US4552822A
Expired / Lapsed
US
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Photoconductive devices with hydroxy containing squaraine compositions
Assignee: Xerox Corp
•
Filing: 1983-12-05
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Granted: 1985-11-12
•
Expires: 2003-12-05
Abstract
Abstract Photoresponsive devices, including layered photoresponsive devices comprised of a photoconductive layer of squaraine compositions of the following formula: ##STR1## wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of alkyl substitutents and aryl substituents.
Inventors
- 👤 Peter M. Kazmaier
- 👤 Guiseppa Baranyi
- 👤 Cheng-Kuo Hsiao
- 👤 Richard A. Burt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 09:39
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0609; G03G5/0611; G03G5/0618
Claims Analysis
Total Claims: 72
Claim 1
Independent Claim
57 words
An improved photoresponsive device comprised in the order stated of (1) a supporting substrate, (2) a photoconductive layer comprised of the squaraine compositions of the following formula, and (3) a diamine hole transport layer ##STR4## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 2
Dependent Claim
57 words
An improved photoresponsive device comprised in the order stated of (1) a supporting substrate, (2) a photoconductive layer comprised of the squaraine compositions of the following formula, and (3) a diamine hole transport layer ##STR4## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 3
Dependent Claim
57 words
An improved photoresponsive device comprised in the order stated of (1) a supporting substrate, (2) a diamine hole transport layer, and (3) a photoconductive layer comprised of the squaraine compositions of the following formula ##STR5## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 4
Dependent Claim
57 words
An improved photoresponsive device comprised in the order stated of (1) a supporting substrate, (2) a diamine hole transport layer, and (3) a photoconductive layer comprised of the squaraine compositions of the following formula ##STR5## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 5
Dependent Claim
15 words
An improved photoresponsive device in accordance with claim 1 wherein the squaraine composition is bis(4-dimethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 6
Dependent Claim
15 words
An improved photoresponsive device in accordance with claim 2 wherein the squaraine composition is bis(4-dimethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 7
Dependent Claim
31 words
A photoresponsive device in accordance with claim 1 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition containing on its surface a semiconductive layer.
Claim 8
Dependent Claim
31 words
A photoconductive device in accordance with claim 2 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition containing on its surface a semiconductive layer.
Claim 9
Dependent Claim
24 words
A photoresponsive device in accordance with claim 5 wherein the substrate is aluminum, and a semiconductive material is transmissive aluminum or indium tin oxide.
Claim 10
Dependent Claim
25 words
A photoresponsive device in accordance with claim 6 wherein the conductive substrate is aluminum, and the semiconductive material is transmissive aluminum or indium tin oxide.
Claim 11
Dependent Claim
63 words
An improved photoresponsive device in accordance with claim 1 wherein the squaraine composition is dispersed in a resinous binder in an amount of from about 5 percent by volume to about 95 percent by volume, and the diamine hole transport material is dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight.
Claim 12
Dependent Claim
63 words
An improved photoresponsive device in accordance with claim 2 wherein the squaraine composition is dispersed in a resinous binder in an amount of from about 5 percent by volume to about 95 percent by volume, and the diamine hole transport material is dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight.
Claim 13
Dependent Claim
47 words
An improved photoresponsive device in accordance with claim 9 wherein the resinous binder for the squaraine composition is a polyester, polyvinylcarbazole, polyvinylbutyral, a polycarbonate, or a phenoxy resin, and the resinous binder for the diamine hole transport material is a polycarbonate, a polyester, or a vinyl polymer.
Claim 14
Dependent Claim
44 words
A photoresponsive device in accordance with claim 10 wherein the resinous binder for the squaraine composition is a polyester, polyvinylcarbazole, polyvinylbutyral, polycarbonate, or a phenoxy resin, and the resinous binder for the diamine hole transport material is a polycarbonate, a polyester, or vinyl polymer.
Claim 15
Dependent Claim
49 words
A photoresponsive device in accordance with claim 1 wherein the diamine composition comprises molecules of the formula: ##STR6## dispersed in a highly insulating and transparent organic resinous material wherein X is selected from the group consisting of ortho(CH 3 ), meta(CH 3 ), para(CH 3 ), ortho(Cl), meta(Cl), para(Cl).
Claim 16
Dependent Claim
49 words
A photoresponsive device in accordance with claim 2 wherein the diamine composition comprises molecules of the formula: ##STR7## dispersed in a highly insulating and transparent organic resinous material wherein X is selected from the group consisting of ortho(CH 3 ), meta(CH 3 ), para(CH 3 ), ortho(Cl), meta(Cl), para(Cl).
