US 12,619,116 B2Granted

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

AssigneeVitro Flat Glass LLC

InventorsDylan Thomas Christiansen, Ivan Alexandrovich Sokol

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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): R1 is in each case independently hydrogen or methyl; R2 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(R3)(R4)(R5)+; and X− is a bis(substituted-sulfonyl)imide anion represented by the following Formula (II),

Claims24

Dependent claims

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),
R1 is in each case independently hydrogen or methyl,
R2 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), R3, R4, and R5 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), R6 and R7 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), R9 is selected from divalent linear or branched alkane linking group, and R10 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and
wherein for Formula (III), R8 is selected from divalent linear or branched alkane linking group.

17 more elements

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),
R1 is in each case independently hydrogen or methyl,
R2 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), R3, R4, and R5 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), R6 and R7 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), R9 is selected from divalent linear or branched alkane linking group, and R10 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and
wherein for Formula (III), R8 is selected from divalent linear or branched alkane linking group.

15 more elements

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),
R1 is in each case independently hydrogen or methyl,
R2 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), R3, R4, and R5 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), R6 and R7 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), R11, R12, R13, and R15 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), R16 and R17 are in each case independently selected from divalent linear or branched alkane linking group, and for Formula (VIII), R18 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and
for Formula (VI), R14 is selected from divalent linear or branched alkane linking group,
provided that for Formula (V), at least one of R1 and R12 is independently selected from said group represented by Formula (VIII), and
provided that for Formula (VI), at least one of R13 and R15 is independently selected from said group represented by Formula (VIII).

20 more elements

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),
R1 is in each case independently hydrogen or methyl,
R2 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), R3, R4, and R5 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), R6 and R7 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), R9 is selected from divalent linear or branched alkane linking group, and R10 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and
wherein for Formula (III), R8 is selected from divalent linear or branched alkane linking group.

15 more elements

An electrochromic composition comprising:

(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,
(iii) at least one of,
(a) a polymeric thickener, or
(b) a polymerizable monomer composition, and
(iv) 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),
R1 is in each case independently hydrogen or methyl,
R2 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), R3, R4, and R5 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), R6 and R7 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), R9 is selected from divalent linear or branched alkane linking group, and R10 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and
wherein for Formula (III), R8 is selected from divalent linear or branched alkane linking group.

14 more elements

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),
R1 is in each case independently hydrogen or methyl,
R2 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), R3, R4, and R5 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), R6 and R7 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), R11, R12, R13, and R15 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), R16 and R17 are in each case independently selected from divalent linear or branched alkane linking group, and for Formula (VIII), R18 is selected from fluorine, linear or branched fluorinated alkyl, or linear or branched perfluorinated alkyl, and
for Formula (VI), R14 is selected from divalent linear or branched alkane linking group,
provided that for Formula (V), at least one of R1 and R12 is independently selected from said group represented by Formula (VIII), and
provided that for Formula (VI), at least one of R13 and R15 is independently selected from said group represented by Formula (VIII).

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/133,045Filed 11 Apr 2023 · us provisional application
Priority: 21 Apr 2022
Published: US 2023/0341738 A126 Oct 2023
Granted: 5 May 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

G02F 1/15165
Comprising organic material: polymers
C09K 9/02
Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some…
G02F 1/1525
Comprising inorganic material: characterised by a particular ion transporting layer, e.g. electrolyte
G02F 1/155
Constructional details: electrodes