Electrochromic thermoplastics, devices, and composites

Patent metadata

Field	Value
Publication number	US-2016377946-A1
Application number	US-201615065730-A
Country	US
Kind code	A1
Filing date	Mar 9, 2016
Priority date	Jun 25, 2015
Publication date	Dec 29, 2016
Grant date	—

Abstract

An electrochromic thermoplastic composition includes about 10 wt % to about 60 wt % a poly(vinyl alcohol), a poly(acrylic acid), a poly(acrylic acid) salt, a polyaniline salt, a poly(diallyl dimethyl ammonium chloride), a poly(ethylene-co-acrylic acid), a co-polymer of any two or more thereof, or a mixture of any two or more thereof; about 40 wt % to about 90 wt % of a protic solvent; and at least one electroactive material; wherein the composition does not include lithium chloride, tetrabutylammonium bromide, lithium bis(trifluoromethanesulfonyl)imide, lithium triflate, and lithium hexafluorophosphate.

First claim

What is claimed is:

1 . An electrochromic thermoplastic composition comprising:
about 10 wt % to about 60 wt % of a poly(vinyl alcohol), a poly(acrylic acid), a poly(acrylic acid) salt, a polyaniline salt, a poly(diallyl dimethyl ammonium chloride), a poly(ethylene-co-acrylic acid), a co-polymer of any two or more thereof, or a mixture of any two or more thereof; about 40 wt % to about 90 wt % of a protic solvent; and at least one electroactive material; wherein the composition is substantially void of lithium chloride, tetrabutylammonium bromide, lithium bis(trifluoromethanesulfonyl)imide, lithium triflate, and lithium hexafluorophosphate.

2 . The electrochromic thermoplastic composition of claim 1 comprising:
about 10 wt % to about 60 wt % poly(vinyl alcohol),
about 40 wt % to about 90 wt % of the protic solvent; and
at least one electroactive material.

3 . The electrochromic thermoplastic composition of claim 1 , wherein the protic solvent comprises an alcohol, a carboxylic acid, a primary amino compound, a secondary amino compound, water, or a mixture of any two or more thereof.

4 . The electrochromic thermoplastic composition of claim 1 , wherein the at least one electroactive material comprises a viologen represented by Formula (I):

wherein:
R 1 and R 2 are each independently an alkyl group substituted with a carboxylate, phosphonate, phosphate, or sulfonate;
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each independently H, OR 11 , F, Cl, Br, I, CN, NO 2 , alkyl, or aryl; and
R 11 is H or alkyl.

5 . The electrochromic thermoplastic composition of claim 1 , wherein the at least one electroactive material comprises an anodic material comprising a compound represented by Formula (II)

wherein:
R 12 and R 21 are each independently an alkyl group substituted with a carboxylate, phosphonate, phosphate, or sulfonate;
R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 are each independently H, F, Cl, Br, I, CN, OR 22 , SR 22 , NO 2 , alkyl, aryl, or amino, or any two adjacent R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 join to form a monocyclic, polycyclic, or heterocyclic group;
each R 22 is independently at each occurrence H or alkyl; and
A is a cation.

6 . The electrochromic thermoplastic composition of claim 5 which comprises at least two different compounds represented by Formula (II).

7 . The electrochromic thermoplastic composition of claim 1 , wherein the composition comprises at least one cathodic material and at least one anodic material.

8 . An electrochromic thermoplastic composition comprising
about 10 wt % to about 60 wt % poly(vinyl alcohol); about 40 wt % to about 90 wt % of a mixture comprising water and at least one protic solvent; and at least one electroactive material.

9 . The electrochromic thermoplastic composition of claim 8 , wherein the at least one electroactive material comprises a viologen represented by Formula (I):

wherein:
R 1 and R 2 are each independently an alkyl group substituted with a carboxylate, phosphonate, phosphate, or sulfonate;

R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each independently H, OR 11 , F, Cl, Br, I, CN, NO 2 , alkyl, or aryl; and
R 11 is independently at each occurrence H or alkyl.

