US4487824A
Expired / Lapsed
US
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Electrophotographic photosensitive member containing a halogen substituted hydrazone
Assignee: Canon Inc
•
Filing: 1983-05-09
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Granted: 1984-12-11
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Expires: 2003-05-09
Abstract
Abstract An electrophotographic photosensitive member comprises an electrically conductive substrate and a layer containing a hydrazone compound represented by the following formula (1) and a binder: ##STR1## wherein; R 1 and R 2 each represent alkyl, aralkyl, or aryl, substituted or unsubstituted, or R 1 and R 2 together with the nitrogen atom to which they are attached form a 5- or 6-membered ring; R 3 represents halogen or fluoroalkyl; R 4 and R 6 each represent hydrogen or halogen; R 5 represents hydrogen, alkyl, alkoxyl, or halogen; each of R 7 and R 8 represents alkyl, aralkyl, or aryl, substituted or unsubstituted; and n represents an integer of 0 or 1.
Inventors
- 👤 Kazuharu Katagiri
- 👤 Katsunori Watanabe
- 👤 Kiyoshi Sakai
- 👤 Shozo Ishikawa
- 👤 Makoto Kitahara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 05:09
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/12; C07D295/135; C07C; C07C251/00; C07C251/72; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0612; G03G5/0616; G03G5/0618; G03G5/0664; G03G5/0666; G03G5/0668
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
111 words
An electrophotographic photosensitive member comprising an electrically conductive substrate and a layer comprising a hydrazone compound represented by the following formula (1) and a binder: ##STR7## wherein; R 1 and R 2 each represent alkyl, aralkyl, or aryl, substituted or unsubstituted, or R 1 and R 2 together with the nitrogen atom to which they are attached form a 5- or 6-membered ring; R 3 represents halogen or fluoroalkyl; R 4 and R 6 each represent hydrogen or halogen; R 5 represents hydrogen, alkyl, alkoxy, or halogen; each of R 7 and R 8 represents alkyl, aralkyl, or aryl, substituted or unsubstituted; and n represents an integer of 0 or 1.
Claim 2
Dependent Claim
111 words
An electrophotographic photosensitive member comprising an electrically conductive substrate and a layer comprising a hydrazone compound represented by the following formula (1) and a binder: ##STR7## wherein; R 1 and R 2 each represent alkyl, aralkyl, or aryl, substituted or unsubstituted, or R 1 and R 2 together with the nitrogen atom to which they are attached form a 5- or 6-membered ring; R 3 represents halogen or fluoroalkyl; R 4 and R 6 each represent hydrogen or halogen; R 5 represents hydrogen, alkyl, alkoxy, or halogen; each of R 7 and R 8 represents alkyl, aralkyl, or aryl, substituted or unsubstituted; and n represents an integer of 0 or 1.
Claim 3
Dependent Claim
41 words
The electrophotographic photosensitive member of claim 1, which comprises two photosensitive layers, one being a charge generation layer and the other being a charge transport layer which is said layer containing a hydrazone compound of the formula (1) and a binder.
Claim 4
Dependent Claim
82 words
The electrophotographic photosensitive member of claim 2, wherein said charge generation layer comprises at least one photoconductive material selected from the group consisting of selenium, selenium-tellulium, pyrylium series dyes, co-crystalline complexes of pyrylium series dyes, thiopyrylium series dyes, co-crystalline complexes of thiopyrylium series dyes, phthalocyanine series pigments, anthoanthrone pigments, dibenzpyrenequinone pigments, pyranethrone pigments, trisazo pigments, disazo pigments, monoazo pigments, indigo dyes, quinacridone series pigments, asymmetric quinocyanine dyes, quinocyanine dyes, amorphous silicon, squaric acid type dyes, thioindigo series dyes, and perylene series pigments.
Claim 5
Dependent Claim
35 words
The electrophotographic photosensitive member of claim 3, wherein said charge generation layer comprises at least one photoconductive material selected from the group consisting of selenium, selenium-tellulium, phthalocyanine series pigments, amorphous silicon, and perylene series pigments.
Claim 6
Dependent Claim
17 words
The electrophotographic photosensitive member of claim 4, wherein said charge generation layer is an amorphous silicon film.
Claim 7
Dependent Claim
78 words
The electrophotographic photosensitive member of claim 3, wherein said charge generation layer comprises a binder and at least one photocondcutive material selected from the group consisting of pyrylium series dyes, co-crystalline complexes of pyrylium series dyes, thiopyrylium series dyes, co-crystalline complexes of thiopyrylium series dyes, phthalocyanine series pigments, anthoanthrone pigments, dibenzpyrenequinone pigments, pyranethrone pigments, trisazo pigments, disazo pigments, monoazo pigments, indigo dyes, quinacridone series pigments, asymmetric quinocyanine dyes, quinocyanine dyes, squaric acid type dyes, and thioindigo series dyes.
