US5336448A
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Electrochromic devices with bipyridinium salt solutions
Assignee: Gentex Corp
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Filing: 1991-06-25
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Granted: 1994-08-09
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Expires: 2011-06-25
Abstract
Abstract The present invention provides solution-phase electrochromic devices, including such devices that are single-compartment and self-erasing, in which the media of variable transmittance are solutions comprising, as cathodic electrochromic compounds, certain 4,4'-bipyridinium salts, such as salts of 1,1'-dibenzyl-2,2',6,6'-tetraalkyl-4,4'-bipyridinium cations. Electrochromic devices of the invention are components of variable transmittance in display devices, windows and other types of light filters, and variable reflectance mirrors, such as those that can be used as dimmable rearview mirrors in motor vehicles.
Inventors
- 👤 Harlan J. Byker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 11:01
CPC Classifications
C; C09; C09K; C09K9/00; C09K9/02; G; G02; G02F; G02F1/00; G02F1/01; G02F1/15; G02F1/1503; G02F2001/1502; G02F1/1514; G02F2001/15145
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
78 words
A solution-phase electrochromic device in which the solution of variable transmittance comprises a solvent, which is a liquid at room temperature, and a salt of a cation of Formula XVII ##STR10## wherein R 36 and R 37 are independently selected from the group consisting of benzyl and alkyl of 1-20 carbon atoms; and R 34 , R 35 , R 38 and R 39 are independently selected from the group consisting of alkyl groups of 1-4 carbon atoms.
Claim 2
Dependent Claim
78 words
A solution-phase electrochromic device in which the solution of variable transmittance comprises a solvent, which is a liquid at room temperature, and a salt of a cation of Formula XVII ##STR10## wherein R 36 and R 37 are independently selected from the group consisting of benzyl and alkyl of 1-20 carbon atoms; and R 34 , R 35 , R 38 and R 39 are independently selected from the group consisting of alkyl groups of 1-4 carbon atoms.
Claim 3
Dependent Claim
22 words
A device of claim 1 wherein, in the cation of the salt in the solution, R 36 and R 37 are benzyl.
Claim 4
Dependent Claim
28 words
A device of claim 1 wherein, in the cation of the salt in the solution, R 34 , R 35 , R 38 and R 39 are methyl.
Claim 5
Dependent Claim
17 words
A device of claim 2 wherein, in the solution, the cation of the salt is 1,1 '-dibenzyl-2,2',6,6'-tetramethyl-4,4'-bipyridinium.
Claim 6
Dependent Claim
41 words
A device of claim 2 wherein, in the solution, the solvent consists essentially of propylene carbonate, gamma-butyrolactone, gamma-valerolactone, or an homogeneous mixture of any two or more of said solvents or any one or more of said solvents with ethylene carbonate.
Claim 7
Dependent Claim
41 words
A device of claim 3 wherein, in the solution, the solvent consists essentially of propylene carbonate, gamma-butyrolactone, gamma-valerolactone, or an homogeneous mixture of any two or more of said solvents or any one or more of said solvents with ethylene carbonate.
Claim 8
Dependent Claim
41 words
A device of claim 4 wherein, in the solution, the solvent consists essentially of propylene carbonate, gamma-butyrolactone, gamma-valerolactone, or an homogeneous mixture of any two or more of said solvents or any one or more of said solvents with ethylene carbonate.
Claim 9
Dependent Claim
16 words
A device of claim 5 wherein, in the solution, the solvent consists essentially of propylene carbonate.
Claim 10
Dependent Claim
16 words
A device of claim 6 wherein, in the solution, the solvent consists essentially of propylene carbonate.
Claim 11
Dependent Claim
16 words
A device of claim 7 wherein, in the solution, the solvent consists essentially of propylene carbonate.
Claim 12
Independent Claim
24 words
A device of any of claims 1-10 wherein, in the solution, the concentration of the cation of Formula XVII is from 0.001M to 0.1M.
Claim 13
Dependent Claim
39 words
A device of claim 11 wherein, in the solution, the anions of the salt of the cation of Formula XVII are selected from the group consisting of BF 4 - , PF 6 - and ClO 4 - .
Claim 14
Dependent Claim
20 words
A device of claim 12 wherein, in the solution, the salt of the cation of Formula XVII is 1,1'-dibenzyl-2,2',6,6'-tetramethyl-4,4'-bipyridinium difluoroborate.
