Electrochromic element
First Claim
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1. An electrochromic element comprising two electrically conductive substrates, at least one of which is transparent, and an ion conductive substance layer disposed therebetween and comprising a mixture obtained by dispersing an electrochromic substance comprising a compound represented by formula (1) or a derivative thereof;
- formula (1) being represented by the formula;
wherein R1, R2, R3, R4 and R5 are each independently selected from the group consisting of hydrogen and a hydrocarbon residue having from 1 to 20 carbon atoms, Ar1 and Ar2 are each independently a divalent aromatic hydrocarbon residue, and a is an integer of 0 or greater;
into a composition containing a monofunctional acryloyl-modified polyalkylene oxide represented by formula (18) and at least one polyfunctional acryloyl-modified polyalkylene selected from the group consisting of compounds represented by formulae (19) and (20), a polar solvent and a supporting electrolyte;
formula (18), (19) and (20) being represented by the formulae;
wherein R27, R28, and R29 are each independently selected from the group consisting of hydrogen and an alkyl group having from 1 to 5 carbon atoms, R30 is an alkyl group having from 1 to 5 carbon atoms, and j is an integer 2 to 30;
wherein R31, R32, R33, and R34 are each selected from the group consisting of hydrogen and an alkyl group having from 1 to 5 carbon atoms and k is an integer 2 to 30;
wherein R35, R36, and R37 are each selected from the group consisting of hydrogen and an alkyl group having from 1 to 5 carbon atoms, l is an integer of 2 to 30, m is an integer of 2 to 4 and L is a connecting group having a valence corresponding to m.
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Abstract
An electrochromic element composed of an ionically conductive substance layer containing a specified electrochromic substance sandwiched between two electrically conductive substrates at least one of which is transparent.
9 Citations
8 Claims
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1. An electrochromic element comprising two electrically conductive substrates, at least one of which is transparent, and an ion conductive substance layer disposed therebetween and comprising a mixture obtained by dispersing an electrochromic substance comprising a compound represented by formula (1) or a derivative thereof;
- formula (1) being represented by the formula;
wherein R1, R2, R3, R4 and R5 are each independently selected from the group consisting of hydrogen and a hydrocarbon residue having from 1 to 20 carbon atoms, Ar1 and Ar2 are each independently a divalent aromatic hydrocarbon residue, and a is an integer of 0 or greater;
into a composition containing a monofunctional acryloyl-modified polyalkylene oxide represented by formula (18) and at least one polyfunctional acryloyl-modified polyalkylene selected from the group consisting of compounds represented by formulae (19) and (20), a polar solvent and a supporting electrolyte;
formula (18), (19) and (20) being represented by the formulae;
wherein R27, R28, and R29 are each independently selected from the group consisting of hydrogen and an alkyl group having from 1 to 5 carbon atoms, R30 is an alkyl group having from 1 to 5 carbon atoms, and j is an integer 2 to 30;
