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US-12618003-B2 - Electrochromic devices and compositions including poly((diallyldimethylammonium bis (substituted-sulfonyl)imide anion))

US12618003B2US 12618003 B2US12618003 B2US 12618003B2US-12618003-B2

Abstract

The present invention relates to electrochromic devices and compositions, that include a polymer matrix or thickener, that includes poly((diallyldimethylammonium bis(substituted-sulfonyl)imide X − )) polymer, where each X − independently is an anion represented by the following Formula (A), With reference to Formula (A), R 9 and R 10 are each independently selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl.

Inventors

  • Ivan Alexandrovich Sokol
  • DYLAN THOMAS CHRISTIANSEN

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; (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 poly(diallyldimethylammonium X − ), wherein each X − independently is an anion represented by the following Formula (A), wherein R 9 and R 10 are each independently selected from the group consisting of fluorine, linear or branched fluorinated alkyl, and linear or branched perfluorinated alkyl, wherein said anodic component comprises an anodic component anion represented by the following Formula (II), and optionally an anodic component anion represented by the following Formula (I), wherein for Formula (II), R 2 is selected from divalent linear or branched alkane linking group, and R 3 is selected from the group consisting of fluorine, linear or branched fluorinated alkyl, and linear or branched perfluorinated alkyl, and wherein for Formula (I), R 1 is selected from divalent linear or branched alkane linking group.
  2. 2 . The electrochromic device of claim 1 , wherein for Formula (A), R 9 and R 10 are each independently selected from the group consisting of fluorine, linear or branched C 1 -C 10 fluorinated alkyl, and linear or branched C 1 -C 10 perfluorinated alkyl.
  3. 3 . The electrochromic device of claim 2 , wherein for Formula (A), R 9 and R 10 are each independently selected from linear or branched C 1 -C 5 perfluorinated alkyl.
  4. 4 . The electrochromic device of claim 3 , wherein for Formula (A), R 9 and R 10 are each trifluoromethyl, and said polymer of said polymer matrix comprises poly((diallyldimethylammonium) bis(trifluoromethane)sulfonimide)).
  5. 5 . The electrochromic device of claim 1 , wherein for Formula (I), R 1 is selected from divalent linear or branched C 1 -C 10 alkane linking group, and for Formula (II), R 2 is selected from divalent linear or branched C 1 -C 10 alkane linking group, and R 3 is selected from the group consisting of fluorine, linear or branched C 1 -C 10 fluorinated alkyl, and linear or branched C 1 -C 10 perfluorinated alkyl.
  6. 6 . The electrochromic device of claim 5 , wherein for Formula (I), R 1 is selected from divalent linear or branched C 1 -C 5 alkane linking group, and for Formula (II), R 2 is selected from divalent linear or branched C 1 -C 5 alkane linking group, and R 3 is selected from linear or branched C 1 -C 5 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 8 , wherein each counter-cation is independently selected from tetra(linear or branched C 1 -C 10 alkyl) ammonium cation.
  10. 10 . The electrochromic device of claim 1 , said cathodic component comprises at least one of a 1,1′-disubstituted-4,4′-dipyridinium cation represented by the following Formula (III), or a 1,1-(alkane-alpha, omega-diyl)-bis-(1′-substituted-4,4′-dipyridinium) cation represented by the following Formula (VI), wherein for Formula (III), R 4 and R 5 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cycloalkyl, unsubstituted aryl, and substituted aryl, and for Formula (IV), R 6 and R 8 are each independently selected from linear or branched C 1 -C 1 o alkyl, unsubstituted C 3 -C 7 cycloalkyl, substituted C 3 -C 7 cycloalkyl, unsubstituted aryl, and substituted aryl, and R 7 is selected from divalent linear or branched C 1 -C 10 alkane linking group.
  11. 11 . The electrochromic device of claim 10 , wherein for Formula (III) R 4 and R 5 are each independently selected from linear or branched C 1 -C 4 alkyl, unsubstituted phenyl, and substituted phenyl, and for Formula (IV) R 6 and R 8 are each independently selected from linear or branched C 1 -C 4 alkyl, unsubstituted phenyl, and substituted phenyl, and R 7 is selected from divalent linear or branched C 1 -C 8 alkane linking group.
  12. 12 . The electrochromic device of claim 10 , 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 − .
  13. 13 . 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 the group consisting of 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)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, and tri(C 5 -C 8 cycloalkyl)-(linear or branched C 1 -C 6 alkyl)ammonium.
  14. 14 . 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).
  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) 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 poly(diallyldimethylammonium X − ), wherein each X − independently is an anion r wherein R 9 and R 10 are each independently selected from the group consisting of fluorine, linear or branched fluorinated alkyl, and linear or branched perfluorinated alkyl, wherein said anodic component having an anion covalently bonded thereto comprises an anodic component anion represented by the following Formula (II), and optionally an anodic component anion represented by the following Formula (I), wherein for Formula (II), R 2 is selected from divalent linear or branched alkane linking group, and R 3 is selected from the group consisting of fluorine, linear or branched fluorinated alkyl, and linear or branched perfluorinated alkyl, and wherein for Formula (I), R 1 is selected from divalent linear or branched alkane linking group.
  16. 16 . The electrochromic device of claim 15 , wherein for Formula (A), R 9 and R 10 are each independently selected from the group consisting of fluorine, linear or branched C 1 -C 10 fluorinated alkyl, and linear or branched C 1 -C 1 o perfluorinated alkyl.
  17. 17 . The electrochromic device of claim 16 , wherein for Formula (A), R 9 and R 10 are each independently selected from linear or branched C 1 -C 5 perfluorinated alkyl.
  18. 18 . The electrochromic device of claim 17 , wherein for Formula (A), R 9 and R 10 are each trifluoromethyl, and said polymer of said polymer matrix comprises poly((diallyldimethylammonium) bis(trifluoromethane)sulfonimide).
  19. 19 . The electrochromic device of claim 15 , wherein said cathodic component having cationic charge and said anodic component having said anion covalently bonded thereto, together have a net neutral charge.
  20. 20 . The electrochromic device of claim 15 , wherein for Formula (I), R 1 is selected from divalent linear or branched C 1 -C 10 alkane linking group, and for Formula (II), R 2 is selected from divalent linear or branched C 1 -C 10 alkane linking group, and R 3 is selected from the group consisting of fluorine, linear or branched C 1 -C 10 fluorinated alkyl, and linear or branched C 1 -C 10 perfluorinated alkyl.

Description

CROSS-REFERENCE TO RELATED APPLICATION This application is entitled to and claims priority to U.S. Provisional Patent Application No. 63/333,219, 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 matrix or thickener, that includes poly((diallyldimethylammonium bis(substituted-sulfonyl)imide anion)) as a polymer. 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 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 conductiv