Claim 15
Dependent Claim
108 words
A solution-phase electrochromic device in which the solution of variable transmittance comprises a solvent; an anodic electrochromic compound which, upon oxidation of its zero-potential equilibrium state, undergoes an increase in molar extinction coefficient at at least one wavelength in the visible range; and a cathodic electrochromic compound which is a salt of a cation of Formula IV ##STR11## wherein R 7 and R 8 are independently selected from the group consisting of an alkyl group with 1-20 carbon atoms and benzyl; and R 9 , R 10 , R 11 , and R 12 are independently selected from the group consisting of alkyl groups with 1-4 carbon atoms.
Claim 16
Dependent Claim
108 words
A solution-phase electrochromic device in which the solution of variable transmittance comprises a solvent; an anodic electrochromic compound which, upon oxidation of its zero-potential equilibrium state, undergoes an increase in molar extinction coefficient at at least one wavelength in the visible range; and a cathodic electrochromic compound which is a salt of a cation of Formula IV ##STR11## wherein R 7 and R 8 are independently selected from the group consisting of an alkyl group with 1-20 carbon atoms and benzyl; and R 9 , R 10 , R 11 , and R 12 are independently selected from the group consisting of alkyl groups with 1-4 carbon atoms.
Claim 17
Dependent Claim
11 words
A device according to claim 14 which is single-compartment and self-erasing.
Claim 18
Dependent Claim
42 words
A device according to claim 15 wherein, in the solution, the solvent consists essentially of propylene carbonate, gamma-butyrolactone, gamma-valerolactone, or an homogeneous mixture of any two or more of said solvents or any one or more of said solvents with ethylene carbonate.
Claim 19
Dependent Claim
17 words
A device according to claim 16 wherein, in the solution, the solvent consists essentially of propylene carbonate.
Claim 20
Dependent Claim
96 words
A device according to claim 14 wherein, in the solution, the cathodic compound is a salt of a cation of Formula XLV ##STR12## wherein R 13 is alkyl of 1-4 carbon atoms or benzyl, and R 14 and R 15 are independently selected from the group consisting of alkyl groups of 1-4 carbon atoms, and the anions of the salt are selected from the group consisting of BF 4 - , PF 6 - and ClO 4 - ; and the anodic compound is selected from the group consisting of 5,10-dihydro-5,10-dimethylphenazine, N,N,N',N'-tetramethyl-p-phenylenediamine, N,N,N',N'-tetraphenyl-p-phenylenediamine, and bis-3,3'-diethyl-2,2'-benzothiazole azine.
Claim 21
Dependent Claim
96 words
A device according to claim 15 wherein, in the solution, the cathodic compound is a salt of a cation of Formula XLV ##STR13## wherein R 13 is alkyl of 1-4 carbon atoms or benzyl, and R 14 and R 15 are independently selected from the group consisting of alkyl groups of 1-4 carbon atoms, and the anions of the salt are selected from the group consisting of BF 4 - , PF 6 - and ClO 4 - ; and the anodic compound is selected from the group consisting of 5,10-dihydro-5,10-dimethylphenazine, N,N,N',N'-tetramethyl-p-phenylenediamine, N,N,N',N'-tetraphenyl-p-phenylenediamine, and bis-3,3'-diethyl-2,2'-benzothiazole azine.
Claim 22
Dependent Claim
96 words
A device according to claim 16 wherein, in the solution, the cathodic compound is a salt of a cation of Formula XLV ##STR14## wherein R 13 is alkyl of 1-4 carbon atoms or benzyl, and R 14 and R 15 are independently selected from the group consisting of alkyl groups of 1-4 carbon atoms, and the anions of the salt are selected from the group consisting of BF 4 - , PF 6 - and ClO 4 - ; and the anodic compound is selected from the group consisting of 5,10-dihydro-5,10-dimethylphenazine, N,N,N',N'-tetramethyl-p-phenylenediamine, N,N,N',N'-tetraphenyl-p-phenylenediamine, and bis-3,3'-diethyl-2,2'-benzothiazole azine.
