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US-12619116-B2 - Electrochromic devices including polymers having residues of ((meth)acrylate-amine cation bis(substituted-sulfonyl)imide anion)) monomer

US12619116B2US 12619116 B2US12619116 B2US 12619116B2US-12619116-B2

Abstract

The present invention relates to electrochromic devices and compositions that include a polymer that includes residues of, or a polymerizable composition that includes, ((meth)acrylate-amine cation bis(substituted-sulfonyl)imide anion)) monomer represented by the following Formula (I), With reference to Formula (I): R 1 is in each case independently hydrogen or methyl; R 2 is in each case independently a single bond, a divalent linear or branched alkane, or divalent linear or branched cycloalkane; Y + is in each case independently an amine cation, such as for example —N(R 3 )(R 4 )(R 5 ) + ; and X − is a bis(substituted-sulfonyl)imide anion represented by the following Formula (II),

Inventors

  • DYLAN THOMAS CHRISTIANSEN
  • Ivan Alexandrovich Sokol

Assignees

  • VITRO FLAT GLASS LLC

Dates

Publication Date
20260505
Application Date
20230411

Claims (20)

  1. 1 . An electrochromic device comprising: (a) a first substrate having a surface comprising a first transparent electrode layer; (b) a second substrate having a surface comprising a second transparent conductive electrode layer, wherein said first transparent electrode layer and said second transparent electrode layer are in opposing spaced opposition; and (c) an electrochromic layer interposed between said first transparent electrically conductive electrode layer and said second transparent electrically conductive electrode layer, wherein said electrochromic layer comprises, (i) a cathodic component, (ii) an anodic component, (iii) an optional electrolyte, and (iv) a polymer matrix, wherein said polymer matrix comprises a polymer, wherein said polymer comprises residues of a monomer represented by the following Formula (I), wherein for Formula (I), R 1 is in each case independently hydrogen or methyl, R 2 is in each case independently a single bond, a divalent linear or branched alkane, or divalent linear or branched cycloalkane, Y + is in each case independently represented by one of the following Formulas (A), (B), (C), (D), (E), (F), and (G), wherein independently for each of Formulas (A), (B), (C), (D), (E), (F), and (G), R 3 , R 4 , and R 5 are in each case independently selected from linear or branched alkyl or cycloalkyl, and X − is in each case independently represented by the following Formula (II), wherein for Formula (II), R 6 and R 7 are each independently selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, wherein said anodic component comprises an anodic component anion represented by the following Formula (IV), and optionally an anodic component anion represented by the following Formula (III), wherein for Formula (IV), R 9 is selected from divalent linear or branched alkane linking group, and R 10 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and wherein for Formula (III), R 8 is selected from divalent linear or branched alkane linking group.
  2. 2 . The electrochromic device of claim 1 , wherein for Formula (I), R 2 is independently in each case a single bond, a divalent linear or branched C 1 -C 10 alkane, or divalent linear or branched C 3 -C 7 cycloalkane, independently for each of Formulas (A), (B), (C), (D), (E), (F), and (G), R 3 , R 4 , and R 5 are in each case independently selected from linear or branched C 1 -C 10 alkyl or C 3 -C 7 cycloalkyl, and for Formula (II), R 6 and R 7 are each independently selected from fluorine, linear or branched C 1 -C 10 fluorinated alkyl, or linear or branched C 1 -C 10 perfluorinated alkyl.
  3. 3 . The electrochromic device of claim 1 , wherein for Formula (I), R 2 is independently in each case a single bond or a divalent linear or branched C 1 -C 6 alkane, independently for each of Formulas (A), (B), (C), (D), (E), (F), and (G), R 3 , R 4 , and R 5 are in each case independently selected from linear or branched C 1 -C 6 alkyl, and for Formula (II), R 6 and R 7 are each independently selected from linear or branched C 1 -C 6 perfluorinated alkyl.
  4. 4 . The electrochromic device of claim 1 , wherein said polymer, of said polymer matrix, further comprises residues of a comonomer comprising at least one of linear or branched alkyl (meth)acrylate, cycloalkyl (meth)acrylate, or polyfunctional monomer comprising at least two (meth)acrylate groups.
  5. 5 . The electrochromic device of claim 1 , wherein said polymer, of said polymer matrix, is formed by polymerizing a monomer composition comprising said monomer represented by Formula (I) between said first transparent electrically conductive electrode layer and said second transparent electrically conductive electrode layer.
  6. 6 . The electrochromic device of claim 1 , wherein for Formula (III), R 8 is selected from divalent linear or branched C 1 -C 10 alkane linking group, and for Formula (IV), R 9 is selected from divalent linear or branched C 1 -C 10 alkane linking group, and R 10 is selected from fluorine, linear or branched C 1 -C 10 fluorinated alkyl, or linear or branched C 1 -C 10 perfluorinated alkyl.
  7. 7 . The electrochromic device of claim 1 , wherein said anodic component further comprises a counter-cation.
  8. 8 . The electrochromic device of claim 7 , wherein each counter-cation is independently selected from tetra(linear or branched alkyl) ammonium cation.
