Anodic electroactive materials having a solublizing moiety

• US 6,496,294 B2
• Filed: 07/17/2001
• Issued: 12/17/2002
• Est. Priority Date: 12/03/1999
• Status: Expired due to Term

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Guarr, Thomas F., Lomprey, Jeffrey R.
• Primary Examiner(s): Dang, Hung Xuan
• Assistant Examiner(s): Tra, Tuyen
• Application Number:
  US09/907,047
• Publication Number:
  US 20020008897A1
• Time in Patent Office: 518 Days
• Field of Search: 359/265, 359/267, 359/270, 359/273, 252/582
• US Class Current: 359/265
• CPC Class Codes: C09K 9/00 Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
• CPC Class Codes: G02F 1/1503 caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
• CPC Class Codes: G02F 2001/15145 the electrochromic layer comprises a mixture of anodic and cathodic compounds

Abstract

Anodic electrochromic materials for use in an electrochromic device comprising a first moiety, wherein the first moiety comprises a metallocene or a substituted metallocene, and a second moiety, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in an associated solvent relative to solubility of the first moiety without the second moiety.

Claims

1. An electrochromic medium for use in an electrochromic device, comprising:

at least one solvent;

a cathodic electroactive material;

an anodic electroactive material which includes;

a first moiety having a solubility in the at least one solvent; and

a second moiety, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent relative to the first moiety without the second moiety; and

wherein at least one of the cathodic and anodic electroactive materials is electrochromic.

2. The electrochromic medium according to claim 1, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent by a factor of greater than approximately two relative to the first moiety without the second moiety.

3. The electrochromic medium according to claim 1, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent by more than approximately one order of magnitude relative to the first moiety without the second moiety.

4. The electrochromic medium according to claim 1, wherein the first moiety is selected from the group comprising ferrocene, substituted ferrocenes, and mixtures thereof.

5. The electrochromic medium according to claim 1, wherein the first moiety is represented by the formula:

wherein R₁-R₁₀ are the same or different and comprise H or a straight or branched alkyl group containing approximately 1 to approximately 10 carbon atoms and wherein at least one of R₁-R₁₀ is associated with the second moiety.

6. The electrochromic medium according to claim 5, wherein R₁-R₁₀ are the same or different and at least three of R₁-R₁₀ comprise a straight or branched alkyl group containing approximately 1 to approximately 40 carbon atoms, and wherein any remainder of R₁-R₁₀ comprise H.

7. The electrochromic medium according to claim 1, wherein the second moiety is selected from the group comprising nitrites, nitro constituents, sulfoxides, sulfonates, phosphonium constituents, phosphonates, phosphonites, ammonium constituents, viologens including bipyridinyl constituents, carbonyls including carbonates, carbamates, ketones, esters, and amides, ethers including polyethers, amines including tertiary amines, alkenes, alkynes, and mixtures thereof.

8. The electrochromic medium according to claim 1, wherein the second moiety is represented by at least one of the formulae:

wherein R₁₁-R₃₁ are the same or different and comprise H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing approximately 1 to approximately 10 carbon atoms;

wherein Ar is an aryl constituent including phenyl;

wherein m is an integer ranging from approximately 1 to approximately 5;

wherein n is an integer ranging from approximately 1 to approximately 20; and

wherein X is associated with the first moiety and is selected from the group comprising a direct bond, an alkyl, aryl, alkaryl, aralkyl, ether, or polyether chain containing approximately 1 to approximately 40 carbon atoms, a silyl or siloxyl chain containing approximately 1 to approximately 40 silicon atoms, and mixtures thereof.

9. The electrochromic medium according to claim 1, wherein the second moiety is represented by the formula:

10. The electrochromic medium according to claim 1, wherein the at least one solvent is selected from the group comprising 3-methylsulfolane, glutaronitrile, dimethyl sulfoxide, dimethyl formamide, acetonitrile, polyethers including tetraglyme, alcohols including ethoxyethanol, nitrites including 3-hydroxypropionitrile, 2-methylglutaronitrile, ketones including 2-acetylbutyrolactone, cyclopentanone, cyclic esters including beta-propiolactone, gamma-butyrolactone, gamma-valerolactone, propylene carbonate, ethylene carbonate and homogenous mixtures of the same.

11. The electrochromic medium according to claim 1, wherein the concentration of the anodic material ranges from approximately 1 mM to approximately 1000 mM.

12. The electrochromic medium according to claim 11, wherein the concentration of the anodic material ranges from approximately 5 mM to approximately 500 mM.

