US4621038A
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Photoconductive imaging members with novel symmetrical fluorinated squaraine compounds
Assignee: Xerox Corp
•
Filing: 1985-06-24
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Granted: 1986-11-04
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Expires: 2005-06-24
Abstract
Abstract Disclosed are fluorinated squaraine compounds of the following formula: ##STR1## wherein R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl, aryl, and heterocyclic substituents.
Inventors
- 👤 Peter M. Kazmaier
- 👤 Giuseppa Baranyi
- 👤 Rafik O. Loutfy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:52
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0618; G03G5/0609; G03G5/0611
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
58 words
An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a photoconductive layer comprised of symmetrical fluorinated squaraine compounds of the following formula ##STR5## wherein the R 1 , R 2 and R 3 substituents are independently selected from the group consisting of alkyl, aryl, and heterocyclic substituents, and (3) an aryl diamine hole transport layer.
Claim 2
Dependent Claim
58 words
An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a photoconductive layer comprised of symmetrical fluorinated squaraine compounds of the following formula ##STR5## wherein the R 1 , R 2 and R 3 substituents are independently selected from the group consisting of alkyl, aryl, and heterocyclic substituents, and (3) an aryl diamine hole transport layer.
Claim 3
Dependent Claim
25 words
An improved photoresponsive imaging member in accordance with claim 1 wherein the supporting substrate is comprised of a conductive material or an organic polymeric composition.
Claim 4
Dependent Claim
16 words
An improved photoresponsive imaging member in accordance with claim 1 wherein the fluorinated squaraine is bis(4-dimethylamine-2-fluoro-6-methylphenyl).
Claim 5
Dependent Claim
62 words
An improved photoresponsive imaging member in accordance with claim 1 wherein the fluorinated squaraine is dispersed in a resinous binder in an amount of from about 5 percent to about 95 percent by volume, and the diamine hole transport molecules are dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight.
Claim 6
Dependent Claim
46 words
An improved photoresponsive imaging member in accordance with claim 4 wherein the resinous binder for the squaraine compound is a polyester, polyvinylbutyral polyvinylcarbazole, or a phenoxy resin; and the resinous binder for the diamine hole transport material is a polycarbonate, a polyester, or a vinyl polymer.
Claim 7
Dependent Claim
42 words
An improved photoresponsive imaging member in accordance with claim 1 wherein the diamine composition comprises molecules of the formula: ##STR6## dispersed in a highly insulating and transparent organic resinous binder, wherein X is selected from the group consisting of alkyl and halogen.
Claim 8
Dependent Claim
32 words
An improved photoresponsive imaging member in accordance with claim 6 wherein X is ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), meta (Cl), or para (Cl).
Claim 9
Dependent Claim
15 words
An improved photoresponsive imaging member in accordance with claim 6 wherein the diamine is N,N'-diphenyl-N,N'-bis(3-methylphenyl)[1,1-biphenyl]-4,4'-diamine.
Claim 10
Dependent Claim
29 words
An improved photoresponsive imaging member in accordance with claim 6 wherein the fluorinated squaraine photogenerating layer is situated between the supporting substrate, and the aryl diamine hole transport layer.
Claim 11
Dependent Claim
28 words
An improved photoresponsive imaging member in accordance with claim 6 wherein the aryl diamine hole transport layer is situated between the squaraine photogenerating layer, and the supporting substrate.
Claim 12
Dependent Claim
70 words
An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) an inorganic photogenerating layer, (4) a photoconductive layer comprised of symmetrical fluorinated squaraine compounds of the following formula ##STR7## wherein the R 1 , R 2 and R 3 substituents are independently selected from the group consisting of alkyl, aryl, and hetrocyclic substituents, and (5) an aryl diamine hole transport layer.
Claim 13
Dependent Claim
70 words
An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) an inorganic photogenerating layer, (4) a photoconductive layer comprised of symmetrical fluorinated squaraine compounds of the following formula ##STR7## wherein the R 1 , R 2 and R 3 substituents are independently selected from the group consisting of alkyl, aryl, and hetrocyclic substituents, and (5) an aryl diamine hole transport layer.
Claim 14
Dependent Claim
70 words
An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) a photoconductive layer comprised of symmetrical fluorinated squaraine compounds of the following formula ##STR8## wherein the R 1 , R 2 and R 3 substituents are independently selected from the group consisting of alkyl, aryl, and heterocyclic substituents (4) an inorganic photogenerating layer, and (5) an aryl diamine hole transport layer.
Claim 15
Dependent Claim
70 words
An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a metal oxide hole blocking layer, (3) a photoconductive layer comprised of symmetrical fluorinated squaraine compounds of the following formula ##STR8## wherein the R 1 , R 2 and R 3 substituents are independently selected from the group consisting of alkyl, aryl, and heterocyclic substituents (4) an inorganic photogenerating layer, and (5) an aryl diamine hole transport layer.
Claim 16
Dependent Claim
17 words
An improved photoresponsive imaging member in accordance with claim 11 wherein the fluorinated squaraine compound is bis(4-dimethylamine-2-fluoro-6-methylphenyl).