  9. 9 . The electrochromic device of claim 1 , wherein said cathodic component comprises at least one of a 1,1′-disubstituted-4,4′-dipyridinium cation represented by the following Formula (V), or a 1,1-(alkane-alpha, omega-diyl)-bis-(1′-substituted-4,4′-dipyridinium) cation represented by the following Formula (VI), wherein for Formula (V), R 11 and R 12 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cyloalkyl, unsubstituted aryl, and substituted aryl, and for Formula (VI), R 13 and R 15 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cyloalkyl, unsubstituted aryl, and substituted aryl, and R 14 is selected from divalent linear or branched C 1 -C 10 alkane linking group.
  10. 10 . The electrochromic device of claim 9 , wherein said cathodic component further comprises counter-anions, wherein each counter-anion of the cathodic component is selected from the group consisting of BF 4 − , PF 6 − , ClO 4 − , CF 3 SO 3 —, (CF 3 SO 2 ) 2 N − , (CF 3 SO 2 ) 3 C − , and B(phenyl) 4 − .
  11. 11 . The electrochromic device of claim 1 , wherein said electrolyte is present and comprises, at least one electrolyte anion, wherein each electrolyte anion is independently selected from bis(perfluoro(linear or branched C 1 -C 6 alkysulfonyl)imide, and at least one electrolyte cation, wherein each electrolyte cation is independently selected from 1-(linear or branched C 1 -C 6 alkyl)-3-(linear or branched C 1 -C 6 alkyl)imidazolium, 1-(linear or branched C 1 -C 6 alkyl)-1-(linear or branched C 1 -C 6 alkyl)pyrrolidinium, or 1-(linear or branched C 1 -C 6 alkyl)-1-(linear or branched C 1 -C 6 alkyl)piperidinium, tetra(linear or branched C 1 -C 6 alkyl)phosphonium, tri(C 5 -C 8 cycloalkyl)-(linear or branched C 1 -C 6 alkyl)phosphonium, tetra(linear or branched C 1 -C 6 )ammonium, or tri(C 5 -C 8 cycloalkyl)-(linear or branched C 1 -C 6 alkyl)ammonium.
  12. 12 . The electrochromic device of claim 1 , wherein said polymer matrix comprises a further polymer, wherein said further polymer comprises at least one of poly((meth)acrylonitrile), poly(vinylidene fluoride), poly(vinylidene fluoride-co-perfluoro(linear or branched C 1 -C 6 alkylene)), or poly((linear or branched C 1 -C 8 alkyl)(meth)acrylate).
  13. 13 . An electrochromic device comprising: (a) a first substrate having a surface comprising a first transparent electrode layer; (b) a second substrate having a surface comprising a second transparent conductive electrode layer, wherein said first transparent electrode layer and said second transparent electrode layer are in opposing spaced opposition; and (c) an electrochromic layer interposed between said first transparent electrically conductive electrode layer and said second transparent electrically conductive electrode layer, wherein said electrochromic layer comprises, (i) an electrochromic material comprising a cathodic component having cationic charge, wherein said cathodic component further comprises counter-anions, wherein each counter-anion of said cathodic component is an anodic component having an anion covalently bonded thereto, (ii) an optional electrolyte, and (iii) a polymer matrix, wherein said polymer matrix comprises a polymer, wherein said polymer comprises residues of a monomer represented by the following Formula (I), wherein for Formula (I), R 1 is in each case independently hydrogen or methyl, R 2 is in each case independently a single bond, a divalent linear or branched alkane, or divalent linear or branched cycloalkane, Y + is in each case independently represented by one of the following Formulas (A), (B), (C), (D), (E), (F), and (G), wherein independently for each of Formulas (A), (B), (C), (D), (E), (F), and (G), R 3 , R 4 , and R 5 are in each case independently selected from linear or branched alkyl or cycloalkyl, and X − is represented by the following Formula (II), wherein for Formula (II), R 6 and R 7 are each independently selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, wherein said anodic component having an anion covalently bonded thereto comprises an anodic component represented by the following Formula (IV), and optionally an anodic component represented by the following Formula (III), wherein for Formula (IV), R 9 is selected from divalent linear or branched alkane linking group, and R 10 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and wherein for Formula (III), R 8 is selected from divalent linear or branched alkane linking group.
  14. 14 . The electrochromic device of claim 13 , wherein said cathodic component comprises at least one of a 1,1′-disubstituted-4,4′-dipyridinium cation represented by the following Formula (V), or a 1,1-(alkane-alpha, omega-diyl)-bis-(1′-substituted-4,4′-dipyridinium) cation represented by the following Formula (VI), wherein for Formula (V), R 11 and R 12 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cyloalkyl, unsubstituted aryl, and substituted aryl, and for Formula (VI), R 13 and R 15 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cyloalkyl, unsubstituted aryl, and substituted aryl, and R 14 is selected from divalent linear or branched C 1 -C 10 alkane linking group.