13. An electrochromic medium for use in an electrochromic device, comprising:

at least one solvent, wherein the at least one solvent is selected from the group comprising 3-methylsulfolane, glutaronitrile, dimethyl sulfoxide, dimethyl formamide, acetonitrile, polyethers including tetraglyme, alcohols including ethoxyethanol, nitriles including 3-hydroxypropionitrile, 2-methylglutaronitrile, ketones including 2-acetylbutyrolactone, cyclopentanone, cyclic esters including beta-propiolactone, gamma-butyrolactone, gamma-valerolactone, propylene carbonate, ethylene carbonate and homogenous mixtures of the same;

a cathodic electroactive material;

an anodic electroactive material which includes;

a first moiety having a solubility in the at least one solvent, wherein the first moiety is selected from the group comprising ferrocene, substituted ferrocenes, and mixtures thereof; and

a second moiety, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent relative to the first moiety without the second moiety, and wherein the second moiety is selected from the group comprising nitriles, nitro constituents, sulfoxides, sulfonates, phosphonium constituents, phosphonates, phosphonites, ammonium constituents, viologens including bipyridinyl constituents, carbonyls including carbonates, carbamates, ketones, esters, and amides, ethers including polyethers, amines including tertiary amines, alkenes, alkynes, and mixtures thereof; and

wherein at least one of the cathodic and anodic electroactive materials is electrochromic.

14. An electrochromic medium for use in an electrochromic device, comprising:

at least one solvent, wherein the at least one solvent is selected from the group comprising 3-methylsulfolane, glutaronitrile, dimethyl sulfoxide, dimethyl formamide, acetonitrile, polyethers including tetraglyme, alcohols including ethoxyethanol, nitriles including 3-hydroxypropionitrile, 2-methylglutaronitrile, ketones including 2-acetylbutyrolactone, cyclopentanone, cyclic esters including beta-propiolactone, gamma-butyrolactone, gamma-valerolactone, propylene carbonate, ethylene carbonate and homogenous mixtures of the same;

a cathodic electroactive material;

an anodic electroactive material which includes;

a first moiety having a solubility in the at least one solvent, wherein the first moiety is represented by the formula;

 

wherein R₁-R₁₀ are the same or different and comprise H or a straight or branched alkyl group containing approximately 1 to approximately 10 carbon atoms and wherein at least one of R₁-R₁₀ is associated with the second moiety; and

a second moiety, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent relative to the first moiety without the second moiety, and wherein the second moiety is represented by at least one of the formulae;

 

wherein R₁₁-R₃₁ are the same or different and comprise H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing approximately 1 to approximately 10 carbon atoms;

wherein Ar is an aryl constituent including phenyl;

wherein m is an integer ranging from approximately 1 to approximately 5;

wherein n is an integer ranging from approximately 1 to approximately 20; and

wherein X is associated with the first moiety and is selected from the group comprising a direct bond, an alkyl, aryl, alkaryl, aralkyl, ether, or polyether chain containing approximately 1 to approximately 40 carbon atoms, a silyl or siloxyl chain containing approximately 1 to approximately 40 silicon atoms, and mixtures thereof;

or wherein the second moiety is represented by the formula;

15. An electrochromic device, comprising:

a first substantially transparent substrate having an electrically conductive material associated therewith;

a second substrate having an electrically conductive material associated therewith;

an electrochromic medium contained within a chamber positioned between the first and second substrates which comprises;

at least one solvent;

a cathodic electroactive material;

an anodic electroactive material which includes;

a first moiety having a solubility in the at least one solvent; and

a second moiety, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent relative to the first moiety without the second moiety; and

wherein at least one of the cathodic and anodic electroactive materials is electrochromic.

16. The electrochromic device according to claim 15, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent by a factor of greater than approximately two relative to the first moiety without the second moiety.

17. The electrochromic device according to claim 15, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent by more than approximately one order of magnitude relative to the first moiety without the second moiety.

18. An anodic electrochromic material for use in an electrochromic device, comprising:

a first moiety having a solubility in at least one associated solvent; and

a second moiety, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent relative to the first moiety without the second moiety.

19. The electrochromic medium according to claim 18, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent by a factor of greater than approximately two relative to the first moiety without the second moiety.

20. The electrochromic medium according to claim 18, wherein the second moiety comprises at least one constituent which serves to increase the solubility of the first moiety in the at least one solvent by more than approximately one order of magnitude relative to the first moiety without the second moiety.