Claim 23
Dependent Claim
96 words
A device according to claim 17 wherein, in the solution, the cathodic compound is a salt of a cation of Formula XLV ##STR15## wherein R 13 is alkyl of 1-4 carbon atoms or benzyl, and R 14 and R 15 are independently selected from the group consisting of alkyl groups of 1-4 carbon atoms, and the anions of the salt are selected from the group consisting of BF 4 - , PF 6 - and ClO 4 - ; and the anodic compound is selected from the group consisting of 5,10-dihydro-5,10-dimethylphenazine, N,N,N',N'-tetramethyl-p-phenylenediamine, N,N,N',N'-tetraphenyl-p-phenylenediamine, and bis-3,3'-diethyl-2,2'-benzothiazole azine.
Claim 24
Dependent Claim
15 words
A device according to claim 18 wherein, in the solution, the anodic compound is 5,10-dihydro-5,10-dimethylphenazine.
Claim 25
Dependent Claim
15 words
A device according to claim 19 wherein, in the solution, the anodic compound is 5,10-dihydro-5,10-dimethylphenazine.
Claim 26
Dependent Claim
15 words
A device according to claim 20 wherein, in the solution, the anodic compound is 5,10-dihydro-5,10-dimethylphenazine.
Claim 27
Dependent Claim
15 words
A device according to claim 21 wherein, in the solution, the anodic compound is 5,10-dihydro-5,10-dimethylphenazine.
Claim 28
Dependent Claim
20 words
A device according to claim 22 wherein, in the solution, in the cation of Formula XLV, R 13 is benzyl.
Claim 29
Dependent Claim
32 words
A device according to claim 26 wherein, in the solution, in the cation of Formula XLV, R 14 and R 15 are methyl and the salt of said cation is the difluoroborate.
Claim 30
Dependent Claim
20 words
A device according to claim 23 wherein, in the solution, in the cation of Formula XLV, R 13 is benzyl.
Claim 31
Dependent Claim
32 words
A device according to claim 28 wherein, in the solution, in the cation of Formula XLV, R 14 and R 15 are methyl and the salt of said cation is the difluoroborate.
Claim 32
Dependent Claim
20 words
A device according to claim 24 wherein, in the solution, in the cation of Formula XLV, R 13 is benzyl.
Claim 33
Dependent Claim
32 words
A device according to claim 30 wherein, in the solution, in the cation of Formula XLV, R 14 and R 15 are methyl and the salt of said cation is the difluoroborate.
Claim 34
Dependent Claim
20 words
A device according to claim 25 wherein, in the solution, in the cation of Formula XLV, R 13 is benzyl.
Claim 35
Dependent Claim
32 words
A device according to claim 32 wherein, in the solution, in the cation of Formula XLV, R 14 and R 15 are methyl and the salt of said cation is the difluoroborate.
Claim 36
Independent Claim
32 words
A device according to any of claims 20, 21, and 24-33 wherein, in the solution, the concentrations of the cathodic electrochromic compound and the anodic electrochromic compound are from 0.001M to 0.1M.
Claim 37
Dependent Claim
18 words
A device acccording to claim 34 wherein the solution is thickened with 1 wt. %-10 wt. % polymethymethacrylate.
Claim 38
Independent Claim
18 words
A device according to any of claims 20, 21, and 24-33 wherein the solution comprises a UV-stabilizing compound.
Claim 39
Dependent Claim
32 words
A device according to claim 36 which comprises, in the solution at a concentration from 0.1M to 0.6M, an alkyl ester of 2-cyano-3,3-diphenyl acrylate, wherein the alkyl group has 1-10 carbon atoms.
Claim 40
Dependent Claim
14 words
A device according to claim 37 wherein the alkyl ester is ethyl 2-cyano-3,3-diphenyl acrylate.
Claim 41
Dependent Claim
18 words
A device according to claim 38 wherein the solution is thickened with 1 wt. %-10 wt. % polymethymethacrylate.
Claim 42
Dependent Claim
19 words
A device according to claim 39 which is the component of variable transmittance in a variable transmittance light filter.
Claim 43
Dependent Claim
20 words
A device according to claim 14 which is the component of variable transmittance in a variable reflectance, rearview motor-vehicle mirror.
Claim 44
Dependent Claim
20 words
A device according to claim 39 which is the component of variable transmittance in a variable reflectance, rearview motor-vehicle mirror.
References Cited (Backward Citations)
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