Electrochromic devices and compositions including anodic components as cathodic component counter-anions

Patent metadata

Field	Value
Publication number	US-12584064-B2
Application number	US-202318134057-A
Country	US
Kind code	B2
Filing date	Apr 13, 2023
Priority date	Apr 21, 2022
Publication date	Mar 24, 2026
Grant date	Mar 24, 2026

Abstract

The present invention relates to electrochromic devices and compositions, in which the cathodic component has cationic charge and includes counter-anions, where each counter-anion of the cathodic component is an anodic component having an anion covalently bonded thereto.

First claim

What is claimed is:

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) 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 anodic component having an anion covalently bonded thereto is selected from an anodic component represented by at least one of the following Formula (I) or Formula (II),

wherein for Formula (I), R 1 is selected from divalent linear or branched alkane linking group, and
for Formula (II), R 2 is selected from divalent linear or branched alkane linking group, and R 3 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl.

2 . The electrochromic device of claim 1 , wherein said cathodic component having cationic charge and said anodic component having said anion covalently bonded thereto, together have a net neutral charge.

3 . 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 fluorine, linear or branched C 1 -C 10 fluorinated alkyl, or linear or branched C 1 -C 10 perfluorinated alkyl.

4 . The electrochromic device of claim 3 , 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 alkyl, and R 3 is selected from linear or branched C 1 -C 5 perfluorinated alkyl.

5 . 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 (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 10 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.

6 . The electrochromic device of claim 5 , 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.

7 . 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, 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.

8 . The electrochromic device of claim 1 , wherein said polymer matrix comprises a polymer, wherein said 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).

9 . An electrochromic composition comprising,
(i) 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, (iii) a polymeric thickener, and (iv) a solvent, wherein said anodic component having an anion covalently bonded thereto is selected from an anodic component represented by at least one of the following Formula (I) or Formula (II),

wherein for Formula (I), R 1 is selected from divalent linear or branched alkane linking group, and
for Formula (II), R 2 is selected from divalent linear or branched alkane linking group, and R 3 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl.

10 . The electrochromic composition of claim 9 , wherein said cathodic component having cationic charge and said anodic component having said anion covalently bonded thereto, together have a net neutral charge.

11 . The electrochromic composition of claim 9 , 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 fluorine, linear or branched C 1 -C 10 fluorinated alkyl, or linear or branched C 1 -C 10 perfluorinated alkyl.

12 . The electrochromic composition of claim 11 , 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 alkyl, and R 3 is selected from linear or branched C 1 -C 5 perfluorinated alkyl.

13 . The electrochromic composition of claim 9 , wherein 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, a

Assignees

• Vitro Flat Glass Llc

Inventors

• Christiansen Dylan Thomas
• Sokol Ivan Alexandrovich

Classifications

• G02F1/155

  Electrodes · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• G02F1/15165

  Polymers · CPC title

• G02F2001/164

  the electrolyte is made of polymers · CPC title

• C07D279/22

  with carbon atoms directly attached to the ring nitrogen atom · CPC title