Electrochromic salts, solutions, and devices
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Abstract
Electrochromic salts. Electrochromic salts of dicationic viologens such as methyl viologen and benzyl viologen associated with anions selected from bis(trifluoromethylsulfonyl)imide, bis(perfluoroethylsulfonyl)imide, and tris(trifluoromethylsulfonyl)methide are produced by metathesis with the corresponding viologen dihalide. They are highly soluble in molten quarternary ammonium salts and together with a suitable reductant provide electrolyte solutions that are used in electrochromic windows.
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Citations
36 Claims
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1-6. -6. (canceled)
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7. An electrolyte solution for an electrochromic device, comprising:
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(a) a molten salt solvent comprising at least one anion selected from the group consisting of bis(trifluoromethylsulfonyl)imide, bis(perfluoroethylsulfonyl)imide, and tris(trifluoromethylsulfonyl)methide;
(b) at least one reductant soluble in said molten salt solvent; and
(c) at least one oxidant soluble in said molten salt solvent, said oxidant having the chemical formula [A][B]2 wherein B is selected from the group consisting of bis(trifluoromethylsulfonyl)imide, bis(perfluoroethylsulfonyl)imide, and tris(trifluoromethylsulfonyl)methide and wherein A is a dication having the structural formula wherein R1 and R1′
are independently selected from alkyl having 1-20 carbons, aryl, alkyl-substituted aryl having 7-20 carbons, methoxy-substituted aryl having 7-20 carbons, nitro-substituted aryl having 6-20 carbons, cyano-substituted aryl having 7-20 carbons, trifluoromethyl-substituted aryl having 7-20 carbons;
wherein R2, R2′
, R3 and R3′
are independently selected from hydrogen, alkyl having 1-20 carbons, aryl, alkyl-substituted aryl having 7-20 carbons, methoxy-substituted aryl having 7-20 carbons, nitro-substituted aryl having 6-20 carbons, cyano-substituted aryl having 7-20 carbons, trifluoromethyl-substituted aryl having 7-20 carbons;
or wherein A is a dication having the structural formula wherein R4 and R4′
are independently selected from alkyl having 1-20 carbons;
wherein R5, R5′
, R6, R6′
, R7, R7′
, R8, and R8′
are independently selected from hydrogen, alkyl having 1-20 carbons, aryl, alkyl-substituted aryl having 7-20 carbons, methoxy-substituted aryl having 7-20 carbons, nitro-substituted aryl having 6-20 carbons, cyano-substituted aryl having 7-20 carbons, trifluoromethyl-substituted aryl having 7-20 carbons;
or wherein A is a dication having the structural formula wherein n is 2-7;
wherein R9 and R9′
are independently selected from alkyl having 1-20 carbons;
wherein R10, R10′
, R11, R11′
, R12, and R12′
independently selected from hydrogen, alkyl having 1-20 carbons, aryl, alkyl-substituted aryl having 7-20 carbons, methoxy-substituted aryl having 7-20 carbons, nitro-substituted aryl having 6-20 carbons, cyano-substituted aryl having 7-20 carbons, trifluoromethyl-substituted aryl having 7-20 carbons;
or wherein A is a dication having the structural formula wherein R13, R13′
, R14, R14′
, R15, R15′
, R16, and R16′
are independently selected from hydrogen, alkyl having 1-20 carbons, aryl, alkyl-substituted aryl having 7-20 carbons, methoxy-substituted aryl having 7-20 carbons, nitro-substituted aryl having 6-20 carbons, cyano-substituted aryl having 7-20 carbons, trifluoromethyl-substituted aryl having 7-20 carbons;
or wherein A is a dication having the structural formula wherein R17 and R18 are independently selected from alkyl having 1-20 carbons, alkyl-substituted aryl having 7-20 carbons, methoxy-substituted aryl having 7-20 carbons, nitro-substituted aryl having 6-20 carbons, cyano-substituted aryl having 7-20 carbons, trifluoromethyl-substituted aryl having 7-20 carbons;
wherein R119, R20, R21, R22, and R23 are independently selected from alkyl having 1-20 carbons, alkyl-substituted aryl having 7-20 carbons, methoxy-substituted aryl having 7-20 carbons, nitro-substituted aryl having 6-20 carbons, cyano-substituted aryl having 7-20 carbons, trifluoromethyl-substituted aryl having 7-20 carbons. - View Dependent Claims (8, 9, 10, 11, 12, 13, 14, 15, 16)
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17-26. -26. (canceled)
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27. An electrolyte solution prepared by dissolving at least one reductant and at least one electrochromic ionic compound into a molten salt, said molten salt comprising an anion selected from the group consisting of bis(trifluoromethylsulfonyl)imide, bis(perfluoroethylsulfonyl)imide, and tris(trifluoromethylsulfonyl)methide, said electrochromic compound having the chemical formula
[A][B]2wherein B is selected from the group consisting of bis(trifluoromethylsulfonyl)imide, bis(perfluoroethylsulfonyl)imide, and tris(trifluoromethylsulfonyl)methide and wherein A is a dication having the structural formula
Specification