Claim 17
Dependent Claim
17 words
An improved photoresponsive imaging member in accordance with claim 12 wherein the fluorinated squaraine compound is bis(4-dimethylamine-2-fluoro-6-methylphenyl).
Claim 18
Dependent Claim
26 words
An improved photoresponsive imaging member in accordance with claim 11 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition.
Claim 19
Dependent Claim
26 words
An improved photoresponsive imaging member in accordance with claim 12 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition.
Claim 20
Dependent Claim
58 words
An improved photoresponsive imaging member in accordance with claim 11 wherein the aryl diamine comprises molecules of the formula: ##STR9## 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), or para (Cl).
Claim 21
Dependent Claim
58 words
An improved photoresponsive imaging member in accordance with claim 12 wherein the aryl diamine 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), or para (Cl).
Claim 22
Dependent Claim
27 words
An improved photoresponsive imaging member in accordance with claim 17 wherein the resinous binder for the aryl diamine is a polycarbonate, a polyester, or a vinyl polymer.
Claim 23
Dependent Claim
27 words
An improved photoresponsive imaging member in accordance with claim 18 wherein the resinous binder for the aryl diamine is a polycarbonate, a polyester, or a vinyl polymer.
Claim 24
Dependent Claim
16 words
An improved photoresponsive imaging member in accordance with claim 17 wherein the aryl diamine is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 25
Dependent Claim
16 words
An improved photoresponsive imaging member in accordance with claim 18 wherein the aryl diamine is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 26
Dependent Claim
38 words
An improved photoreceptive imaging member in accordance with claim 11 wherein the photogenerating layer is comprised of a component selected from the group consisting of selenium, a halogen doped selenium substance, selenium alloys, and halogen doped selenium alloys.
Claim 27
Dependent Claim
38 words
An improved photoresponsive imaging member in accordance with claim 12 wherein the photogenerating layer is comprised of a component selected from the group consisting of selenium, a halogen doped selenium substance, selenium alloys, and halogen doped selenium alloys.
Claim 28
Dependent Claim
33 words
An improved photoresponsive imaging member in accordance with claim 23 wherein the selenium alloy is comprised of a component selected from the group consisting of selenium tellurium, selenium arsenic, and selenium tellurium arsenic.
Claim 29
Dependent Claim
33 words
An improved photoresponsive imaging member in accordance with claim 24 wherein the selenium alloy is comprised of a component selected from the group consisting of selenium tellurium, selenium arsenic, and selenium tellurium arsenic.
Claim 30
Dependent Claim
17 words
An improved photoresponsive imaging member in accordance with claim 11 wherein the photogenerating layer is trigonal selenium.
Claim 31
Dependent Claim
17 words
An improved photoresponsive imaging member in accordance with claim 12 wherein the photogenerating layer is trigonal selenium.
Claim 32
Dependent Claim
31 words
An improved photoresponsive imaging member in accordance with claim 11 wherein the photogenerating layer is comprised of trigonal selenium doped with Na 2 SeO 3 and Na 2 CO 3 .
Claim 33
Dependent Claim
31 words
An improved photoresponsive imaging member in accordance with claim 12 wherein the photogenerating layer is composed of trigonal selenium doped with Na 2 SeO 3 and Na 2 CO 3 .
Claim 34
Dependent Claim
17 words
An improved photoresponsive imaging member in accordance with claim 17 wherein the adhesive layer is a silane.
Claim 35
Dependent Claim
17 words
An improved photoresponsive imaging member in accordance with claim 12 wherein the adhesive layer is a silane.
Claim 36
Dependent Claim
15 words
An improved photoresponsive imaging member in accordance with claim 1 wherein R 1 is methyl.
Claim 37
Dependent Claim
21 words
An improved photoresponsive imaging member in accordance with claim 1 wherein R 1 , R 2 and R 3 are methyl.
Claim 38
Dependent Claim
15 words
An improved photoresponsive imaging member in accordance with claim 11 wherein R 2 is methyl.
Claim 39
Dependent Claim
21 words
An improved photoresponsive imaging member in accordance with claim 12 wherein R 1 , R 2 and R 3 are methyl.
Claim 40
Dependent Claim
28 words
An improved photoresponsive imaging member in accordance with claim 11 further including an adhesive layer situated between the metal oxide hole blocking layer and the inorganic photogenerating layer.
Claim 41
Dependent Claim
27 words
An improved photoresponsive imaging member in accordance with claim 12 further including an adhesive layer situated between the metal oxide hole blocking layer and the photoconductive layer.
Claim 42
Dependent Claim
20 words
An improved photoresponsive imaging member in accordance with claim 15 wherein the substrate contains on the surface a semiconductive material.
Claim 43
Dependent Claim
20 words
An improved photoresponsive imaging member in accordance with claim 16 wherein th substrate contains on the surface a semiconductive material.
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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) | 1989-11-03 | 1990-05-05 | 1990-11-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-11-03 | 1994-05-05 | 1994-11-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-11-03 | 1998-05-05 | 1998-11-04 | $7700.00 | Window Closed / Lapsed |