Organic electrochromic device, optical filter, lens unit, and imaging apparatus

• US 10,372,005 B2
• Filed: 11/04/2015
• Issued: 08/06/2019
• Est. Priority Date: 11/06/2014
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Kubo, Wataru, Okada, Shinjiro, Yamada, Kenji
• Primary Examiner(s): Ben, Loha
• Application Number:
  US15/519,636
• Publication Number:
  US 20170242314A1
• Time in Patent Office: 1,371 Days
• Field of Search: 359265-275, 345 49, 345105, 438238
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: E06B 2009/2464 featuring transparency control by applying voltage, e.g. LCD, electrochromic panels
• CPC Class Codes: E06B 3/6722 with adjustable passage of light
• 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 1/163 Operation of electrochromic cells, e.g. electrodeposition cells; Circuit arrangements therefor
• CPC Class Codes: G09G 3/34 by control of light from an independent source
• CPC Class Codes: G09G 3/38 using electrochromic devices

Abstract

Provided is an organic electrochromic device which has a high response speed and is excellent in durability even when a large current is flowed transiently, in which: an electrochromic layer arranged between a pair of electrodes contains an organic electrochromic material, a redox substance, and a solvent; the organic electrochromic material and the redox substance are each a material to be reversibly subjected to a redox reaction; and a potential at which the redox substance is oxidized (or reduced) is present between a potential at which the organic electrochromic material is reversibly oxidized (or reduced) and a potential at which the organic electrochromic material is irreversibly oxidized (or reduced).

Claims

1. An organic electrochromic device, comprising:

a pair of electrodes; and

an electrochromic layer arranged between the pair of electrodes,

wherein;

the electrochromic layer contains an organic electrochromic material, a redox substance, and a solvent;

the organic electrochromic material and the redox substance each comprise a material to be reversibly subjected to a redox reaction;

a peak change amount of a molar absorption coefficient caused by the redox reaction of the redox substance is ¼

or less than that of the organic electrochromic material; and

a potential at which the redox substance is oxidized is present between a potential at which the organic electrochromic material is reversibly oxidized and a potential at which the organic electrochromic material is irreversibly oxidized, or a potential at which the redox substance is reduced is present between a potential at which the organic electrochromic material is reversibly reduced and a potential at which the organic electrochromic material is irreversibly reduced.

2. The organic electrochromic device according to claim 1, wherein a voltage at which the organic electrochromic device is driven is applied within a range between the potential at which the redox substance is oxidized and the potential at which the redox substance is reduced.

3. The organic electrochromic device according to claim 1, wherein a half-wave potential of an oxidation reaction of the redox substance is present between a half-wave potential in a reversible oxidation reaction of the organic electrochromic material and a half-wave potential in an irreversible oxidation reaction of the organic electrochromic device in a cyclic voltammogram of the organic electrochromic material.

4. The organic electrochromic device according to claim 1, wherein a half-wave potential of a reduction reaction of the redox substance is present between a half-wave potential in a reversible reduction reaction of the organic electrochromic material and a half-wave potential in an irreversible reduction reaction of the organic electrochromic device in a cyclic voltammogram of the organic electrochromic material.

5. The organic electrochromic device according to claim 1, wherein the redox substance is free of electrochemical oxidization at a potential at which the organic electrochromic material starts to be reversibly oxidized.

6. The organic electrochromic device according to claim 1, wherein the redox substance is free of electrochemical reduction at a potential at which the organic electrochromic material starts to be reversibly reduced.

7. The organic electrochromic device according to claim 1, wherein a value of current resulting from a reaction of the redox substance at a half-wave potential of a reversible oxidation reaction of the organic electrochromic material is ⅕

or less of a value of current resulting from the reversible oxidation reaction of the organic electrochromic material.

8. The organic electrochromic device according to claim 1, wherein a value of current resulting from a reaction of the redox substance at a half-wave potential of a reversible reduction reaction of the organic electrochromic material is ⅕

or less of a value of current resulting from the reversible reduction reaction of the organic electrochromic material.

