Patent US5407549A successfully refreshed from Google Patents.
US4399208A
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Electrophotographic photosensitive member
Assignee: Canon Inc
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Filing: 1981-11-09
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Granted: 1983-08-16
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Expires: 2001-11-09
Abstract
Abstract An electrophotographic photosensitive member is characterized by having a layer containing at least one hydrazone compound represented by the following formula [I] or [II]: ##STR1## wherein R 11 and R 12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R 11 and R 12 is substituted amino or alkoxy; R 13 and R 14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R 13 and R 14 is substituted or unsubstituted aryl, or R 13 and R 14 , together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; R 15 , R 16 , R 17 , and R 18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino; m and n represent 0 or 1; R 21 and R 22 represent substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 23 and R 24 represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or R 23 and R 24 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 25 and R 26 represent hydrogen, halogen, nitro, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted acyl, or substituted or unsubstituted amino; and R represents divalent organic residue.
Inventors
- 👤 Yoshio Takasu
- 👤 Norie Takebayashi
- 👤 Kiyoshi Sakai
- 👤 Minoru Mabuchi
- 👤 Shozo Ishikawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 12:06
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0664; G03G5/0666; G03G5/0672; G03G5/0674; C; C07; C07C; C07C251/00; C07C251/72; G03G5/0601; G03G5/0612; G03G5/0616; G03G5/0622; G03G5/0624; G03G5/0627; G03G5/0629; G03G5/0644; G03G5/0661; G03G5/0668
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
255 words
An electrophotographic photosensitive member characterized by having a conductive support and a layer containing at least one hydrazone compound represented by the following formula [I] or [II]: ##STR31## wherein R 11 and R 12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R 11 and R 12 is substituted amino or alkoxy; R 13 and R 14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R 13 and R 14 is substituted or unsubstituted aryl, or R 13 and R 14 , together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; R 15 , R 16 , R 17 , and R 18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino; m and n represent 0 or 1; R 21 and R 22 , represent substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 23 and R 24 represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or R 23 and R 24 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 25 and R 26 represent hydrogen, halogen, nitro, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted acyl, or substituted or unsubstituted amino; and R represents divalent organic residue.
Claim 2
Dependent Claim
255 words
An electrophotographic photosensitive member characterized by having a conductive support and a layer containing at least one hydrazone compound represented by the following formula [I] or [II]: ##STR31## wherein R 11 and R 12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R 11 and R 12 is substituted amino or alkoxy; R 13 and R 14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R 13 and R 14 is substituted or unsubstituted aryl, or R 13 and R 14 , together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; R 15 , R 16 , R 17 , and R 18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino; m and n represent 0 or 1; R 21 and R 22 , represent substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 23 and R 24 represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or R 23 and R 24 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 25 and R 26 represent hydrogen, halogen, nitro, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted acyl, or substituted or unsubstituted amino; and R represents divalent organic residue.
Claim 3
Dependent Claim
136 words
An electrophotographic photosensitive member according to claim 1, wherein said hydrazone compound is represented by the following formula (1): ##STR32## wherein, R 11 and R 12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R 11 and R 12 is substituted amino, or alkoxy; R 13 and R 14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R 13 and R 14 is substituted or unsubstituted aryl, or R 13 and R 14 , together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; and R 15 , R 16 , R 17 , and R 18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino.
Claim 4
Dependent Claim
22 words
An electrophotographic photosensitive member according to claim 2, wherein R 11 and R 12 are radicals selected from alkoxy and substituted amino.
Claim 5
Dependent Claim
18 words
An electrophotographic photosensitive member according to claim 3, wherein R 11 and R 12 are each substituted amino.
Claim 6
Dependent Claim
24 words
An electrophotographic photosensitive member according to claim 4, wherein R 11 and R 12 are radicals selected from N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-dibutylamino, and N,N-dibenzylamino.
Claim 7
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 5, wherein R 11 and R 12 are each diethylamino.
Claim 8
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 3, wherein R 11 and R 12 are each alkoxy.
Claim 9
Dependent Claim
21 words
An electrophotographic photosensitive member according to claim 7, wherein R 11 and R 12 are radicals selected from methoxy and ethoxy.
Claim 10
Dependent Claim
24 words
An electrophotographic photosensitive member according to claim 2, wherein R 15 , R 16 , R 17 , and R 18 are each hydrogen.