Claim 17
Dependent Claim
15 words
A photoresponsive device in accordance with claim 13 wherein the diamine is comprised of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 18
Dependent Claim
15 words
A photoresponsive device in accordance with claim 14 wherein the diamine is comprised of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 19
Dependent Claim
72 words
An improved photoresponsive device comprised in the order stated of the following layers, (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) an inorganic photogenerating layer, (4) a photoconductive material comprised of the squaraine compositions of the following formula, and (5) a diamine hole transport layer ##STR8## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 20
Dependent Claim
72 words
An improved photoresponsive device comprised in the order stated of the following layers, (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) an inorganic photogenerating layer, (4) a photoconductive material comprised of the squaraine compositions of the following formula, and (5) a diamine hole transport layer ##STR8## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 21
Dependent Claim
72 words
An improved photoresponsive device comprised in the order stated of the following layers, (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) a photoconductive material comprised of the squaraine compositions of the following formula, (4) an inorganic photogenerating layer, and (5) a diamine hole transport layer ##STR9## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 22
Dependent Claim
72 words
An improved photoresponsive device comprised in the order stated of the following layers, (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) a photoconductive material comprised of the squaraine compositions of the following formula, (4) an inorganic photogenerating layer, and (5) a diamine hole transport layer ##STR9## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 23
Dependent Claim
32 words
An improved photoresponsive device in accordance with claim 17 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition containing on its surface a semiconductive material.
Claim 24
Dependent Claim
31 words
A photoresponsive device in accordance with claim 18 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition containing on its surface a semiconductive material.
Claim 25
Dependent Claim
25 words
A photoresponsive device in accordance with claim 19 wherein the conductive substrate is aluminum, and the semiconductive material is transmissive aluminum, or indium tin oxide.
Claim 26
Dependent Claim
25 words
A photoresponsive device in accordance with claim 20 wherein the conductive substrate is aluminum, and the semiconductive material is transmissive aluminum, or indium tin oxide.
Claim 27
Dependent Claim
63 words
An improved photoresponsive device in accordance with claim 17 wherein the squaraine composition is dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight and the diamine hole transport material is dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight.
Claim 28
Dependent Claim
63 words
An improved photoresponsive device in accordance with claim 18 wherein the squaraine composition is dispersed in a resinous binder in an amount of from about 5 percent by volume to about 95 percent by volume, and the diamine hole transport material is dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight.
Claim 29
Dependent Claim
47 words
An improved photoresponsive device in accordance with claim 23 wherein the resinous binder for the squaraine composition is a polyester, polyvinylcarbazole, polyvinylbutyral, a polycarbonate, or a phenoxy resin, and the resinous binder for the diamine hole transport material is a polycarbonate, a polyester, or a vinyl polymer.
Claim 30
Dependent Claim
47 words
An improved photoresponsive device in accordance with claim 24 wherein the resinous binder for the squaraine composition is a polyester, polyvinylcarbazole, polyvinylbutyral, a polycarbonate, or a phenoxy resin, and the resinous binder for the diamine hole transport material is a polycarbonate, a polyester, or a vinyl polymer.
Claim 31
Dependent Claim
56 words
An improved photoresponsive device in accordance with claim 17 wherein the diamine composition comprises molecules of the formula: ##STR10## dispersed in a highly insulating and transparent organic resinous material wherein X is selected from the group consisting of ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), meta (Cl), para (Cl).
Claim 32
Dependent Claim
56 words
An improved photoresponsive device in accordance with claim 18 wherein the diamine composition comprises molecules of the formula: ##STR11## dispersed in a highly insulating and transparent organic resinous material wherein X is selected from the group consisting of ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), meta (Cl), para (Cl).
Claim 33
Dependent Claim
28 words
An improved photoresponsive device in accordance with claim 27 wherein the resinous binder for the diamine hole transport material is a polycarbonate, a polyester, or a vinyl polymer.
Claim 34
Dependent Claim
28 words
An improved photoresponsive device in accordance with claim 28 wherein the resinous binder for the diamine hole transport material is a polycarbonate, a polyester, or a vinyl polymer.
Claim 35
Dependent Claim
16 words
An improved photoresponsive device in accordance with claim 27 wherein the diamine is comprised of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 36
Dependent Claim
16 words
An improved photoresponsive device in accordance with claim 28 wherein the diamine is comprised of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 37
Dependent Claim
27 words
An improved photoresponsive device in accordance with claim 17 wherein the photogenerating layer is selenium, a halogen doped selenium substance, selenium alloys, or halogen doped selenium alloys.
Claim 38
Dependent Claim
27 words
An improved photoresponsive device in accordance with claim 18 wherein the photogenerating layer is selenium, a halogen doped selenium substance, selenium alloys, or halogen doped selenium alloys.
Claim 39
Dependent Claim
22 words
An improved photoresponsive device in accordance with claim 33 wherein the selenium alloy is selenium tellurium, selenium arsenic, or selenium tellurium arsenic.
Claim 40
Dependent Claim
22 words
An improved photoresponsive device in accordance with claim 33 wherein the selenium alloy is selenium tellurium, selenium arsenic, or selenium tellurium arsenic.
Claim 41
Dependent Claim
33 words
An improved photoresponsive device in accordance with claim 35 wherein the selenium alloy is doped with chlorine in an amount of from about 50 parts per million to about 200 parts per million.
