Electrochromic element, optical filter, lens unit, image pickup apparatus, and window member

Patent metadata

Field	Value
Publication number	US-12078905-B2
Application number	US-202016841446-A
Country	US
Kind code	B2
Filing date	Apr 6, 2020
Priority date	Oct 10, 2017
Publication date	Sep 3, 2024
Grant date	Sep 3, 2024

Abstract

As an example of an EC element in which vertical color separation is suppressed, the present disclosure provides an EC element including a pair of electrodes, a solvent, an anodic EC compound, and a cathodic EC compound. In the EC element, the difference between a solvation free energy of an oxidized form of the anodic EC compound in water and a solvation free energy of the oxidized form in octanol is 35 kcal/mol or more, and the cathodic EC compound has a substituent containing any one element selected from halogens, sulfur, boron, phosphorus, and silicon.

First claim

The invention claimed is:

1. An electrochromic element comprising: a first electrode; a second electrode; and an electrochromic layer disposed between the first electrode and the second electrode, the electrochromic layer containing a solvent, an anodic electrochromic compound, and a cathodic electrochromic compound,
wherein the cathodic electrochromic compound has a substituent containing any one element selected from halogens, sulfur, boron, phosphorus, and silicon, and
the electrochromic element satisfies inequality (1):
G A+ H2O −G A+ OcOH ≥35  inequality (1)

where, in inequality (1), G A+ H2O represents a solvation free energy (kcal/mol) of an oxidized form of the anodic electrochromic compound in water, and G A+ OcOH represents a solvation free energy (kcal/mol) of the oxidized form of the anodic electrochromic compound in octanol.

2. The electrochromic element according to claim 1 , wherein the electrochromic element further satisfies inequality (2):
G A+ H2O −G A+ OcOH ≥44  inequality (2).

3. The electrochromic element according to claim 1 , wherein the cathodic electrochromic compound has a substituent containing a halogen.

4. The electrochromic element according to claim 1 , wherein the cathodic electrochromic compound has a substituent containing fluorine.

5. The electrochromic element according to claim 1 , wherein in the electrochromic layer, at least one of a concentration of the anodic electrochromic compound and a concentration of the cathodic electrochromic compound is 0.05 mol/L or more.

6. The electrochromic element according to claim 1 , wherein the anodic electrochromic compound is a dihydrophenazine derivative.

7. The electrochromic element according to claim 1 , wherein the cathodic electrochromic compound is a pyridine derivative.

8. The electrochromic element according to claim 7 , wherein the cathodic electrochromic compound has a viologen skeleton.

9. The electrochromic element according to claim 8 , wherein the cathodic electrochromic compound is a compound represented by general formula (11):

in general formula (11), X 1 and X 2 are each independently selected from an alkyl group, an aralkyl group, and an aryl group, the alkyl group, the aralkyl group, and the aryl group optionally having a substituent, R 11 to R 18 are each independently any one of a hydrogen atom, an alkyl group, an aralkyl group, an alkoxy group, an aryl group, a heterocyclic group, a substituted amino group, a halogen atom, and an acyl group, the alkyl group, the alkoxy group, the aralkyl group, the aryl group, and the heterocyclic group optionally having a substituent, A 1′ and A 2′ each independently represent a monovalent anion, and
at least one of X 1 , X 2 , and R 11 to R 18 is a substituent containing any one element selected from halogens, sulfur, boron, phosphorus, and silicon.

10. The electrochromic element according to claim 1 , wherein the solvent is a cyclic ether.

11. A lens unit comprising:
an optical filter including the electrochromic element according to claim 1 ; and
an image pickup optical system including a plurality of lenses.

12. An image pickup apparatus comprising:
an image pickup optical system including a plurality of lenses;
an optical filter including the electrochromic element according to claim 1 ; and
an image pickup element that receives light transmitted through the optical filter.

13. An image pickup apparatus to which an image pickup optical system including a plurality of lenses is attachable, the image pickup apparatus comprising:
an optical filter including the electrochromic element according to claim 1 ; and
an image pickup element that receives light transmitted through the optical filter.

14. A window member comprising:
a pair of substrates; and
the electrochromic element according to claim 1 ,
wherein the electrochromic element is disposed between the pair of substrates, and
the electrochromic element adjusts the amount of light transmitted through the pair of substrates.

15. An electrochromic element comprising: a first electrode; a second electrode; and an electrochromic layer disposed between the first electrode and the second electrode, the electrochromic layer containing a solvent, an anodic electrochromic compound, and a cathodic electrochromic compound,
wherein a difference between a solvation free energy of a colored form of the anodic electrochromic compound in water and a solvation free energy of the colored form of the anodic electrochromic compound in octanol is 35 kcal/mol or more, and
the cathodic electrochromic compound has a substituent containing any one element selected from halogens, sulfur, boron, phosphorus, and silicon.

Assignees

• Canon Kk

Inventors

• Kubo Wataru
• Yamada Kenji
• Igawa Satoshi
• Ito Yuto
• Kawata Isao

Classifications

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D241/46

  Phenazines · CPC title

• B32B17/10513 Primary

  Electrochromic layer · CPC title

• G02F2001/15145

  the electrochromic layer comprises a mixture of anodic and cathodic compounds · CPC title

• E06B3/6722

  with adjustable passage of light · CPC title