wherein R31, R32, R33, and R34 are each selected from the group consisting of hydrogen and an alkyl group having from 1 to 5 carbon atoms and k is an integer 2 to 30;
wherein R35, R36, and R37 are each selected from the group consisting of hydrogen and an alkyl group having from 1 to 5 carbon atoms, l is an integer of 2 to 30, m is an integer of 2 to 4 and L is a connecting group having a valence corresponding to m. - View Dependent Claims (2, 3, 4, 5, 6, 7)
N,N,N′ - ,N′
-tetramethylbenzidine, N,N,N′
N′
-tetraethylbenzidine,
N,N,N′
,N′
-tetraphenylbenzidine, N,N,N′
N′
-tetrabenzylbenzidine,N,N,N′
,N′
-tetrapropylbenzidine, N,N,N′
,N′
-tetrabutylbenzidine,N,N′
-diphenyl-N,N′
-ditolylbenzidine, N,N,N′
,N′
-tetratolylbenzidine,N,N′
-diphenyl-N,N′
-dimethylbenzidine,N,N′
-diphenyl-N,N′
-diethylbenzidine,N,N′
-diphenyl-N,N′
-dipropylbenzidine,N-methacrylicethyl-N,N′
,N′
-triethylbenzidine,N-methacrylicethyl-N,N′
,N′
-trimethylbenzidine,N-methacrylicmethyl-N,N′
,N′
-triethylbenzidine,N-methylacrylicmethyl-N,N′
,N′
-trimethylbenzidine,N-methacrylicethyl-N,N′
,N′
-triphenylbenzidine,N-methacrylicphenyl-N,N′
,N′
-trimethylbenzidine,N-methacrylicphenyl-N,N′
,N′
-triethylbenzidine,N-methacrylicphenyl-N,N′
,N′
-triphenylbenzidine,N-methacrylicphenyl-N′
-phenyl-N,N′
-ditolylbenzidine,N-acrylicethyl-N,N′
,N′
-triethylbenzidine,N-acrylicethyl-N,N′
,N′
-trimethylbenzidine,N-acrylicmethyl-N,N′
,N′
-triethylbenzidine,N-acrylicmethyl-N,N′
,N′
-trimethylbenzidine,N-acrylicethyl-N,N′
,N′
-triphenylbenzidine,N-acrylicphenyl-N,N′
,N′
-trimethylbenzidine,N-acrylicphenyl-N,N′
,N′
-triethylbenzidine,N-acrylicphenyl-N,N′
,N′
-triphenylbenzidine,N-acrylicphenyl-N′
-phenyl-N,N′
-ditolylbenzidine,N,N,N′
,N′
-tetraethylphenylenediamine,N,N,N′
,N′
-tetraphenylphenylenediamine,N,N,N′
,N′
-tetrabenzylphenylenediamine,N,N,N′
,N′
-tetrapropylphenylenediamine,N,N,N′
,N′
-tetrabutylphenylenediamine,N,N′
-diphenyl-N,N′
-ditolylphenylenediamine,N,N,N′
,N′
-tetratolylphenylenediamine,N,N′
-diphenyl-N,N′
-dimethylphenylenediamine,N,N′
-diphenyl-N,N′
-diethylphenylenediamine,N,N′
-diphenyl-N,N′
-dipropylphenylenediamine,N-methacrylicethyl-N,N′
,N′
-triethylphenylenediamine,N-methacrylicethyl-N,N′
,N′
-trimethylphenylenediamine,N-methacrylicmethyl-N,N′
,N′
-triethylphenylenediamine,N-methacrylicmethyl-N,N′
,N′
-trimethylphenylenediamine,N-methacrylicethyl-N,N′
,N′
-triphenylphenylenediamine,N-methacrylicphenyl-N,N′
,N′
-trimethylphenylenediamine,N-methacrylicphenyl-N,N′
,N′
-triethylphenylenediamine,N-methacrylicphenyl-N,N′
,N′
-triphenylphenylenediamine,N-methacrylicphenyl-N′
-phenyl-N,N′
-ditolylphenylenediamine,N-acrylicethyl-N,N′
,N′
-triethylphenylenediamine,N-acrylicethyl-N,N′
,N′
-trimethylphenylenediamine,N-acrylicmethyl-N,N′
,N′
-triethylphenylenediamine,N-acrylicmethyl-N,N′
,N′
-trimethylphenylenediamine,N-acrylicethyl-N,N′
,N′
-triphenylphenylenediamine,N-acrylicphenyl-N,N′
,N′
-trimethylphenylenediamine,N-acrylicphenyl-N,N′
,N′
-triethylphenylenediamine,N-acrylicphenyl-N,N′
,N′
-triphenylphenylenediamine,N-acrylicphenyl-N′
-phenyl-N,N′
-ditolylphenylenediamine.
- formula (1) being represented by the formula;
-
3. The electrochromic element according to claim 1 wherein the ion conductive substance layer further contains a compound having a viologen structure represented by the formula
wherein X− - and Y−
are the same or different and are each a counter anion selected from group consisting of a halogen anion, ClO4−
, BF4−
, PF6−
, CH3COO−
and CH3(C6H4)SO3−
.
