# US 10,372,005 B2 · Organic electrochromic device, optical filter, lens unit, and imaging apparatus > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,372,005 B2 - Document ID: US10372005B2 - Status: Granted - Kind: B2 - Application number: 15/519,636 - Filed: 2015-11-04 - Published: 2017-08-24 - Granted: 2019-08-06 - Earliest claimed: 2014-11-06 - Assignees: Canon Kabushiki Kaisha - Applicants: Canon Kabushiki Kaisha - Inventors: Wataru Kubo; Shinjiro Okada; Kenji Yamada - Web page: https://patentgrep.com/patent/US10372005B2 ## CPC - G02F 1/1503: caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions - E06B 3/6722: {with adjustable passage of light} - G02F 1/163: Operation of electrochromic cells, e.g. electrodeposition cells; Circuit arrangements therefor - G09G 3/34: by control of light from an independent source - G09G 3/38: using electrochromic devices - C09K 9/02: Organic tenebrescent materials - E06B 2009/2464: {featuring transparency control by applying voltage, e.g. LCD, electrochromic panels} - G02F 1/15: based on an electrochromic effect - G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS - E06B: FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES (shades or blinds for greenhouses A01G9/22; curtains A47H; lids for car boots or bonnets B62D25/10; skylights E04B7/18; sunshades, awnings E04F10/00) - G09G: ARRANGEMENTS OR CIRCUITS FOR CONTROL OF INDICATING DEVICES USING STATIC MEANS TO PRESENT VARIABLE INFORMATION (arrangements for transferring data between digital computers and displays G06F3/14; static indicating arrangements comprising an association of a number of separate sources or light control cells G09F9/00; static indicating arrangements comprising integral associations of a number of light sources H01J, H01K, H10H, H05B33/12; scanning, transmission or reproduction of documents or the like, e.g. facsimile transmission, details thereof H04N1/00) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## 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 ### Claim 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. ### Claim 2 (depends on 1) 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. ### Claim 3 (depends on 1) 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. ### Claim 4 (depends on 1) 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. ### Claim 5 (depends on 1) 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. ### Claim 6 (depends on 1) 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. ### Claim 7 (depends on 1) 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. ### Claim 8 (depends on 1) 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. ### Claim 9 (depends on 1) 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. ### Claim 10 (depends on 1) The organic electrochromic device according to claim 1, wherein the redox substance is dissolved in the solvent. ### Claim 11 (depends on 1) 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. ### Claim 12 (depends on 1) 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. ### Claim 13 (depends on 1) 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. ### Claim 14 (depends on 1) The organic electrochromic device according to claim 1, wherein the redox substance is not an electrochromic material. ### Claim 15 (depends on 1) The organic electrochromic device according to claim 1, wherein an interelectrode distance of the pair of electrodes is 0.6 μm to 300 μm. ### Claim 16 (depends on 1) The organic electrochromic device according to claim 1, wherein an interelectrode distance of the pair of electrodes is 4 μm to 130 μm. ### Claim 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. ### Claim 18 (depends on 17) The organic electrochromic device according to claim 17, wherein the redox substance is not an electrochromic material. ### Claim 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. ### Claim 20 (depends on 19) The electrochromic device according to claim 19, wherein the redox substance is not an electrochromic material. ### Claim 21 (depends on 19) 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. ### Claim 22 (depends on 19) 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.