Ultraviolet stabilizing materials having a solublizing moiety

• US 6,614,578 B2
• Filed: 08/02/2002
• Issued: 09/02/2003
• Est. Priority Date: 12/03/1999
• Status: Expired due to Term

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Kloeppner, Leroy J., Guarr, Thomas F., Giri, Punam, Baumann, Kelvin L., Lomprey, Jeffrey R.
• Primary Examiner(s): Dang, Hung Xuan
• Assistant Examiner(s): TRA, TUYEN Q
• Application Number:
  US10/211,485
• Publication Number:
  US 20030030883A1
• Time in Patent Office: 396 Days
• Field of Search: 359/265, 359/266-275, 252/582, 252/583, 252/586, 546/257
• 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 1/15165 Polymers
• CPC Class Codes: G02F 2001/15145 the electrochromic layer comprises a mixture of anodic and cathodic compounds

Abstract

The present invention is directed to an electrochromic medium for use in an electrochromic device comprising at least one solvent, an anodic material, a cathodic material, wherein both of the anodic and cathodic materials are electroactive and at least one of the anodic and cathodic materials is electrochromic, and an ultraviolet stabilizing material, wherein the ultraviolet stabilizing material includes a solublizing moiety which serves to increase solubility of the ultraviolet stabilizing material relative to the same without the solublizing moiety.

Claims

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

at least one solvent;

an anodic material;

a cathodic material, wherein both of the anodic and cathodic materials are electroactive and at least one of the anodic and cathodic materials is electrochromic; and

an ultraviolet stabilizing material, wherein the ultraviolet stabilizing material includes a solubilizing moiety which serves to increase solubility of the ultraviolet stabilizing material relative to the same without the solubilizing moiety.

2. The electrochromic medium according to claim 1, wherein the ultraviolet stabilizing material is represented by the formula:

wherein R₁ is OH;

wherein R₂-R₉ are the same or different and comprise H, OH, a halide, or a straight or branched alkyl, aryl, alkaryl, arakyl, alkoxy, or carboxy group containing 1 to approximately 20 carbon atoms; and

wherein at least one of R₂-R₉ is associated with a solubilizing moiety.

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

wherein R₁₀-R₂₆ are the same or different and comprise H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing 1 to approximately 10 carbon atoms;

wherein m is an integer ranging from 1 to approximately 10;

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

wherein X is associated with the ultraviolet stabilizing material 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, one or more of structures I-X, and mixtures thereof.

4. The electrochromic medium according to claim 1, wherein the solubilizing moiety is represented by the following formula:

wherein R₂₄ comprises H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing 1 to approximately 10 carbon atoms;

wherein m is an integer ranging from 1 to approximately 10;

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

wherein X is associated with the ultraviolet stabilizing material 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.

5. The electrochromic medium according to claim 1, wherein the ultraviolet stabilizing material is selected from at least one of the group consisting of TP1, TP2, TP3, TPEG, and mixtures thereof.

6. 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.

7. The electrochromic medium according to claim 1, wherein said electrochromic medium comprises a viscosity modifier.

8. The electrochromic medium according to claim 1, wherein said electrochromic medium comprises a free-standing gel.

9. The electrochromic medium according to claim 1, wherein said electrochromic medium comprises a crosslinked polymer matrix.

10. 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; and

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

at least one solvent;

an anodic material;

a cathodic material, wherein both of the anodic and cathodic materials are electroactive and at least one of the anodic and cathodic materials is electrochromic; and

an ultraviolet stabilizing material, wherein the ultraviolet stabilizing material includes a solubilizing moiety which serves to increase solubility of the ultraviolet stabilizing material relative to the same without the solubilizing moiety.

11. The electrochromic device according to claim 10, wherein the ultraviolet stabilizing material is represented by the formula:

wherein R₁ is OH;

wherein R₂-R₉ are the same or different and comprise H, OH, a halide, or a straight or branched alkyl, aryl, alkaryl, arakyl, alkoxy, or carboxy group containing 1 to approximately 20 carbon atoms; and

wherein at least one of R₂-R₉ is associated with a solubilizing moiety.

12. The electrochromic device according to claim 10, wherein the solubilizing moiety is represented by at least one of the following formulae:

wherein R₁₀-R₂₆ are the same or different and comprise H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing 1 to approximately 10 carbon atoms;

wherein m is an integer ranging from 1 to approximately 10;

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

wherein X is associated with the ultraviolet stabilizing material 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, one or more of structures I-X, and mixtures thereof.

13. The electrochromic device according to claim 10, wherein the solubilizing moiety is represented by the following formula:

wherein R₂₄ comprises H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing 1 to approximately 10 carbon atoms;

wherein m is an integer ranging from 1 to approximately 10;

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

wherein X is associated with the ultraviolet stabilizing material 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.

14. The electrochromic device according to claim 10, wherein the ultraviolet stabilizing material is selected from at least one of the group consisting of TP1, TP2, TP3, TPEG, and mixtures thereof.

15. The electrochromic device according to claim 10, 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.

16. The electrochromic device according to claim 10, wherein said electrochromic medium comprises a viscosity modifier.

17. The electrochromic device according to claim 10, wherein said electrochromic medium comprises a free-standing gel.

18. The electrochromic device according to claim 10, wherein said electrochromic medium comprises a crosslinked polymer matrix.

19. The electrochromic device according to claim 10, wherein the device is an electrochromic window.

20. The electrochromic device according to claim 10, wherein the second substrate is plated with a reflective material.

21. The electrochromic device according to claim 20, wherein the reflective material is selected from the group comprising chromium, rhodium, ruthenium, silver, alloys of the same, and mixtures thereof.

22. The electrochromic device according to claim 21, wherein the device is an electrochromic mirror.

23. 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; and

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

at least one solvent;

an anodic material;

a cathodic material, wherein both of the anodic and cathodic materials are electroactive and at least one of the anodic and cathodic materials is electrochromic; and

an ultraviolet stabilizing material, wherein the ultraviolet stabilizing material includes a solubilizing moiety which serves to increase solubility of the ultraviolet stabilizing material relative to the same without the solubilizing moiety, wherein the ultraviolet stabilizing material is represented by the formula;

wherein R₁ is OH;

wherein R₂-R₉ are the same or different and comprise H, OH, a halide, or a straight or branched alkyl, aryl, alkaryl, arakyl, alkoxy, or carboxy group containing 1 to approximately 20 carbon atoms; and

wherein at least one of R₂-R₉ is associated with a solubilizing moiety; and

wherein the solubilizing moiety is represented by at least one of the following formulae;

wherein R₁₀-R₂₆ are the same or different and comprise H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing 1 to approximately 10 carbon atoms;

wherein m is an integer ranging from 1 to approximately 10;

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

wherein X is associated with the ultraviolet stabilizing material 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, one or more of structures I-X, and mixtures thereof.

24. The electrochromic medium according to claim 23, wherein the solubilizing moiety is represented by the following formula:

wherein R₂₄ comprises H or a straight or branched alkyl, aryl, alkaryl, or aralkyl group containing 1 to approximately 10 carbon atoms;

wherein m is an integer ranging from 1 to approximately 10;

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

wherein X is associated with the ultraviolet stabilizing material 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.

25. The electrochromic device according to claim 24, 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.