- and Y−
-
4. The electrochromic element according to claim 3 wherein the compound having a viologen structure of formula (2) is selected from the group consisting of
N,N′ - -diheptylbipyridiniumdibromide,
N,N′
-diheptylbipyridiniumdichloride,N,N′
-diheptylbipyridiniumdiperchlorate,N,N′
-diheptylbipyridiniumtetrafluoroborate,N,N′
-diheptylbipyridiniumhexafluorophosphate,N,N-dihexylbipyridiniumdibromide, N,N′
-dihexylbipyridiniumdichloride,N,N′
-dihexylbipyridiniumdiperchlorate,N,N′
-dihexylbipyridiniumtetrafluoroborate,N,N′
-dihexylbipyridiniumdihexafluorophosphate,N,N′
-dipropylbipyridiniumdibromide, N,N′
-dipropylbipyridiniumdichloride,N,N′
-dipropylbipyridiniumdiperchlorate,N,N′
-dipropylbipyridiniumtetrafluoroborate,N,N′
-dipropylbipyridiniumdihexafluorophosphate,N,N′
-dibenzylbipyridiniumdibromide,N,N′
-dibenzylbipyridiniumperchlorate,N,N′
-dibenzylbipyridiniumtetrafluoroborate,N,N′
-dibenzylbipyridiniumdihexafluorophosphate,N,N′
-dimethacryloylethylbipyridiniumdibromide,N,N′
-dimethacryloylethylbipyridiniumdichloride,N,N′
-dimethacryloylethylbipyridiniumdiperchlorate,N,N′
-dimethacryloylethylbipyridiniumditetrafluoroborate,N,N′
-dimethacryloylethylbipyridiniumdihexafluorophosphate,N,N′
-diacryloylethylbipyridiniumdibromide,N,N′
-diacryloylethylbipyridiniumdichloride,N,N′
-diacryloylethylbipyridiniumdiperchlorate,N,N′
-diacryloylethylbipyridiniumditetrafluoroborate,N,N′
-diacryloylethylbipyridiniumdihexafluorophosphate,N,N′
-dimethacryloylmethylbipyridiniumdibromide,N,N′
-dimethacryloylmethylbipyridiniumdichloride,N,N′
-dimethacryloylmethylbipyridiniumdiperchlorate,N,N′
-dimethacryloylmethylbipyridiniumditetrafluoroborate,N,N′
-dimethacryloylmethylbipyridiniumdihexafluorophosphate,N,N′
-diacryloylmethylbipyridiniumdibromide,N,N′
-diacryloylmethylbipyridiniumdiperchlorate,N,N′
-diacryloylmethylbipyridiniumditetrafluoroborate,N,N′
-diacryloylmethylbipyridiniumdihexafluorophosphate,N-heptyl-N′
-methacryloylethylbipyridiniumdibromide,N-heptyl-N′
-methacryloylethylbipyridiniumdichloride,N-heptyl-N′
-methacryloylethylbipyridiniumdiperchlorate,N-heptyl-N′
-methacryloylethylbipyridiniumtetrafluoroborate,N-heptyl-N′
-methacryloylethylbipyridiniumdihexafluorophosphate,N-hexyl-N′
-methacryloylethylbipyridiniumdibromide,N-hexyl-N′
-methacryloylethylbipyridiniumdichloride,N-hexyl-N′
-methacryloylethylbipyridiniumdiperchlorate,N-hexyl-N′
-methacryloylethylbipyridiniumtetrafluoroborate,N-hexyl -N′
-methacryloylethylbipyridiniumdihexafluorophosphate,N-benzyl-N′
-methacryloylethylbipyridiniumdibromide,N-benzyl-N′
-methacryloylethylbipyridiniumdichloride,N-benzyl-N′
-methacryloylethylbipyridiniumdiperchlorate,N-benzyl-N′
-methacryloylethylbipyridiniumtetrafluoroborate,N-benzyl-N′
-methacryloylethylbipyridiniumdihexafluorophosphate,N-butyl-N′
-methacryloylethylbipyridiniumdibromide,N-butyl-N′
-methacryloylethylbipyridiniumdichloride,N-butyl-N′
-methacryloylethylbipyridiniumdiperchlorate,N-butyl-N′
-methacryloylethylbipyridiniumtetrafluoroborate,N-butyl-N′
-methacryloylethylbipyridiniumdihexafluorophosphate,N-propyl-N′
-methacryloylethylbipyridiniumdibromide,N-propyl-N′
