US4795242A
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Conducting substituted polyisothianaphthenes
Assignee: University of California, San Diego
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Filing: 1986-12-18
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Granted: 1989-01-03
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Expires: 2006-12-18
Abstract
Abstract Polyisothianaphthene substituted in the 5 and/or 6 positions so as to have an oxygen atom adjacent to C 5 or C 6 . Substituents include alkoxys, hydroxys and dioxyalkylenes. The polymers are conducting and useful in electrochromic displays and as electrode materials.
Inventors
- 👤 Wudl: Fred
- 👤 Alan Heeger
- 👤 Yoshiaki Ikenoue
- 👤 Masao Kobayashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:40
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/12; C08G61/122; C08G61/123; C09; C09K; C09K9/00; C09K9/02; G; G02; G02F; G02F1/00; G02F1/01; G02F1/15; G02F1/1514; G02F1/1516; G02F1/15165; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/127; H01M; H01M4/00; H01M4/02; H01M4/36; H01M4/60; Y; Y02; Y02E; Y02E60/00; Y02E60/10
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
151 words
A polymer having a structural formula selected from the group consisting of Ia and Ib wherein: ##STR16## R 1 is hydrogen or --OR 3 ; R 2 and R 3 are selected independently from the group consisting of hydrogen and C 1 to C 8 hydrocarbons, with the proviso that R 2 and R 3 may be linked together to form, with both oxygens, a dioxyalkylene substituent on the benzene ring with the formula: ##STR17## wherein R 4 and R 5 are selected independently from the group consisting of hydrogen and C 1 to C 4 hydrocarbons; X is selected from the group consisting of sulfur, selenium and tellurium; Y - represents an anion of an electrolyte; z represents a number from 0.01 to 1 showing a ratio of the anion per mol of a monomer; and n represents a number of from 5 to 500 showing the degree of polymerization.
Claim 2
Dependent Claim
151 words
A polymer having a structural formula selected from the group consisting of Ia and Ib wherein: ##STR16## R 1 is hydrogen or --OR 3 ; R 2 and R 3 are selected independently from the group consisting of hydrogen and C 1 to C 8 hydrocarbons, with the proviso that R 2 and R 3 may be linked together to form, with both oxygens, a dioxyalkylene substituent on the benzene ring with the formula: ##STR17## wherein R 4 and R 5 are selected independently from the group consisting of hydrogen and C 1 to C 4 hydrocarbons; X is selected from the group consisting of sulfur, selenium and tellurium; Y - represents an anion of an electrolyte; z represents a number from 0.01 to 1 showing a ratio of the anion per mol of a monomer; and n represents a number of from 5 to 500 showing the degree of polymerization.
Claim 3
Dependent Claim
59 words
The polymer of claim 1 wherein R 1 is --OR 3 ; R 2 and R 3 are either (i) selected from the group consisting of methyl and ethyl, or (ii) together with the oxygens form said dioxyalkylene where R 4 and R 5 are selected from the group consisting of hydrogen, methyl and ethyl; and X is sulfur.
Claim 4
Dependent Claim
21 words
The polymer of claim 2 wherein R 2 and R 3 are methyl or ethyl, and R 2 =R 3 .
Claim 5
Dependent Claim
13 words
The polymer of claim 2 wherein R 2 and R 3 are methyl.
Claim 6
Dependent Claim
30 words
The polymer of claim 2 wherein R 2 and R 3 together from said dioxyalkylene, R 4 and R 5 are hydrogen or methyl, and R 4 =R 5 .
Claim 7
Dependent Claim
13 words
The polymer of claim 5 wherein R 4 and R 5 are hydrogen.
Claim 8
Dependent Claim
11 words
The polymer of claim 2 wherein said structural formula is Ia.
Claim 9
Dependent Claim
11 words
The polymer of claim 3 wherein said structural formula is Ia.
Claim 10
Dependent Claim
11 words
The polymer of claim 4 wherein said structural formula is Ia.
Claim 11
Dependent Claim
11 words
The polymer of claim 5 wherein said structural formula is Ia.
Claim 12
Dependent Claim
11 words
The polymer of claim 6 wherein said structural formula is Ia.
Claim 13
Dependent Claim
11 words
The polymer of claim 2 wherein said structural formula is Ib.
Claim 14
Dependent Claim
11 words
The polymer of claim 3 wherein said structural formula is Ib.
Claim 15
Dependent Claim
11 words
The polymer of claim 4 wherein said structural formula is Ib.
Claim 16
Dependent Claim
11 words
The polymer of claim 5 wherein said structural formula is Ib.
Claim 17
Dependent Claim
11 words
The polymer of claim 6 wherein said structural formula is Ib.
Claim 18
Dependent Claim
63 words
The polymer of claim 12 wherein Y - is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 19
Dependent Claim
63 words
The polymer of claim 13 wherein Y - is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 20
Dependent Claim
63 words
The polymer of claim 14 wherein Y - is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 21
Dependent Claim
63 words
The polymer of claim 15 wherein Y - is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 22
Dependent Claim
63 words
The polymer of claim 16 wherein Y - is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 23
Dependent Claim
13 words
The polymer of claim 12 wherein Y - is HSO 4 - .