Claim 11
Dependent Claim
20 words
An electrophotographic photosensitive member according to claim 9, wherein at least one of R 13 and R 14 is phenyl.
Claim 12
Dependent Claim
19 words
An electrophotographic photosensitive member according to claim 10, wherein R 13 is a radical selected from methyl and ethyl.
Claim 13
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 10, wherein R 13 and R 14 are each phenyl.
Claim 14
Dependent Claim
26 words
An electrophotographic photosensitive member according to claim 2, wherein R 13 and R 14 , together with the nitrogen atom which links them, represent carbazole ring.
Claim 15
Dependent Claim
141 words
An electrophotographic photosensitive member according to claim 1, wherein said hydrazone compound is represented by the following formula (2): ##STR33## wherein R 11 and R 12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R 11 and R 12 is substituted amino or alkoxy; R 13 and R 14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R 13 and R 14 is substituted or unsubstituted aryl, or R 13 and R 14 , together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; R 15 , R 16 , R 17 , and R 18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino; and n represent 0 or 1.
Claim 16
Dependent Claim
22 words
An electrophotographic photosensitive member according to claim 14, wherein R 11 and R 12 are radicals selected from alkoxy and substituted amino.
Claim 17
Dependent Claim
18 words
An electrophotographic photosensitive member according to claim 15, wherein R 11 and R 12 are each substituted amino.
Claim 18
Dependent Claim
24 words
An electrophotographic photosensitive member according to claim 16, wherein R 11 and R 12 are radicals selected from N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-dibutylamino, and N,N-dibenzylamino.
Claim 19
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 17, wherein R 11 and R 12 are each diethylamino.
Claim 20
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 15, wherein R 11 and R 12 are each ethoxy.
Claim 21
Dependent Claim
24 words
An electrophotographic photosensitive member according to claim 14, wherein R 15 , R 16 , R 17 , and R 18 are each hydrogen.
Claim 22
Dependent Claim
12 words
An electrophotographic photosensitive member according to claim 20, wherein n is 0.
Claim 23
Dependent Claim
12 words
An electrophotographic photosensitive member according to claim 20, wherein n is 1.
Claim 24
Dependent Claim
20 words
An electrophotographic photosensitive member according to claim 20, wherein at least one of R 13 and R 14 is phenyl.
Claim 25
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 23, wherein R 13 and R 14 are each phenyl.
Claim 26
Dependent Claim
15 words
An electrophotographic photosensitive member according to claim 23, wherein R 13 is methyl or naphthyl.
Claim 27
Dependent Claim
26 words
An electrophotographic photosensitive member according to claim 14, wherein R 13 and R 14 , together with the nitrogen atom which links them, represent carbazole ring.
Claim 28
Dependent Claim
28 words
An electrophotographic photosensitive member according to claim 1, wherein said hydrazone compound is represented by formula [II] of which R is a substituted or unsubstituted divalent hydrocarbon radical.
Claim 29
Dependent Claim
22 words
An electrophotographic photosensitive member according to claim 27, wherein R is a divalent hydrocarbon radical selected from the group consisting of ##STR34##
Claim 30
Dependent Claim
15 words
An electrophotographic photosensitive member according to claim 27, wherein R is substituted or unsubstituted arylene.
Claim 31
Dependent Claim
18 words
An electrophotographic photosensitive member according to claim 29, wherein R is a divalent hydrocarbon radical selected from ##STR35##
Claim 32
Dependent Claim
28 words
An electrophotographic photosensitive member according to claim 27, wherein R 21 and R 22 are radicals selected from the group consisting of methyl, ethyl, propyl, butyl, and benzyl.
Claim 33
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 31, wherein R 21 and R 22 are each ethyl.
Claim 34
Dependent Claim
38 words
An electrophotographic photosensitive member according to claim 27, wherein R 21 and R 22 , together with the nitrogen atom which links them, represent a ring selected from the group consisting of piperidine ring, morpholine, and pyrrolidine ring.
Claim 35
Dependent Claim
20 words
An electrophotographic photosensitive member according to claim 27, wherein at least one of R 23 and R 24 is phenyl.
Claim 36
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 34, wherein R 23 and R 24 are each phenyl.
Claim 37
Dependent Claim
13 words
An electrophotographic photosensitive member according to claim 34, wherein R 23 is methyl.
Claim 38
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 27, wherein R 25 and R 26 are each hydrogen.
Claim 39
Dependent Claim
35 words
An electrophotographic photosensitive member according to claim 1, wherein a layer containing at least one hydrazone compound represented by formula [I] or [II] has a function to transport charge generated in a charge generation layer.