-methacryloylethylbipyridiniumdichloride,N-propyl-N′
-methacryloylethylbipyridiniumdiperchlorate,N-propyl-N′
-methacryloylethylbipyridiniumtetrafluoroborate,N-propyl-N′
-methacryloylethylbipyridiniumdihexafluorophosphate,N-heptyl-N′
-methacryloylmethylbipyridiniumdibromide,N-heptyl-N′
-methacryloylmethylbipyridiniumdichloride,N-heptyl-N′
-methacryloylmethylbipyridiniumdiperchlorate,N-heptyl-N′
-methacryloylmethylbipyridiniumtetrafluoroborate,N-heptyl-N′
-methacryloylmethylbipyridiniumdihexafluorophosphate,N-hexyl-N′
-methacryloylmethylbipyridiniumdibromide,N-hexyl-N′
-methacryloylmethylbipyridiniumdichloride,N-hexyl-N′
-methacryloylmethylbipyridiniumdiperchlorate,N-hexyl-N′
-methacryloylmethylbipyridiniumtetrafluoroborate,N-hexyl-N′
-methacryloylmethylbipyridiniumdihexafluorophosphate,N-benzyl-N′
-methacryloylmethylbipyridiniumdibromide,N-benzyl-N′
-methacryloylmethylbipyridiniumdichloride,N-benzyl-N′
-methacryloylmethylbipyridiniumdiperchlorate,N-benzyl-N′
-methacryloylmethylbipyridiniumtetrafluoroborate,N-benzyl-N′
-methacryloylmethylbipyridiniumdihexafluorophosphate,N-butyl-N′
-methacryloylmethylbipyridiniumdibromide,N-butyl-N′
-methacryloylmethylbipyridiniumdichloride,N-butyl-N′
-methacryloylmethylbipyridiniumdiperchlorate,N-butyl-N′
-methacryloylmethylbipyridiniumtetrafluoroborate,N-butyl-N′
-methacryloylmethylbipyridiniumdihexafluorophosphate,N-propyl-N′
-methacryloylmethylbipyridiniumdibromide,N-propyl-N′
-methacryloylmethylbipyridiniumdichloride,N-propyl-N′
-methacryloylmethylbipyridiniumdiperchlorate,N-propyl-N′
-methacryloylmethylbipyridiniumtetrafluoroborate,N-propyl-N′
-methacryloylmethylbipyridiniumdihexafluorophosphate,N-heptyl-N′
-methacryloylphenylbipyridiniumdibromide,N-heptyl-N′
-methacryloylphenylbipyridiniumdichloride,N-heptyl-N′
-methacryloylphenylbipyridiniumdiperchlorate,N-heptyl-N′
-methacryloylphenylbipyridiniumtetrafluoroborate,N-heptyl-N′
-methacryloylphenylbipyridiniumdihexafluorophosphate,N-hexyl-N′
-methacryloylphenylbipyridiniumdibromide,N-hexyl-N′
-methacryloylphenylbipyridiniumdichloride,N-hexyl-N′
-methacryloylphenylbipyridiniumdiperchlorate,N-hexyl-N′
-methacryloylphenylbipyridiniumtetrafluoroborate,N-hextyl-N′
-methacryloylphenylbipyridiniumdihexafluorophosphate,N-benzyl-N′
-methacryloylphenylbipyridiniumdibromide,N-benzyl-N′
-methacryloylphenylbipyridiniumdichloride,N-benzyl-N′
-methacryloylphenylbipyridiniumdiperchlorate,N-benzyl-N′
-methacryloylphenylbipyridiniumtetrafluoroborate,N-benzyl-N′
-methacryloylphenylbipyridiniumdihexafluorophosphate,N-butyl-N′
-methacryloylphenylbipyridiniumdibromide,N-butyl-N′
-methacryloylphenylbipyridiniumdichloride,N-butyl-N′
-methacryloylphenylbipyridiniumdiperchlorate,N-butyl-N′
-methacryloylphenylbipyridiniumtetrafluoroborate,N-butyl-N′
-methacryloylphenylbipyridiniumdihexafluorophosphate,N-propyl-N′
-methacryloylphenylbipyridiniumdibromide,N-propyl-N′
-methacryloylphenylbipyridiniumdichloride,N-propyl-N′
-methacryloyiphenylbipyridiniumdiperchlorate,N-propyl-N′
-methacryloylphenylbipyridiniumtetrafluoroborate, andN-propyl-N′
-methacryloylphenylbipyridiniumdihexafluorophosphate.