10 . The electrochromic thermoplastic composition of claim 8 , wherein the at least one electroactive material comprises an anodic material represented by Formula (II):

wherein:
R 12 and R 21 are each independently an alkyl group substituted with a carboxylate, phosphonate, phosphate, or sulfonate;
R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 are each independently H, F, Cl, Br, I, CN, OR 22 , SR 22 , NO 2 , alkyl, aryl, or amino, or any two adjacent R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 join to form a monocyclic, polycyclic, or heterocyclic group;
each R 22 is independently at each occurrence H or alkyl; and
A is a cation.

11 . The electrochromic thermoplastic composition of claim 8 which is void of lithium chloride, tetrabutylammonium bromide, lithium bis(trifluoromethanesulfonyl)imide, lithium triflate, and lithium hexafluorophosphate.

12 . An electrochromic thermoplastic composition comprising:
about 10 wt % to about 35 wt % poly(vinyl formal), about 10 wt % to about 50 wt % poly(methyl methacrylate), or about 10 wt % to about 50 wt % poly(ethylene-co-vinyl acetate); about 50 wt % to about 90 wt % of an aprotic solvent; and at least one electroactive material.

13 . The electrochromic thermoplastic composition of claim 12 comprising:
about 10 wt % to about 35 wt % poly(vinyl formal) or about 10 wt % to about 50 wt % poly(methyl methacrylate);
about 50 wt % to about 90 wt % of an aprotic solvent; and
at least one electroactive material.

14 . An electrochromic composite comprising:
a first electrochromic thermoplastic composition of claim 1 comprising a cathodic material, a front surface, and a rear surface; a second electrochromic thermoplastic composition of claim 1 comprising an anodic material, a front surface, and a rear surface; a layer comprising:
about 10 wt % to about 60 wt % poly(vinyl alcohol);
about 40 wt % to about 90 wt % of a solvent comprising a protic solvent;
a front surface; and
a rear surface;
wherein
the front surface of the layer is annealed to the rear surface of the first electrochromic thermoplastic composition; and
the rear surface of the layer is annealed to the front surface of the second electrochromic thermoplastic composition.

15 . The electrochromic composite of claim 14 , wherein the layer further comprises an electrolyte salt.

16 . An electrochromic composite comprising:
a first electrochromic thermoplastic composition of claim 8 comprising a cathodic material, a front surface, and a rear surface; a second electrochromic thermoplastic composition of claim 8 comprising an anodic material, a front surface, and a rear surface; a layer comprising:
about 10 wt % to about 60 wt % poly(vinyl alcohol);
about 40 wt % to about 90 wt % of a solvent comprising a protic solvent;
a front surface; and
a rear surface;
wherein
the front surface of the layer is annealed to the rear surface of the first electrochromic thermoplastic composition; and
the rear surface of the layer is annealed to the front surface of the second electrochromic thermoplastic composition.

17 . The electrochromic composite of claim 16 , wherein the layer further comprises an electrolyte salt.

18 . An electrochromic device comprising
an electrochromic thermoplastic of claim 1 comprising a front surface and a rear surface; a first substrate with a first conductive surface; and a second substrate with a second conductive surface; wherein the first conductive surface is annealed to the front surface of the electrochromic thermoplastic and the second conductive surface is annealed to the rear surface of the electrochromic thermoplastic.

19 . An electrochromic device comprising
an electrochromic thermoplastic of claim 8 comprisin

Assignees

• Gentex Corp

Inventors

• Baumann Kelvin L

Classifications

• C08K5/3465 Primary

  condensed with carbocyclic rings · CPC title

• G02F1/15165

  Polymers · CPC title

• C08K5/3432

  Six-membered rings · CPC title

• G02F2001/15145

  the electrochromic layer comprises a mixture of anodic and cathodic compounds · CPC title

• C08K2201/019

  the composition being defined by the absence of a certain additive · CPC title