Near-IR absorptive compounds and devices incorporating the same

• US 10,745,613 B2
• Filed: 10/17/2017
• Issued: 08/18/2020
• Est. Priority Date: 10/17/2016
• Status: Active Grant

• Current Assignee: Gentex Corporation
• Original Assignee: Gentex Corporation
• Inventors: Giri, Punam
• Primary Examiner(s): Ahvazi, Brian
• Application Number:
  US15/786,167
• Publication Number:
  US 20180105738A1
• Time in Patent Office: 1,036 Days
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G02F 1/15 based on an electrochromic effect
• CPC Class Codes: G02F 1/1503 caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
• CPC Class Codes: G02F 2203/11 involving infrared radiation

Abstract

An electrochromic device includes a compound of Formula (I):

wherein: R¹ and R² are individually alkyl, alkoxy, or aryloxy; R³, R⁴, R⁵, R⁶, R⁷, R⁸ are individually H, alkoxy, or aryloxy; R⁹ and R¹⁰ are individually alkoxy, or aryloxy, or where R¹ and R² are alkyl, R⁹ and R¹⁰ are individually H, alkoxy, or aryloxy; and R¹¹ and R¹² are individually alkyl or —(CH₂)_nN⁺(R²⁰)³ [X], wherein n is from 1 to 20; each R²⁰ is individually alkyl; and X is an anion.

Claims

1. An electrochromic device comprising a compound of Formula (I):

2. The electrochromic device of claim 1, wherein R¹ and R² are individually C₁-C₁₂-alkoxy, a group of formula R²¹[O(CH₂)_x]_qO—

, or C₆-C₂₀-aryloxy, wherein R²¹ is alkyl, x is 1, 2, 3, or 4, and q is an integer from 1 to 20.

3. The electrochromic device of claim 1, wherein:

R¹ and R² are individually C₁-C₁₂-alkoxy;

R³, R⁴, R⁷, R⁸ are individually C₁-C₁₂-alkoxy;

R⁵ and R⁶ are H;

R⁹ and R¹⁰ are individually C₁-C₁₂-alkoxy;

R¹¹ and R¹² are individually C₁-C₁₂-alkyl; and

X is an anion.

4. The electrochromic device of claim 1, wherein:

R¹ and R² are individually methoxy, ethoxyl, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy, or t-butoxy;

R³, R⁴, R⁷, R⁸ are individually methoxy, ethoxyl, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy, or t-butoxy;

R⁵ and R⁶ are H;

R⁹ and R¹⁰ are individually methoxy, ethoxyl, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy, or t-butoxy;

R¹¹ and R¹² are individually methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, or t-butyl; and

X is an anion.

5. The electrochromic device of claim 1 further comprising an electrochromic medium comprising an anodic material comprising the compound of Formula (I).

6. The electrochromic device of claim 1, wherein the compound of Formula (I) is 2,3,4,6,9,10,11,13-octamethoxy-7-14-dimethyl triphenodithiazine;

3,6,10,13-tetramethoxy-7-14-dimethyl triphenodithiazine, or a mixture of any two or more thereof.

7. The electrochromic device of claim 1 which is a mirror, an architectural window, an aircraft window, a filter, or a battery.