Claim 8
Dependent Claim
20 words
The electrophotographic photosensitive member of claim 6, wherein said charge generation layer comprises a phothalocyanine series pigment and a binder.
Claim 9
Dependent Claim
15 words
The electrophotographic photosensitive member of claim 7, wherein said phthalocyanine series dye is copper phthalocyanine.
Claim 10
Dependent Claim
19 words
The electrophotographic photosensitive member of claim 6, wherein said charge generation layer comprises a disazo pigment and a binder.
Claim 11
Dependent Claim
30 words
The electrophotographic photosensitive member of claim 6, wherein said charge generation layer comprises a binder and either a pyrylium series dye or a co-crystalline complex of a pyrylium series dye.
Claim 12
Dependent Claim
30 words
The electrophotographic photosensitive member of claim 6, wherein said charge generation layer comprises a binder and either a thiopyrylium series dye or a co-crystalline complex of a thiopyrylium series dye.
Claim 13
Dependent Claim
28 words
The electrophotographic photosensitive member of claim 1, wherein said layer comprising a hydrazone compound of the formula (1) and a binder contains further a photoconductive pigment or dye.
Claim 14
Dependent Claim
73 words
The electrophotographic photosensitive member of claim 12, wherein said photoconductive pigment or dye is a compound selected from the group consisting of pyrylium series dyes, co-crystalline complexes of pyrylium series dye, thiopyrylium series dyes, co-crystalline complexes of thiopyrylium series dye, phthalocyanine series pigments, anthoanthrone dyes, dibenzpyrenequinone pigments, pyranethrone pigments, trisazo pigments, disazo pigments, monoazo pigments, indigo dyes, quinacridone series pigments, asymmetric quinocyanine dyes, quinocyanine dyes, squaric acid type dyes, and thioindigo series dyes.
Claim 15
Dependent Claim
23 words
The electrophotographic photosensitive member of claim 2, wherein said charge transport layer is laid on the upper side of the charge generation layer.
Claim 16
Dependent Claim
23 words
The electrophotographic photosensitive member of claim 2, wherein said charge transport layer is laid on the lower side of the charge generation layer.
Claim 17
Dependent Claim
31 words
The electrophotographic photosensitive member of claim 1, which has an intermediate layer between the electrically conductive substrate and the layer containing a hydrazone compound of the formula (1) and a binder.
Claim 18
Dependent Claim
46 words
The electrophotographic photosensitive member of claim 16, which as the intermediate layer between the electrically conductive substrate and a photosensitive layer comprising a charge generation layer and a charge transport layer which is said layer containing a hydrazone compound of the formula (1) and a binder.
Claim 19
Dependent Claim
16 words
The electrophotographic photosensitive member of claim 16, wherein said intermediate layer is an under coating layer.
Claim 20
Dependent Claim
26 words
The electrophotographic photosensitive member of claim 1, wherein R 1 and R 2 in the formula (1) are each methyl, ethyl, propyl, butyl, benzyl, or phenyl.
Claim 21
Dependent Claim
15 words
The electrophotographic photosensitive member of claim 1, wherein n in the fomula (1) is zero.
Claim 22
Dependent Claim
20 words
The electrophotographic photosensitive member of claim 1, wherein R 3 in the formula (1) is chlorine, bromine, iodine or trifluoromethyl.
Claim 23
Dependent Claim
20 words
The electrophotographic photosensitive member of claim 1, wherein R 4 and R 6 are each hydrogen, chlorine, bromine, or iodine.
Claim 24
Dependent Claim
29 words
The electrophotographic photosensitice member of claim 1, wherein R 5 in the formula (1) is hydrogen, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, fluorine, chlorine, bromine, or iodine.
Claim 25
Dependent Claim
30 words
The electrophotographic photosensitive member of claim 1, wherein R 7 and R 8 in the formula (1) are each methyl, ethyl, propyl, butyl, benzyl, phenethyl, naphthylmethyl, phenyl, naphthyl, or anthryl.
Claim 26
Dependent Claim
32 words
The electrophotographic photosensitive member of claim 1, wherein R 1 and R 2 in the formula (1) together with the nitrogen atom to which they are attached form pyrrolidinyl, piperidino, or morphlino.
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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) | 1987-12-11 | 1988-06-11 | 1988-12-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-11 | 1992-06-11 | 1992-12-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-11 | 1996-06-11 | 1996-12-11 | $7700.00 | Window Closed / Lapsed |