Claim 24
Dependent Claim
13 words
The polymer of claim 13 wherein Y - is HSO 4 - .
Claim 25
Dependent Claim
13 words
The polymer of claim 14 wherein Y - is HSO 4 - .
Claim 26
Dependent Claim
13 words
The polymer of claim 15 wherein Y - is HSO 4 - .
Claim 27
Dependent Claim
13 words
The polymer of claim 16 wherein Y - is HSO 4 - .
Claim 28
Independent Claim
134 words
A method of preparing a poly(isothianaphthene) polymer by electrochemical polymerization comprising: (a) providing a monomer having the formula: ##STR18## R 1 is hydrogen or --OR 3 ; R 2 and R 3 are selected independently from the group consisting of hydrogen and C 1 to C 8 hydrocarbons, with the proviso that R 2 and R 3 can link together to form, with both oxygens, a dioxyalkylene substituent on the benzene ring with the formula: ##STR19## wherein R 4 and R 5 are selected independently from the group consisting of hydrogen and C 1 to C 4 hydrocarbons; (b) dissolving said monomer in an aprotic solvent containing electrolyte to provide a monomer solution, said electrolyte being ionic and a source of nucleophilic anions; and (c) electrochemically polymerizing said monomer solution to provide a poly(isothianaphthene).
Claim 29
Independent Claim
134 words
A method of preparing a poly(isothianaphthene) polymer by electrochemical polymerization comprising: (a) providing a monomer having the formula: ##STR18## R 1 is hydrogen or --OR 3 ; R 2 and R 3 are selected independently from the group consisting of hydrogen and C 1 to C 8 hydrocarbons, with the proviso that R 2 and R 3 can link together to form, with both oxygens, a dioxyalkylene substituent on the benzene ring with the formula: ##STR19## wherein R 4 and R 5 are selected independently from the group consisting of hydrogen and C 1 to C 4 hydrocarbons; (b) dissolving said monomer in an aprotic solvent containing electrolyte to provide a monomer solution, said electrolyte being ionic and a source of nucleophilic anions; and (c) electrochemically polymerizing said monomer solution to provide a poly(isothianaphthene).
Claim 30
Dependent Claim
10 words
The method of claim 27 wherein said monomer is 5,6-dioxymethylene-isothianaphthene.
Claim 31
Dependent Claim
10 words
The method of claim 27 wherein said monomer is 5,6-dimethoxy-isothianaphthene.
Claim 32
Dependent Claim
19 words
The method of claim 27 wherein said polymerization forms said poly(isothianaphthene) into a membrane on a transparent conductive base.
Claim 33
Dependent Claim
19 words
The method of claim 28 wherein said polymerization forms said poly(isothianaphthene) into a membrane on a transparent conductive base.
Claim 34
Dependent Claim
59 words
An improved electrochromic display device comprising a display electrode, an opposing electrode, a liquid electrolyte therebetween, a housing for the display device which contains said opposing electrode and said liquid electrolyte, and a means for applying voltage across said two electrodes, wherein the improvement comprises a coating on said display electrode formed from the polymeric material of claim 1.
Claim 35
Dependent Claim
25 words
The device of claim 32, wherein the thickness of said coating of polymeric material is in the range of about 0.03 to about 30 microns.
Claim 36
Dependent Claim
25 words
The device of claim 33, wherein the thickness of said coating of polymeric material is in the range of about 0.05 to about 22 microns.
Claim 37
Dependent Claim
25 words
The device of claim 34, wherein the thickness of said coating of polymeric material is in the range of about 0.1 to about 10 microns.
Claim 38
Dependent Claim
20 words
The device of claim 32, wherein said liquid electrolyte comprises a support electrolyte dissolved or dispersed in a suitable solvent.
Claim 39
Dependent Claim
95 words
The device of claim 36, wherein the supporting electrolyte is selected from the group consisting of LiPF 6 , LiSbF 6 , LiAsF 6 , LiClO 4 , NaI, NaPF 6 , NaSbF 6 , NaAsF 6 , NaClO 4 , KI, KPF 6 , KSbF 6 , KAsF 6 , KClO 4 , [(n-Bu) 4 N] + ·ClO 4 - , LiAlCl 4 , LiBF 4 , (C 6 H 5 ) 4 P·BF 4 , (C 6 H 5 ) 4 P·AsF 6 and (C 6 H 5 ) 4 P·ClO 4 .
Claim 40
Dependent Claim
13 words
The device of claim 36, wherein said solvent is an aprotic organic solvent.
Claim 41
Dependent Claim
46 words
The device of claim 38, wherein said solvent is selected from the group consisting of tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, acetonitrile, proprionitrile, 4-methyl-2-pentanone, butyronitrile, valeronitrile, benzonitrile, 1,2-dichloroethane, γ-butyrolactone, valerolactone, dimethoxyethane, methylformate, propylene carbonate, ethylene carbonate, dimethylformamide, dimethyl sulfoxide, ethyl phosphate, methyl phosphate, ethyl phosphite, methyl phosphite and 3-methylsulfolane.
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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) | 1992-01-03 | 1992-07-04 | 1993-01-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-01-03 | 1996-07-04 | 1997-01-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-01-03 | 2000-07-04 | 2001-01-03 | $7700.00 | Window Closed / Lapsed |