigment represented by the following formula (I): ##STR128## in the formula, Cp is a coupler residue; A 1 and A 2 are each a divalent organic residue; n is 0 or 1; and wherein R' is a substituted or unsubstituted heterocyclic ring residue and l is 0, 1 or 2, and when n is 1, A 3 is a divalent organic residue.

Claim 78

Dependent Claim 13 words

An electrophotographic photosensitive member of claim 74, wherein said hole-transporting material is poly(N-vinylcarbazole).

Claim 79

Dependent Claim 22 words

An electrophotographic photosensitive member of claim 75, wherein said hole-transporting material is a charge transfer complex of poly(N-vinylcarbazole) and a fluorenone compound.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1987-01-23	1987-07-25	1988-01-24	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1991-01-23	1991-07-25	1992-01-24	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1995-01-23	1995-07-25	1996-01-24	$7700.00	Window Closed / Lapsed

Electrophotographic photosensitive member with disazo or trisazo compound

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