Protic-soluble organic electrochromic compounds

• US 9,939,701 B2
• Filed: 03/09/2016
• Issued: 04/10/2018
• Est. Priority Date: 11/20/2015
• Status: Active Grant

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Baumann, Kelvin L., Lin, Rongguang, Giri, Punam, Franz, Sue
• Primary Examiner(s): NORTHINGTON DAVI, ZINNA
• Application Number:
  US15/065,808
• Publication Number:
  US 20170146880A1
• Time in Patent Office: 762 Days
• Field of Search: None
• 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: C07D 241/46 Phenazines
• 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: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G02F 1/1516 comprising organic material
• 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

Protic-soluble electrochromic materials, ion-paired electrochromic materials including protic-soluble electrochromic materials, as well as electrochromic media and electrochromic devices incorporating such materials, are provided. The use of protic solvent mixtures, especially mixtures incorporating water, allows for the use of a wider variety of substrate materials. For example, plastics that may be soluble in organic aprotic solvent systems may be used in water-based devices.

Claims

1. An electrochromic medium comprising a cathodic material, an anodic material, and a liquid or gel that comprises a protic solvent;

wherein the electrochromic medium comprises at least one of

a cathodic protic-soluble electrochromic material represented by Formula (I);

2. The electrochromic medium of claim 1, wherein in Formula (II)

R¹² and R²¹ are each independently —

(CH₂)_s—

CO₂⁻

, —

(CH₂)_t—

P(O)(OH)(O⁻

), —

(CH₂)_u—

OP(O)(OH)(O⁻

), or —

(CH₂)_w—

S(O)₂O⁻

; and

s, t, u, and w are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

3. The electrochromic medium of claim 1, wherein in Formula (III)

R²³ and R²⁸ are each independently alkyl, —

(CH₂)_m′

—

CO₂⁻

, —

(CH₂)_n′

—

P(O)(OH)(O⁻

), —

(CH₂)_p′

—

OP(O)(OH)(O⁻

), or —

(CH₂)_q′

—

S(O)₂O⁻

; and

m′

, n′

, p′

, and q′

are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

4. The electrochromic medium of claim 1, wherein the cathodic protic-soluble electrochromic material of Formula (I) is

5. The electrochromic medium of claim 1, wherein the anodic protic-soluble electrochromic material of Formula (III) is

6. The electrochromic medium of claim 1, wherein the anodic protic-soluble electrochromic material of Formula (V) is

7. The electrochromic medium of claim 1, wherein the protic solvent comprises an alcohol, a carboxylic acid, a primary amino compound, a secondary amino compound, water, or a mixture of any two or more thereof.

8. The electrochromic medium of claim 1, wherein the protic solvent comprises methanol, ethanol, isopropanol, trifluoroethanol, butanol, ethylene glycol, propylene glycol, water, or a mixture of any two or more thereof.

9. The electrochromic medium of claim 1, wherein the protic solvent comprises a diol.

10. The electrochromic medium of claim 1, wherein the amount of protic solvent in the liquid or gel is from about 40 wt % to about 100 wt %.