Electrochromic compounds and associated media and devices

• US 7,428,091 B2
• Filed: 11/10/2005
• Issued: 09/23/2008
• Est. Priority Date: 11/15/2004
• Status: Active Grant

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Guarr, Thomas F., Franz, Sue F., Giri, Punam, Baumann, Kelvin L., Muyskens, Mark D.
• Primary Examiner(s): Mack; Ricky
• Assistant Examiner(s): Tra; Tuyen Q
• Application Number:
  US11/272,552
• Publication Number:
  US 20060103911A1
• Time in Patent Office: 1,048 Days
• Field of Search: 359265-275, 359/296, 544/347, 345/49, 345/105, 345/107, 348/817
• US Class Current: 359/265
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• 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 comprising: a material represented by the following formula:

wherein X comprises N—R₁₀, O, or S; wherein R₁-R₁₀ are defined herein with the proviso that at least one of R₅ and R₁₀ comprises an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkenyl, and/or alkynyl group containing 4 to approximately 50 carbon atoms, wherein at least one of the carbon atoms 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, and wherein at least one of R₅ and R₁₀ is void of any β hydrogen atoms.

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 anodic electroactive material is represented by the following formula;

wherein X comprises N—

R₁₀, O, or S;

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) and/or a silyl or siloxyl group containing approximately 1 to approximately 50 silicon atom(s), wherein the carbon and/or silicon atom(s) can 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 at least one of R₅ and R₁₀ comprises an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkenyl, and/or alkynyl group containing 4 to approximately 50 carbon atoms, wherein at least one of the carbon atoms can 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, and wherein at least one of R₅ and R₁₀ is void of any β

hydrogen atoms.

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 anodic electroactive material is represented by the following formula;

wherein X comprises N—

R₁₀, O, or S;

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) and/or a silyl or siloxyl group containing approximately 1 to approximately 50 silicon atom(s), wherein the carbon and/or silicon atom(s) can 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 at least one of R₅ and R₁₀ comprises an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkenyl, and/or alkynyl group containing 4 to approximately 50 carbon atoms, wherein at least one of the carbon atoms can 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, and wherein at least one of R₅ and R₁₀ is void of any β

hydrogen atoms.

3. The electrochromic medium according to claim 2, wherein X comprises N—

R₁₀;

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) and/or a silyl or siloxyl group containing approximately 1 to approximately 50 silicon atom(s), wherein the carbon and/or silicon atom(s) can 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 both R₅ and R₁₀ comprise an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkenyl, and/or alkynyl group containing 4 to approximately 50 carbon atoms, wherein at least one of the carbon atoms can 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, and wherein both of R₅ and R₁₀ are void of any β

hydrogen atoms.

4. The electrochromic medium according to claim 2, wherein at least one of R₅ and R₁₀ comprises an alkyl group containing approximately 5 to approximately 20 carbon atoms.

5. 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 4 contained within a chamber positioned between the first and second substrates.

6. The electrochromic medium according to claim 2, wherein R₅ and R₁₀ comprise alkyl groups containing approximately 5 to approximately 20 carbon atoms.

7. The electrochromic medium according to claim 2, wherein at least one of R₅ and R₁₀ comprises a neopentyl group.

8. 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 7 contained within a chamber positioned between the first and second substrates.

9. The electrochromic medium according to claim 2, wherein R₅ and R₁₀ comprise neopentyl groups.

10. The electrochromic medium according to claim 2, wherein R₅ and R₁₀ consist of neopentyl groups.

11. An electrochromic device, comprising:

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

the electrochromic medium according to claim 10.

12. 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 10 contained within a chamber positioned between the first and second substrates.

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

14. The electrochromic medium according to claim 2, wherein R₅ and R₁₀ are void of a benzyl group.

15. 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.

16. An electrochromic device, comprising:

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

the electrochromic medium according to claim 2.

17. The electrochromic device according to claim 16, wherein the device comprises an electrochromic window.

18. The electrochromic device according to claim 16, wherein a substrate is coated with a reflective material.

19. The electrochromic device according to claim 18, wherein the device comprises an electrochromic mirror.

20. The electrochromic device according to claim 19, wherein the device comprises a metallic ring around a perimeter.

21. The electrochromic device according to claim 16, wherein a substrate is less than approximately 1.0 mm thick.

22. The electrochromic device according to claim 17, where the device is an aircraft transparency.

23. The electrochromic device according to claim 16, wherein a substrate comprises a hydrophilic coating.

24. The electrochromic device according to claim 16, wherein the device exhibits a reduced charge transfer band in a solution with a viologen compared to 5,10-dimethyl-5,10-dihydrophenazine.

25. 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 the at least one anodic electroactive material comprises a 5,10-dialkyl-5,10-dihydrophenazine compound, wherein at least one alkyl group attached to the phenazine compound comprises at least 4 carbon atoms and is void of any β

hydrogen atoms.