Protic-soluble organic electrochromic compounds

• US 10,466,562 B2
• Filed: 04/03/2018
• Issued: 11/05/2019
• 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 F.
• Primary Examiner(s): Davis, Zinna Northington
• Application Number:
  US15/944,521
• Publication Number:
  US 20180224706A1
• Time in Patent Office: 581 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 ion-paired electrochromic material comprising a net positive cathodic electrochromic compound of Formula (VII), (VIII), or (IX) and a net negative anodic electrochromic compound of Formula (IVa), (Va), (VIa), or (Ma);

wherein the ion-paired electrochromic material has a net charge of zero and does not include a non-electrochromic ion;

wherein in Formula (VII), (VIII), and (IX)

2. An electrochromic medium comprising

an ion-paired electrochromic material of claim 1;

and

a liquid or gel that comprises a protic solvent.

3. An electrochromic device comprising:

the electrochromic medium of claim 2; 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.

4. An ion-paired electrochromic material comprising a net negative cathodic electrochromic compound of Formula (IIa) and a net positive anodic electrochromic compound of Formula (X), (XI), (XII), or (XIII), wherein the ion-paired electrochromic material has a net charge of zero and does not include a non-electrochromic ion;

wherein in Formula (IIa);

5. An electrochromic medium comprising

an ion-paired electrochromic material of claim 4;

and

a liquid or gel that comprises a protic solvent.

6. An electrochromic device comprising:

the electrochromic medium of claim 5; 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.

7. A compound of Formula: