Electrochromic compounds with improved color stability in their radical states

• US 10,464,900 B2
• Filed: 06/04/2018
• Issued: 11/05/2019
• 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:
  US15/997,358
• Publication Number:
  US 20180346421A1
• Time in Patent Office: 519 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

An electrochromic device includes an electrochromic compound with reduced intermolecular interactions resulting in uncontrolled color changes, the electrochromic 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 R³, R⁵, R⁷, and R⁹ are individually secondary alkyl, tertiary alkyl, or aryl.

3. The electrochromic device of claim 1, wherein R³ and R⁵ are individually aryl.

4. The electrochromic device of claim 3, wherein the aryl is a group of Formula (II):

5. The electrochromic device of claim 4, wherein R¹¹, R¹², R¹³, and R¹⁴ are individually H or alkyl.

6. The electrochromic device of claim 4, wherein R¹¹, R¹², R¹³, and R¹⁴ are H, and R¹⁵ is H, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, or tert-butyl.

7. The electrochromic device of claim 4, wherein R¹⁷ is H, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, or —

(CH₂)_nSi(OR¹⁸)₃, R¹⁸ is H or alkyl, and n is 1 to 10.

8. The electrochromic device of claim 1, wherein R³ and R⁵ are aryl and R⁷ and R⁹ are H.

9. The electrochromic device of claim 3, wherein the aryl is a group of Formula (II):

10. The electrochromic device of claim 9, wherein R¹¹, R¹², R¹³, and R¹⁴ are individually H or alkyl.

11. The electrochromic device of claim 9, wherein R¹¹, R¹², R¹³, and R¹⁴ are H, and R¹⁵ is methoxy, ethoxy, propoxy, ethyl, propyl, iso-propyl, butyl, sec-butyl, or tert-butyl.

12. The electrochromic device of claim 1, wherein R¹ and R² are individually,

13. The electrochromic device of claim 9, wherein R¹ and R² are individually —

(CH₂)_nSi(OH)₃, —

(CH₂)_nSi(OMe)₃, —

(CH₂)_nSi(OEt)₃,

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

15. 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.

16. The electrochromic device of claim 1 further comprising:

an electrochromic medium comprising the non-dimerizing electrochromic compound, an anodic component, and a solvent; 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.

17. A compound represented by Formula (I):