Claim 42
Dependent Claim
33 words
An improved photoresponsive device in accordance with claim 36 wherein the selenium alloy is doped with chlorine in an amount of from about 50 parts per million to about 200 parts per million.
Claim 43
Dependent Claim
16 words
An improved photoresponsive device in accordance with claim 17 wherein the photogenerating layer is trigonal selenium.
Claim 44
Dependent Claim
16 words
An improved photoresponsive device in accordance with claim 18 wherein the photogenerating layer is trigonal selenium.
Claim 45
Dependent Claim
28 words
An improved photoresponsive device in accordance with claim 17 wherein the photogenerating layer is trigonal selenium doped with Na 2 SeO 3 and Na 2 CO 3 .
Claim 46
Dependent Claim
14 words
A photoresponsive device in accordance with claim 17 wherein the squaraine composition is bis(4-dimethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 47
Dependent Claim
14 words
A photoresponsive device in accordance with claim 18 wherein the squaraine composition is bis(4-dimethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 48
Dependent Claim
4 words
The squaraine composition bis(4-ethylmethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 49
Dependent Claim
4 words
The squaraine composition bis(4-ethylmethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 50
Dependent Claim
4 words
The squaraine composition bis(4-dimethylamino-2-ethyl-6-hydroxyphenyl)squaraine.
Claim 51
Dependent Claim
4 words
The squaraine composition bis(4-dimethylamino-2-ethyl-6-hydroxyphenyl)squaraine.
Claim 52
Dependent Claim
53 words
An improved photoresponsive imaging member consisting essentially of a supporting substrate, a photoconductive layer comprised of a squaraine compound of the following formula ##STR12## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents; and an aryl amine hole transport layer.
Claim 53
Dependent Claim
53 words
An improved photoresponsive imaging member consisting essentially of a supporting substrate, a photoconductive layer comprised of a squaraine compound of the following formula ##STR12## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents; and an aryl amine hole transport layer.
Claim 54
Dependent Claim
24 words
An improved photoresponsive imaging member in accordance with claim 46 wherein the squaraine is selected from the group consisting of bis(4-dimethylamino-2-hydroxy-6-methylphenyl)squaraine; bis(4-dibutylamino-2-hydroxy-6-methylphenyl)squaraine; and bis(4-diethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 55
Dependent Claim
14 words
An imaging member in accordance with claim 46 wherein the aryl amine is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 56
Dependent Claim
27 words
An improved photoresponsive device in accordance with claim 17 further including an adhesive layer situated between the metal oxide hole blocking layer in the inorganic photogenerating layer.
Claim 57
Dependent Claim
31 words
An improved photoresponsive device in accordance with claim 18 wherein there is further included an adhesive layer situated between the metal oxide hole blocking layer and the photoconductive squaraine composition layer.
Claim 58
Dependent Claim
30 words
Squaraine compositions of the following formula: ##STR13## wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 59
Dependent Claim
30 words
Squaraine compositions of the following formula: ##STR13## wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of alkyl substituents and aryl substituents.
Claim 60
Dependent Claim
23 words
A squaraine composition in accordance with claim 51 wherein the alkyl substituents contain from about 1 carbon atom to about 20 carbon atoms.
Claim 61
Dependent Claim
19 words
A squaraine composition in accordance with claim 52 wherein the alkyl substituents are methyl, ethyl, propyl, butyl, or pentyl.
Claim 62
Dependent Claim
21 words
A squaraine composition in accordance with claim 51 wherein the aryl substituent contains from about 6 to about 24 carbon atoms.
Claim 63
Dependent Claim
14 words
A squaraine composition in accordance with claim 54 wherein the aryl substituent is phenyl.
Claim 64
Dependent Claim
31 words
A squaraine composition in accordance with claim 51 wherein R 1 , R 2 , and R 3 , are alkyl substituents of from about 1 to about 10 carbon atoms.
Claim 65
Dependent Claim
14 words
A squaraine composition in accordance with claim 56 wherein the alkyl substituent is methyl.
Claim 66
Dependent Claim
14 words
A squaraine composition in accordance with claim 56 wherein the alkyl substituents are methyl.
Claim 67
Dependent Claim
4 words
The squaraine composition bis(4-dimethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 68
Dependent Claim
4 words
The squaraine composition bis(4-dimethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 69
Dependent Claim
4 words
The squaraine composition bis(4-dibutylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 70
Dependent Claim
4 words
The squaraine composition bis(4-dibutylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 71
Dependent Claim
4 words
The squaraine composition bis(4-diethylamino-2-hydroxy-6-methylphenyl)squaraine.
Claim 72
Dependent Claim
4 words
The squaraine composition bis(4-diethylamino-2-hydroxy-6-methylphenyl)squaraine.
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) | 1988-11-11 | 1989-05-13 | 1989-11-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-11-11 | 1993-05-13 | 1993-11-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-11-11 | 1997-05-13 | 1997-11-12 | $7700.00 | Window Closed / Lapsed |