Electrochromic compounds and associated media and devices

• US 7,855,821 B2
• Filed: 08/25/2008
• Issued: 12/21/2010
• Est. Priority Date: 11/15/2004
• Status: Active Grant

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Guarr, Thomas F., Theiste, David A., Baumann, Kelvin L.
• Primary Examiner(s): Ben; Loha
• Application Number:
  US12/229,606
• Publication Number:
  US 20080316574A1
• Time in Patent Office: 848 Days
• Field of Search: 359/265, 359273-275, 252/62.2, 252/500, 252/582, 252/583, 252/586
• US Class Current: 359/273
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• 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

An electrochromic device having an electrochromic medium which includes a compound represented by the following formula:

wherein R₁-R₁₀ are the same or different and comprise H, an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkenyl, and/or alkynyl group containing approximately 1 to approximately 50 carbon atom(s), wherein the carbon atom(s) may be a linking group to, or part of, a halogen, a N, O, and/or S containing moiety, and/or one or more functional groups comprising alcohols, esters, ammonium salts, phosphonium salts, and combinations thereof; with the proviso that R₂ and R₇ each comprise at least two carbon atoms, at least one of R₂ and R₇ comprises less than 2 β hydrogen atoms and is void of a benzyl group.

Claims

1. 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 comprising;

at least one solvent;

at least one anodic electroactive material;

at least one cathodic electroactive material;

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

wherein at least one cathodic electroactive material is represented by the following formula;

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

at least one solvent;

at least one anodic electroactive material;

at least one cathodic electroactive material;

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

wherein at least one cathodic electroactive material is represented by the following formula;

3. The electrochromic medium according to claim 2, wherein at least one of R₂ and R₇ is void of any β

hydrogen atoms.

4. The electrochromic medium according to claim 2, wherein R₂ and R₇ are void of any β

hydrogen atoms.

5. The electrochromic medium according to claim 2, wherein at least one of R₂ and R₇ comprises an alkyl group containing approximately 5 to approximately 20 carbon atoms.

6. The electrochromic medium according to claim 2, wherein R₂ and R₇ comprise alkyl groups containing approximately 5 to approximately 20 carbon atoms.

7. The electrochromic medium according to claim 2, wherein at least one of R₂ and R₇ consists of an alkyl group containing approximately 5 to approximately 20 carbon atoms.

8. The electrochromic medium according to claim 2, wherein R₂ and R₇ consist of alkyl groups containing approximately 5 to approximately 20 carbon atoms.

9. The electrochromic medium according to claim 2, wherein at least one of R₂ and R₇ comprises an electron-donating group pending from a β

carbon atom.

10. The electrochromic medium according to claim 9, wherein the electron-donating group comprises a hydroxyl group, a straight or branched alkyl group containing 1 to approximately 50 carbon atom(s), alcohols, amines, phosphines, ethers, esters, amides, nitriles, olefins, and combinations thereof.

11. The electrochromic medium according to claim 2, wherein R₂ and R₇ comprise an electron-donating group pending from a β

carbon atom.

12. The electrochromic medium according to claim 11, wherein the electron-donating group comprises a hydroxyl group, a straight or branched alkyl group containing 1 to approximately 50 carbon atom(s), alcohols, amines, phosphines, ethers, esters, amides, nitriles, olefins, and combinations thereof.

13. The electrochromic medium according to claim 2, wherein at least one of R₂ and R₇ comprises a 2-ethylhexyl group.

14. The electrochromic medium according to claim 2, wherein R₂ and R₇ comprise 2-ethylhexyl groups.

15. The electrochromic medium according to claim 2, wherein at least one of R₂ and R₇ comprises a neopentyl group.

16. The electrochromic medium according to claim 2, wherein R₂ and R₇ comprise neopentyl groups.

17. The electrochromic medium according to claim 2, wherein R₂ and R₇ consist of 2-ethylhexyl groups.

18. The electrochromic medium according to claim 2, wherein R₂ and R₇ consist of neopentyl groups.

19. The electrochromic medium according to claim 2, wherein R₁-R₁₀ are void of a benzyl group.

20. The electrochromic medium according to claim 2, wherein R₂ and R₇ are void of a benzyl group.

21. 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 according to claim 20 contained within a chamber positioned between the first and second substrates.

22. The electrochromic medium according to claim 2, wherein the electrochromic medium further comprises at least one of a cross-linked polymer matrix, a free-standing gel, and a substantially non-weeping gel.

23. An electrochromic device, comprising:

at least one substrate having an electrically conductive material associated therewith; and

the electrochromic medium according to claim 2.

24. The electrochromic device according to claim 23, wherein the device comprises an electrochromic window.

25. The electrochromic device according to claim 23, wherein a substrate is coated with a reflective material.

26. The electrochromic device according to claim 24, wherein the device comprises an electrochromic mirror.

27. The electrochromic device according to claim 26, wherein the device comprises a metallic ring around a perimeter thereof.

28. The electrochromic device according to claim 23, wherein a substrate is less than approximately 1.0 mm thick.

29. The electrochromic device according to claim 28, where the device is an aircraft transparency.

30. The electrochromic device according to claim 23, wherein a substrate comprises a hydrophilic coating.