  15. 15 . An electrochromic device comprising: (a) a first substrate having a surface comprising a first transparent electrode layer; (b) a second substrate having a surface comprising a second transparent conductive electrode layer, wherein said first transparent electrode layer and said second transparent electrode layer are in opposing spaced opposition; and (c) an electrochromic layer interposed between said first transparent electrically conductive electrode layer and said second transparent electrically conductive electrode layer, wherein said electrochromic layer comprises, (i) a cathodic component, (ii) an anodic component, (iii) an optional electrolyte, and (iv) a polymer matrix, wherein said polymer matrix comprises a polymer, wherein said polymer comprises residues of a monomer represented by the following Formula (I), wherein for Formula (I), R 1 is in each case independently hydrogen or methyl, R 2 is in each case independently a single bond, a divalent linear or branched alkane, or divalent linear or branched cycloalkane, Y + is in each case independently represented by one of the following Formulas (A), (B), (C), (D), (E), (F), and (G), wherein independently for each of Formulas (A), (B), (C), (D), (E), (F), and (G), R 3 , R 4 , and R 5 are in each case independently selected from linear or branched alkyl or cycloalkyl, and X − is represented by the following Formula (II), wherein for Formula (II), R 6 and R 7 are each independently selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and wherein said cathodic component comprises a cathodic component having cationic charge selected from at least one of a 1,1′-disubstituted-4,4′-dipyridinium cation represented by the following Formula (V), or a 1,1-(alkane-alpha, omega-diyl)-bis-(1′-substituted-4,4′-dipyridinium) cation represented by the following Formula (VI), wherein for Formula (V) and Formula (VI), R 11 , R 12 , R 13 , and R 15 are in each case independently selected from linear or branched alkyl, unsubstituted cycloalkyl, substituted cycloalkyl, unsubstituted aryl, substituted aryl, a group represented by the following Formula (VII), a group represented by the following Formula (VIII), wherein for Formula (VII) and Formula (VIII), R 16 and R 17 are in each case independently selected from divalent linear or branched alkane linking group, and for Formula (VIII), R 18 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and for Formula (VI), R 14 is selected from divalent linear or branched alkane linking group, provided that for Formula (V), at least one of R 1 and R 12 is independently selected from said group represented by Formula (VIII), and provided that for Formula (VI), at least one of R 13 and R 15 is independently selected from said group represented by Formula (VIII).
  16. 16 . An electrochromic composition comprising: (i) a cathodic component, (ii) an anodic component, (iii) an optional electrolyte, (iv) at least one of, (a) a polymeric thickener, or (b) a polymerizable monomer composition, and (v) a solvent, wherein said polymeric thickener comprises a polymer, wherein said polymer comprises residues of a monomer represented by the following Formula (I), and wherein said polymerizable monomer composition independently comprises said monomer represented by the following Formula (I), wherein for Formula (I), R 1 is in each case independently hydrogen or methyl, R 2 is in each case independently a single bond, a divalent linear or branched alkane, or divalent linear or branched cycloalkane, Y + is in each case independently represented by one of the following Formulas (A), (B), (C), (D), (E), (F), and (G), wherein independently for each of Formulas (A), (B), (C), (D), (E), (F), and (G), R 3 , R 4 , and R 5 are in each case independently selected from linear or branched alkyl or cycloalkyl, and X − is represented by the following Formula (II), wherein for Formula (II), R 6 and R 7 are each independently selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, wherein said anodic component comprises an anodic component represented by the following Formula (IV), and optionally an anodic component represented by the following Formula (III), wherein for Formula (IV), R 9 is selected from divalent linear or branched alkane linking group, and R 10 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and wherein for Formula (III), R 8 is selected from divalent linear or branched alkane linking group.
  17. 17 . The electrochromic composition of claim 16 , wherein said solvent comprises at least one of ethylene carbonate, propylene carbonate, gamma-butyrolactone, gamma-valerolactone, N-methylpyrrolidone, polyethylene glycol, carboxylic acid esters of polyethylene glycol, sulfolane, alpha, omega-(C 2 -C 8 )dinitriles, or di(linear or branched C 1 -C 8 )acetamides.
  18. 18 . The electrochromic composition of claim 16 , wherein said anodic component further comprises a counter-cation.
  19. 19 . The electrochromic composition of claim 18 , wherein each counter-cation is independently selected from tetra(linear or branched alkyl) ammonium cation.
  20. 20 . The electrochromic composition of claim 16 , said cathodic component comprises at least one of a 1,1′-disubstituted-4,4′-dipyridinium cation represented by the following Formula (V), or a 1,1-(alkane-alpha, omega-diyl)-bis-(1′-substituted-4,4′-dipyridinium) cation represented by the following Formula (VI), wherein for Formula (V), R 11 and R 12 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cyloalkyl, unsubstituted aryl, and substituted aryl, and for Formula (VI), R 13 and R 15 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cyloalkyl, unsubstituted aryl, and substituted aryl, and R 14 is selected from divalent linear or branched C 1 -C 10 alkane linking group.