Claim 40
Dependent Claim
13 words
An electrophotographic photosensitive member according to claim 38, wherein said charge comprises holes.
Claim 41
Dependent Claim
32 words
An electrophotographic photosensitive member according to claim 38, wherein the layer containing at least one hydrazone compound represented by formula [I] or [II] is provided in contiguity with said charge generation layer.
Claim 42
Dependent Claim
30 words
An electrophotographic photosensitive member according to claim 40, wherein the layer containing at least one hydrazone compound represented by formula [I] or [II] is laid on said charge generation layer.
Claim 43
Dependent Claim
53 words
An electrophotographic photosensitive member according to claim 38, wherein said charge generation layer contains a compound selected from the group consisting of disazo pigments, trisazo pigments, pyrylium dyes, thiopyrylium dyes, triarylmethane dyes, thiazine dyes, cyanine dyes, phthalocyanine dyes, perylene pigments, indigo dyes, thioindigo dyes, quinacridone pigments, squaric acid pigments, and polycyclic quinone pigments.
Claim 44
Dependent Claim
20 words
An electrophotographic photosensitive member according to claim 42, wherein said charge generation layer comprises a disazo pigment and a binder.
Claim 45
Dependent Claim
15 words
An electrophotographic photosensitive member according to claim 42, wherein said phthalocyanine dye is copper phthalocyanine.
Claim 46
Dependent Claim
19 words
An electrophotographic photosensitive member according to claim 38, wherein said charge generation layer comprises an amorphous silicon base film.
Claim 47
Dependent Claim
21 words
An electrophotographic photosensitive member according to claim 45, wherein said amorphous silicon base film is a deposit formed by glow discharge.
Claim 48
Dependent Claim
21 words
An electrophotographic photosensitive member according to claim 38, wherein said charge generation layer comprises a vacuum deposition film of perylene pigment.
Claim 49
Dependent Claim
33 words
An electrophotographic photosensitive member according to claim 1, wherein the layer containing at least one hydrazone compound represented by formula [I] or [II] contains a co-crystalline complex of thiapyrylium dye and polycarbonate resin.
Claim 50
Dependent Claim
27 words
An electrophotographic photosensitive member according to claim 1, wherein the layer containing at least one hydrazone compound represented by formula [I] or [II] contains a charge-generating material.
Claim 51
Dependent Claim
275 words
An electrophotographic photosensitive member characterized by having a conductive support, a charge generation layer and a charge transport layer to transport the charge generated in said charge generation layer, said charge transport layer containing at least one hydrazone compound represented by the following formula [I] or [II]: ##STR36## wherein R 11 and R 12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R 11 and R 12 is substituted amino or alkoxy; R 13 and R 14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R 13 and R 14 is substituted or unsubstituted aryl, or R 13 and R 14 , together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; R 15 , R 16 , R 17 , and R 18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino; m and n represent 0 or 1; R 21 and R 22 , represent substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 23 and R 24 represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or R 23 and R 24 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 25 and R 26 represent hydrogen, halogen, nitro, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted acyl, or substituted or unsubstituted amino; and R represents divalent organic residue.
Claim 52
Dependent Claim
275 words
An electrophotographic photosensitive member characterized by having a conductive support, a charge generation layer and a charge transport layer to transport the charge generated in said charge generation layer, said charge transport layer containing at least one hydrazone compound represented by the following formula [I] or [II]: ##STR36## wherein R 11 and R 12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R 11 and R 12 is substituted amino or alkoxy; R 13 and R 14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R 13 and R 14 is substituted or unsubstituted aryl, or R 13 and R 14 , together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; R 15 , R 16 , R 17 , and R 18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino; m and n represent 0 or 1; R 21 and R 22 , represent substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 23 and R 24 represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or R 23 and R 24 , together with the nitrogen atom which links them, represent a five- or six-membered ring; R 25 and R 26 represent hydrogen, halogen, nitro, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted acyl, or substituted or unsubstituted amino; and R represents divalent organic residue.
Claim 53
Dependent Claim
23 words
The electrophotographic photosensitive member according to claim 50 wherein an intermediate layer is spaced between said conductive support and said charge generation layer.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-08-15 | 1987-02-14 | 1987-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-15 | 1991-02-14 | 1991-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-15 | 1995-02-14 | 1995-08-16 | $7700.00 | Window Closed / Lapsed |