Electrochromic composition and electrochromic element

Patent metadata

Field	Value
Publication number	US-9969931-B2
Application number	US-201515317372-A
Country	US
Kind code	B2
Filing date	Jun 30, 2015
Priority date	Jul 11, 2014
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

An electrochromic composition has an anodic electrochromic compound and a cathodic electrochromic compound, in which the anodic electrochromic compound is represented by General Formula [1]

and the cathodic electrochromic compound is represented by General Formula [2]

In General Formula 1, A 1 to A 4 represent substituents, R 1 and R 2 , and R 20 and R 21 represent a hydrogen atom or a substituent. n is an integer of 1 to 5. X represents a thiophene derivative and Y- represents an anion.

First claim

The invention claimed is:

1. An electrochromic composition comprising:
an anodic electrochromic compound; and
a cathodic electrochromic compound,
wherein the anodic electrochromic compound is represented by General Formula [1] and the cathodic electrochromic compound is represented by General Formula [2],

wherein, in General Formula [1], A 1 to A 4 each independently represent a substituent selected from alkyl groups in which the number of carbon atoms is 1 or more and 20 or less, alkoxy groups in which the number of carbon atoms is 1 or more and 20 or less, and aryl groups which optionally have a substituent,

wherein, when the aryl group has a substituent, the substituent is at least any one of alkyl groups in which the number of carbon atoms is 1 or more and 8 or less or alkoxy groups in which the number of carbon atoms is 1 or more and 8 or less,
wherein R 1 and R 2 each are independently selected from hydrogen atoms or substituents, the substituents represented by R 1 and R 2 above each are at least any one of halogen atoms, alkyl groups in which the number of carbon atoms is 1 or more and 20 or less, alkoxy groups in which the number of carbon atoms is 1 or more and 20 or less, alkyl ester groups in which the number of carbon atoms is 1 or more and 20 or less, aryl groups which optionally have a substituent, amino groups which optionally have a substituent, or cyano groups, and two or more R 1 s and R 2 s optionally being present,
wherein n is an integer of 1 to 5,
wherein, in General Formula [2], R 20 and R 21 each are independently selected from hydrogen atoms or substituents, the substituents represented by R 20 and R 21 each are at least any one selected from halogen atoms, alkyl groups in which the number of carbon atoms is 1 or more and 20 or less, alkoxy groups in which the number of carbon atoms is 1 or more and 20 or less, alkyl ester groups in which the number of carbon atoms is 1 or more and 20 or less, acyl groups in which the number of carbon atoms is 1 or more and 20 or less, aryl groups which optionally have a substituent, amino groups which optionally have a substituent, or cyano groups, two or more R 20 s and R 21 s optionally being present, and Y − represents an anion,
wherein X shown in Formula [1], is a structure of any one of General Formulae [3] to [5], in which when n is 2 or more, a plurality of Xs each are independently selected from the following general formulae [3] to [5],

wherein, in General Formula [3], R 3 represents an alkylene group in which the number of carbon atoms is 1 or more and 20 or less and which optionally be branched, and
wherein, in General Formula [4] and [5], R 4 to R 7 each represent a hydrogen atom or a substituent, and the substituents represented by R 4 to R 7 above each are at least any one of halogen atoms, alkyl groups in which the number of carbon atoms is 1 or more and 20 or less, alkoxy groups in which the number of carbon atoms is 1 or more and 20 or less, aryl groups which optionally have a substituent, alkyl ester groups in which the number of carbon atoms is 1 or more and 20 or less, amino groups which optionally have a substituent, or cyano groups.

2. The electrochromic composition according to claim 1 , wherein at least either one of A 1 or A 2 is an alkoxy group in which the number of carbon atoms is 1 or more and 20 or less.

3. The electrochromic composition according to claim 1 , wherein at least either one of A 3 or A 4 is an alkoxy group in which the number of carbon atoms is 1 or more and 20 or less.

4. The electrochromic composition according to claim 1 , wherein the alkoxy group represented by at least either one of A 1 or A 2 is a methoxy group or an isopropoxy group, and the alkoxy group represented by at least either one of A 3 or A 4 is a methoxy group or an isopropoxy group.

5. The electrochromic composition according to claim 1 , wherein R 20 and R 21 above are electron withdrawing substituents.

6. The electrochromic composition according to claim 5 , wherein R 20 and R 21 above each are any one of a tert-butyl group, a trifluoromethyl group, a methoxy group, a benzyloxy group, a methyl ester group, or a cyano group.

7. The electrochromic composition according to claim 1 , wherein a weight ratio of the electrochromic compound represented by General Formula [1] is 10% by mol or more and 90% by mol or less when a total of the electrochromic compound represented by General Formula [1] and the electrochromic compound represented by General Formula [2] is 100% by mol.

8. The electrochromic composition according to claim 1 comprising a third electrochromic compound which is different from the electrochromic compound represented by General Formula [1] and the electrochromic compound represented by General Formula [2].

9. The electrochromic composition according to claim 1 further comprising a solvent and an electrolyte.

10. The electrochromic composition according to claim 9 , wherein a concentration of the electrolyte is larger than 0 mol/l and 10 mol/l or less based on the solvent.

11. An electrochromic element comprising:
a pair of electrodes; and an electrochromic layer disposed between the pair of electrodes, wherein the electrochromic layer has the electrochromic composition according to claim 1 .

12. An optical filter comprising:
the electrochromic element according to claim 11 ; and
an active element connected to the electrochromic element.

13. A lens unit comprising:
the optical filter according to claim 12 ; and
an imaging optical system having a plurality of lenses.

14. An imaging device comprising:
the optical filter according to claim 12 ;
an imaging optical system; and
an image pickup device which performs imaging through the optical filter.

15. An imaging device, which is an imaging device to which an imaging optical system can be attached, the imaging device comprising:
the optical filter according to claim 12 ; and
an image pickup device which receives light passing through the optical filter.

16. A window material comprising:
a pair of transparent substrates; and
the electrochromic element according to claim 11 .

Assignees

• Canon Kk

Inventors

• Yamada Kenji
• Okada Shinjiro
• Yamamoto Jun

Classifications

• H04N23/54

  Mounting of pick-up tubes, electronic image sensors, deviation or focusing coils · CPC title

• G02F1/157

  Structural association of cells with optical devices, e.g. reflectors or illuminating devices · CPC title

• G02F1/155

  Electrodes · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title