Patent JPS55147461A successfully refreshed from Google Patents.
US4420548A
Expired / Lapsed
US
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Electrophotographic member with hydrazone or ketazine compounds
Assignee: Canon Inc
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Filing: 1981-11-16
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Granted: 1983-12-13
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Expires: 2001-11-16
Abstract
Abstract An electrophotographic photosensitive member is characterized by having a layer containing at least one of hydrazone group compounds represented by the following formula (1) or of ketazine group compounds represented by the following formula (2): ##STR1## In the formula, R 11 and R 12 independently of one another represent hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; R 13 and R 14 independently of one another represent subsituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; and R 15 represents a divalent organic residue. ##STR2## In the formula, R 21 , R 22 , R 23 , and R 24 independently one another represent substituted or unsubstituted alkyl, substituted or substituted aralkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen which links them, represent cyclic amino radical, and R 23 and R 24 , together with the nitrogen which links them, represent cyclic amino radical.
Inventors
- 👤 Kiyoshi Sakai
- 👤 Minoru Mabuchi
- 👤 Toshiko Suzuki
- 👤 Yuji Egarashi
- 👤 Shozo Ishikawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 18:19
CPC Classifications
C; C07; C07C; C07C251/00; C07C251/72; C07C251/88; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0612; G03G5/0616; G03G5/0622; G03G5/0624; G03G5/0627; G03G5/0635; G03G5/0644; G03G5/0661
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
173 words
An electrophotographic photosensitive member characterized by having a layer containing at least one of hydrazone group compounds represented by the following formula (1) or of ketazine group compounds represented by the following formula (2): ##STR49## wherein R 11 and R 12 independently of one another are hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; R 13 and R 14 independently of one another are substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted heterocyclic radical; and R 15 ; is a divalent hydrocarbon radical which may be substituted, a divalent organic residue derived from a heterocyclic ring which may be substituted, ##STR50## ##STR51## wherein R 21 , R 22 , R 23 , and R 24 independently of one another are substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen which links them, is cyclic amino radical, and R 23 and R 24 , together with the nitrogen which links them, is cyclic amino radical.
Claim 2
Dependent Claim
173 words
An electrophotographic photosensitive member characterized by having a layer containing at least one of hydrazone group compounds represented by the following formula (1) or of ketazine group compounds represented by the following formula (2): ##STR49## wherein R 11 and R 12 independently of one another are hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; R 13 and R 14 independently of one another are substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted heterocyclic radical; and R 15 ; is a divalent hydrocarbon radical which may be substituted, a divalent organic residue derived from a heterocyclic ring which may be substituted, ##STR50## ##STR51## wherein R 21 , R 22 , R 23 , and R 24 independently of one another are substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, or R 21 and R 22 , together with the nitrogen which links them, is cyclic amino radical, and R 23 and R 24 , together with the nitrogen which links them, is cyclic amino radical.
Claim 3
Dependent Claim
30 words
An electrophotographic photosensitive member according to claim 1, wherein R 11 is a radical selected from the group consisting of p-dialkylaminophenyl, p-di-aralkylaminophenyl, p-diarylaminophenyl, p-morpholinophenyl, p-piperidinophenyl, p-pyrrolidinophenyl, p-alkoxyphenyl, p-dialkylamino-1-naphthyl, and N-alkylcarbazolyl.
Claim 4
Dependent Claim
13 words
An electrophotographic photosensitive member according to claim 2, wherein R 11 is p-dialkylaminophenyl.
Claim 5
Dependent Claim
25 words
An electrophotographic photosensitive member according to claim 3, wherein R 11 is a radical selected from the group consisting of p-dimethylaminophenyl, p-diethylaminophenyl, p-dipropylaminophenyl, and p-dibutylaminophenyl.
Claim 6
Dependent Claim
13 words
An electrophotographic photosensitive member according to claim 4, wherein R 11 is p-diethylaminophenyl.
Claim 7
Dependent Claim
15 words
An electrophotographic photosensitive member according to any of claims 2-5, wherein R 12 is hydrogen.
Claim 8
Dependent Claim
18 words
An electrophotographic photosensitive member according to any of claims 2-5, wherein R 12 is substituted or unsubstituted aryl.
Claim 9
Dependent Claim
23 words
An electrophotographic photosensitive member according to claim 7, wherein said aryl is a radical selected from the group consisting of phenyl and p-dialkylaminophenyl.
Claim 10
Dependent Claim
24 words
An electrophotographic photosensitive member according to claim 1, wherein R 15 is a radical selected from the group consisting of from alkylene and arylene.
Claim 11
Dependent Claim
25 words
An electrophotographic photosensitive member according to claim 9, wherein R 15 is a radical selected from the group consisting of methylene, ethylene, p-phenylene, and 2,7-naphthylene.
Claim 12
Dependent Claim
23 words
An electrophotographic photosensitive member according to claim 1, wherein R 15 is a divalent organic residue selected from the group consisting of ##STR52##
Claim 13
Dependent Claim
33 words
An electrophotographic photosensitive member according to claim 1, wherein R 15 is a divalent organic residue derived from a heterocyclic ring selected from the group consisting of pyridine, quinoline, carbazole, phenothiazine, and phenoxazine.
Claim 14
Dependent Claim
19 words
An electrophotographic photosensitive member according to claim 12, wherein R 15 is a divalent organic residue derived from N-ethylcarbazole.
Claim 15
Dependent Claim
47 words
An electrophotographic photosensitive member according to claim 1, wherein R 13 and R 14 are the same or different and each represents a radical selected from the group consisting of phenyl, p-dialkylaminophenyl, p-diaralkylaminophenyl, p-methoxyphenyl, naphthyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, 1,3-dimethylbutyl, benzyl, 2-pyridyl, and 2-quinolyl.