Description

CROSS-REFERENCE TO RELATED APPLICATION This application is entitled to and claims priority to U.S. Provisional Patent Application No. 63/333,255, which was filed on Apr. 21, 2022, the disclosure of which is incorporated herein by reference in its entirety. FIELD The present invention relates to electrochromic devices and compositions that include a polymer that includes residues of, or a polymerizable composition that includes, ((meth)acrylate-amine cation bis(substituted-sulfonyl)imide anion)) monomer. BACKGROUND Electrochromism involves a reversible change in a material's visible color and/or transmittance of visible light with the application of an electrical potential. The change in color and/or transmittance typically involves alternately cycled oxidized and reduced charge states. Generally, a material that generates a color while undergoing reduction is referred to as a cathodically-coloring electrochromic material; and a material that generates color while undergoing oxidation is referred to as an anodically-coloring electrochromic material. Electrochromic devices typically include an electrochromic layer that is interposed between the separate and opposed transparent electrode layers of separate and opposed substrates. The electrochromic layer typically includes a polymer matrix through which cathodic and anodic components thereof are transported towards their respective cathode and anode where reduction and oxidation reactions correspondingly occur, at least one of which results in a change in color of and/or transmittance of visible light through the electrochromic device. The kinetics of electrochromic devices is typically governed primarily by mass transport of cathodic components and anodic components across and through the electrochromic layer. For purposes of charge conversion, the electrical currents of both electrodes (cathode and anode) are necessarily equal. If one of the components (cathodic or anodic component) moves or is transported more slowly through or across the electrochromic layer, typically a higher concentration of that component is required, and more particularly, a higher concentration gradient of the slower moving/transported component at the electrode interface (a higher interfacial concentration) is required to equalize the diffusion flux and maintain a given current. Adjusting and/or maintaining a higher concentration of the component having reduced mass transport can require additional preparation and/or manufacturing steps, and can result in inadvertent formulation errors. Mass transport imbalances can, in some instances, result in reduced durability of the electrochromic device, in particular if the slower mass transported active component is subject to over-oxidization or over-reduction at a particular electrode. The polymer matrix of the electrochromic layer typically includes a polymer. The polymer of the polymer matrix can have a significant influence on the transport properties of the cathodic and anodic components there-through. In addition, the polymer of the polymer matrix can affect the adhesive properties of the electrochromic layer. Poor adhesive properties can result in undesirable separation and/or delamination of the transparent electrode layers and related substrates from the electrochromic layer. The polymer of the electrochromic layer can also affect the transparency of the electrochromic device. In some instances, poor solubility of components within the polymer of the electrochromic layer can result in an undesirable increase in haze, which correspondingly and adversely affects the transparency of the electrochromic device. The polymer can affect the durability and high-temperature performance of the electrochromic layer. For example, degradation of the polymer over time can result in an undesirable reduction in the durability and high-temperature performance of the electrochromic layer and correspondingly the electrochromic device. It would be desirable to develop new polymers for use in forming the polymer matrix of the electrochromic layer of electrochromic devices. It would be further desirable that such newly developed polymers provide properties that are at least as good as and preferably better than those of existing polymers, such as, but not limited to, balanced mass transport properties, reduced haze, reduced or low current densities, improved high temperature performance, and/or improved adhesive properties. SUMMARY In accordance with the present invention, there is provided an electrochromic device comprising: (a) a first substrate having a surface comprising a first transparent electrode layer; (b) a second substrate having a surface comprising a second transparent conductive electrode layer, wherein the first transparent electrode layer and the second transparent electrode layer are in opposing spaced opposition; and (c) an electrochromic layer interposed between the first transparent electrically conductive electrode layer and the sec