- -diheptylbipyridiniumdibromide,
-
5. The electrochromic element according to claim 1 wherein the polar solvent is an organic polar solvent selected from the group consisting of methanol, ethanol, propylene carbonate, ethylene carbonate, dimethylsulfoxide, dimethoxyethane, acetonitrile, γ
- -butyrolactone, γ
-valerolactone, sulforan, dimethylformamide, dimethoxyethane, tetrahydrofuran, propionitrile, glutaronitrile, adiponitrile, methoxyacetonitrile, dimethylacetoamide, methylpyrrolidinone, dimethylsulfoxide, dioxolane, trimethylphosphate, and polyethylene glycol.
- -butyrolactone, γ
-
6. The electrochromic element according to claim 1 wherein the supporting electrolyte is selected from the group consisting of alkali metal salts, alkaline earth metal salts, quaternary ammonium salts, and cyclic quaternary ammonium salts.
-
7. The electrochromic device according to claim 1 wherein the amount of the polar solvent contained in the layer is in a range of 100 to 800 weight % based on a total amount of the monofunctional acryloyl-modified polyalkylene oxide and the polyfunctional acryloyl-modified polyalkylene oxide.
-
8. An electrochromic element comprising two conductive substrates, at least one of which is transparent, and an ion conductive substance layer disposed therebetween and containing an electrochromic substance represented by the formula (1) below or a derivative thereof;
-
formula (1) being represented by the formula wherein R1, R2, R3, R4 and R5 are each selected from the group consisting of hydrogen and a hydrocarbon residue having from 1 to 20 carbon atoms and are the same or different, Ar1 and Ar2 are each a divalent aromatic hydrocarbon residue and are the same or different and a is an integer of 0 or greater and wherein the ion conductive substance comprises a mixture obtained by dispersing the electrochromic substance into a composition containing an urethaneacrylate represented by formula (3) below, a polar solvent and a supporting electrolyte;
formula (3) being represented by the formulawherein R6 and R7 are the same or different and are each a group of formula (4), (5) or (6) below, R8 and R9 are the same or different and are each a C1-C20 divalent hydrocarbon residue, Y is selected from the group consisting of a polyether unit, a polyester unit, a polycarbonate unit and mixed units thereof and b is an integer from 1 to 100; formulae (4), (5) and (6) being represented by the formulae wherein R10, R11 and R12 are the same or different and are each selected from the group consisting of a hydrogen atom and a C1-C3 alkyl group and R13 is a C1-C20 organic residue of divalent through quatervalent.
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Specification
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Current AssigneeNippon Mitsubishi Oil Corporation (ENEOS Holdings, Inc.)
-
Original AssigneeNippon Mitsubishi Oil Corporation (ENEOS Holdings, Inc.)
-
InventorsSugiura, Izuru, Kobayashi, Masaaki, Nishikitani, Yoshinori
-
Primary Examiner(s)Jones, Deborah
-
Assistant Examiner(s)XU, LING X
-
Application NumberUS09/594,494Time in Patent Office999 DaysField of Search359/265, 359/270, 359/273, 359/272, 428/411.1, 428/500, 428/689, 428/515, 428/702, 428/704, 252/582, 252/586US Class Current359/265CPC Class CodesC09K 2211/1007 Non-condensed systemsC09K 2211/1014 bridged by heteroatoms, e.g...C09K 2211/1029 containing one nitrogen ato...C09K 9/02 Organic tenebrescent materialsG02F 1/1503 caused by oxidation-reducti...Y10T 428/31504 Composite [nonstructural la...Y10T 428/31855 Of addition polymer from un...Y10T 428/31909 Next to second addition pol...