9. The organic electrochromic device according to claim 1, wherein the electrochromic material and the redox substance satisfy formula (A):

R/S≥

0.2 

 

(A)

wherein, in the formula (A), R represents a molar amount per number of electrons of a reaction of the redox substance contained in the electrochromic layer, and S represents a molar amount per number of electrons of a reaction of the organic electrochromic material with reference to the redox substance.

10. The organic electrochromic device according to claim 1, wherein the redox substance is dissolved in the solvent.

11. A lens unit, comprising:

the electrochromic device of claim 1;

an active device connected to the electrochromic device; and

an optical system including a plurality of lenses.

12. An imaging apparatus, comprising:

the organic electrochromic device of claim 1;

an active device connected to the organic electrochromic device; and

an imaging device configured to receive light which has passed through the organic electrochromic device.

13. A window member, comprising:

a pair of transparent substrates;

the organic electrochromic device of claim 1 disposed between the pair of transparent substrates; and

an active device connected to the organic electrochromic device.

14. The organic electrochromic device according to claim 1, wherein the redox substance is not an electrochromic material.

15. The organic electrochromic device according to claim 1, wherein an interelectrode distance of the pair of electrodes is 0.6 μ

m to 300 μ

m.

16. The organic electrochromic device according to claim 1, wherein an interelectrode distance of the pair of electrodes is 4 μ

m to 130 μ

m.

17. An organic electrochromic device, comprising:

a pair of electrodes; and

an electrochromic layer arranged between the pair of electrodes,

wherein;

the electrochromic layer contains an organic electrochromic material, a redox substance, and a solvent;

the organic electrochromic material and the redox substance each comprise a material to be reversibly subjected to a redox reaction;

a peak change amount of a molar absorption coefficient caused by the redox reaction of the redox substance is ¼

or less than that of the organic electrochromic material; and

the organic electrochromic material has a first oxidation potential and a second oxidation potential, and an oxidation potential of the redox substance is present between the first oxidation potential and the second oxidation potential, or

the organic electrochromic material has a first reduction potential and a second reduction potential, and a reduction potential of the redox substance is present between the first reduction potential and the second reduction potential.

18. The organic electrochromic device according to claim 17, wherein the redox substance is not an electrochromic material.

19. An organic electrochromic device, comprising:

a pair of electrodes; and

an electrochromic layer arranged between the pair of electrodes,

wherein;

the electrochromic layer contains an organic electrochromic material, a redox substance, and a solvent;

the organic electrochromic material and the redox substance each comprise a material to be reversibly subjected to a redox reaction; and

the organic electrochromic material has a first oxidation potential and a second oxidation potential, and an oxidation potential of the redox substance is present between the first oxidation potential and the second oxidation potential, wherein a value of current resulting from a reaction of the redox substance at a half-wave potential of a first oxidation reaction of the organic electrochromic material is ⅕

or less of a value of current resulting from the first oxidation reaction of the organic electrochromic material;

or

the organic electrochromic material has a first reduction potential and a second reduction potential, and a reduction potential of the redox substance is present between the first reduction potential and the second reduction potential, wherein a value of current resulting from a reaction of the redox substance at a half-wave potential of a first reduction reaction of the organic electrochromic material is ⅕

or less of a value of current resulting from the first reduction reaction of the organic electrochromic material.

20. The electrochromic device according to claim 19, wherein the redox substance is not an electrochromic material.

21. An imaging apparatus, comprising:

the organic electrochromic device of claim 19;

an active device connected to the organic electrochromic device; and

an imaging device configured to receive light which has passed through the organic electrochromic device.

22. A window member, comprising:

a pair of transparent substrates;

the organic electrochromic device of claim 19 disposed between the pair of transparent substrates; and

an active device connected to the organic electrochromic device.