Electrochromic compounds with improved color stability in their radical states

• US 10,040,763 B2
• Filed: 02/10/2016
• Issued: 08/07/2018
• Est. Priority Date: 02/11/2015
• Status: Active Grant

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Lin, Rongguang, Baumann, Kelvin L., Giri, Punam, Nemes, Joel C., Kloeppner, Leroy J., Theiste, David A.
• Primary Examiner(s): Carcanague, Daniel R
• Application Number:
  US15/040,946
• Publication Number:
  US 20160229803A1
• Time in Patent Office: 909 Days
• Field of Search: 546255
• CPC Class Codes: C07D 213/04 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 213/22 containing two or more pyridine rings directly linked together, e.g. bipyridyl
• CPC Class Codes: C07F 17/02 of metals of Groups 8, 9 or 10 of the Periodic System
• CPC Class Codes: C07F 9/58 Pyridine rings
• CPC Class Codes: C08G 18/246 containing also tin-carbon bonds
• CPC Class Codes: C08G 18/3293 containing heterocyclic groups
• CPC Class Codes: C08G 18/6229 Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: G02F 1/1516 comprising organic material
• CPC Class Codes: G02F 1/15165 Polymers

Abstract

The invention relates to an electrochromic device and uses thereof, wherein the electrochromic device includes an electrochromic compound with reduced intermolecular interactions resulting in uncontrolled color changes represented by Formula (I):

Claims

1. An electrochromic device comprising:

a non-dimerizing electrochromic compound represented by Formula (I);

2. The electrochromic device of claim 1, wherein R¹¹, R¹², R¹³, and R¹⁴ are individually H or alkyl.

3. The electrochromic device of claim 1, wherein R¹¹, R¹², R¹³, and R¹⁴ are H, and R¹⁵ is methoxy, ethoxy, propoxy, ethyl, propyl, iso-propyl, butyl, sec-butyl, or tert-butyl.

4. The electrochromic device of claim 1, wherein R¹⁷ is alkyl or siloxy alkyl.

5. The electrochromic device of claim 1, wherein R¹ and R² are individually aralkyl, C₁-C₁₂ alkyl or C₁-C₁₂ hydroxyalkyl.

8. The electrochromic device of claim 1, wherein R⁴, R⁶, R⁸, and R¹⁰ are individually H, OH, or alkyl.

9. The electrochromic device of claim 1, wherein X⁻

is F⁻

, Cl⁻

, Br⁻

, I⁻

, BF₄⁻

, PF₆⁻

, SbF₆⁻

, AsF₆⁻

, ClO₄⁻

, SO₃CF₃⁻

, N(CN)₂⁻

, N(CF₃SO₂)₂⁻

, C(CF₃SO₂)₃⁻

, N(SO₂C₂F₅)₂⁻

, ⁻

Al(OC(CF₃)₃)₄ or ⁻

BAr₄, wherein Ar is a aryl or fluorinated aryl group.

10. The electrochromic device of claim 1 further comprising:

an electrochromic medium comprising the non-dimerizing electrochromic compound; and

a chamber defined by a first conductive surface of first substrate, a second conductive surface of a second substrate, and a sealing member joining the first substrate to the second substrate,

wherein the electrochromic medium is disposed within the chamber.

11. The electrochromic device of claim 10 further comprising an anodic component and a solvent.

12. The electrochromic device of claim 1, wherein R³ and R⁵ are each a group of Formula (II) and R¹⁵ is —

OC(O)NR¹⁶R¹⁷.

13. The electrochromic device of claim 1, wherein R¹⁵ is OC(O)NH(CH₂)—

Si(OEt)₃.

14. The electrochromic device of claim 1, wherein R³ and R⁵ are each a group of Formula (II) and R¹⁵ is OC(O)NH(CH₂)_nSi(OEt)₃.

6. An electrochromic device comprising:

a non-dimerizing electrochromic compound represented by Formula (III);

7. The electrochromic device of claim 6, wherein R¹⁹ is (CH₂)_3-8 or 1,4-phenylene.