Claim 16
Dependent Claim
40 words
An electrophotographic photosensitive member according to claim 14, wherein, R 13 and R 14 are the same or different and each represents a radical selected from the group consisting of phenyl, p-dimethylaminophenyl, p-diethylaminophenyl, p-dibenzylaminophenyl, p-ethoxyphenyl, β-naphthyl, methyl, ethyl, and 1,3-dimethylbutyl.
Claim 17
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 15, wherein R 13 and R 14 are each phenyl.
Claim 18
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 15, wherein R 13 and R 14 are each p-diethylaminophenyl.
Claim 19
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 15, wherein R 13 and R 14 are each β-naphthyl.
Claim 20
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 15, wherein R 13 and R 14 are each methyl.
Claim 21
Dependent Claim
17 words
An electrophotographic photosensitive member according to claim 15, wherein R 13 and R 14 are each ethyl.
Claim 22
Dependent Claim
18 words
An electrophotographic photosensitive member according to claim 15, wherein R 13 is 1,3-dimethylbutyl and R 14 is phenyl.
Claim 23
Dependent Claim
45 words
An electrophotographic photosensitive member according to claim 1, wherein R 21 , R 22 , R 23 , and R 24 are the same or different and each represents a radical selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, benzyl, 2-dimethylaminoethyl, and 2-ethoxyethyl.
Claim 24
Dependent Claim
24 words
An electrophotographic photosensitive member according to claim 22, wherein R 21 , R 22 , R 23 , and R 24 are each ethyl.
Claim 25
Dependent Claim
51 words
An electrophotographic photosensitive member according to claim 1, wherein R 21 and R 22 , together with the nitrogen which links them, and R 23 and R 24 , together with the nitrogen which links them, form each a ring selected from the group consisting of pyrrolidine, piperidine, and morpholine rings.
Claim 26
Dependent Claim
56 words
An electrophotographic photosensitive member according to claim 24, wherein the combination of neighboring R 21 , R 22 , and the nitrogen which links R 21 and R 22 , and the combination of neighboring R 23 , R 24 , and the nitrogen which links R 23 and R 24 from each a pyrrolidine ring.
Claim 27
Dependent Claim
38 words
An electrophotographic photosensitive member according to claim 1, wherein said layer containing at least one of hydrazone group compounds or of ketazine group compounds has a function to transport the electric charge generated in a charge generation layer.
Claim 28
Dependent Claim
14 words
An electrophotographic photosensitive member according to claim 26, wherein said electric charge comprises holes.
Claim 29
Dependent Claim
33 words
An electrophotographic photosensitive member according to claim 26, wherein said layer containing at least one of hydrazone group compounds or of ketazine group compounds is laid in contiguity with the charge generation layer.
Claim 30
Dependent Claim
31 words
An electrophotographic photosensitive layer according to claim 28, wherein said layer containing at least one of hydrazone group compounds or of ketazine group compounds is laid above the charge generation layer.
Claim 31
Dependent Claim
49 words
An electrophotographic photosensitive layer according to claim 29, wherein said charge generation layer contains a compound selected from the group consisting of azo pigments, pyrylium dyes, thiopyrylium dyes, triarylmethane dyes, thiazine dyes, cyanine dyes, phthalocyanine dyes, indigo dyes, thioindigo dyes, quinacridone pigments, squaric acid pigments, and polycyclic quinone pigments.
Claim 32
Dependent Claim
20 words
An electrophotographic photosensitive member according to claim 30, wherein said charge generation layer comprises a bis-azo pigment and a binder.
Claim 33
Dependent Claim
23 words
An electrophotographic photosensitive member according to claim 30, wherein said charge generation layer comprises methine dyes derived from squaric acid and a binder.
Claim 34
Dependent Claim
20 words
An electrophotographic photosensitive member according to claim 30, wherein said charge generation layer comprises a vacuum deposition film of selenium-tellurium.
Claim 35
Dependent Claim
18 words
An electrophotographic photosensitive member according to claim 26, wherein said charge generation layer comprises an amorphous silicon film.
Claim 36
Dependent Claim
19 words
An electrophotographic photosensitive member according to claim 34, said amorphous silicon coat is a film formed by glow discharge.
Claim 37
Dependent Claim
22 words
An electrophotographic photosensitive member according to claim 26, wherein said charge generation layer comprises a vacuum deposition film of a perylene pigment.
Claim 38
Dependent Claim
19 words
An electrophotographic photosensitive member according to claim 26, wherein said charge generation layer is laid on a conductive layer.
Claim 39
Dependent Claim
23 words
An electrophotographic photosensitive member according to claim 37, wherein an intermediate layer is laid between said conductive layer and said charge generation layer.
Claim 40
Dependent Claim
33 words
An electrophotographic photosensitive member according to claim 1, wherein said layer containing at least one of hydrazone group compounds or of ketazine group compounds contains an organic photoconductive polymer and a charge-generating material.
Claim 41
Dependent Claim
14 words
An electrophotographic photosensitive member according to claim 39, wherein said photoconductive polymer is poly(N-vinylcarbazole).
Claim 42
Dependent Claim
32 words
An electrophotographic photosensitive member according to claim 39, which comprises at least one of said hydrazone group compounds or of said ketazine group compounds, a charge-generating material, and an organic photoconductive polymer.
Claim 43
Dependent Claim
14 words
An electrophotographic photosensitive member according to claim 41, wherein said photoconductive polymer is poly(N-vinylcarbazole).
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-12-12 | 1987-06-13 | 1987-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-12 | 1991-06-13 | 1991-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-12 | 1995-06-13 | 1995-12-13 | $7700.00 | Window Closed / Lapsed |