# US 10,310,350 B2 · Organic compound, electrochromic compound, and electrochromic element, optical filter, lens unit, imaging device, and window component having same

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- Number: US 10,310,350 B2
- Document ID: US10310350B2
- Status: Granted
- Kind: B2
- Application number: 15/591,832
- Filed: 2017-05-10
- Published: 2017-11-16
- Granted: 2019-06-04
- Earliest claimed: 2016-05-12
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Satoshi Igawa; Jun Yamamoto; Kenji Yamada; Tetsuya Tamura
- Web page: https://patentgrep.com/patent/US10310350B2

## CPC

- G02F 1/1516: comprising organic material
- C07C 311/48: having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07D 213/22: containing two or more pyridine rings directly linked together, e.g. bipyridyl
- C07D 213/65: attached in position 3 or 5
- C07F 9/65583: {each of the hetero rings containing nitrogen as ring hetero atom}
- C09K 9/02: Organic tenebrescent materials
- E06B 9/24: Screens or other constructions affording protection against light, especially against sunshine; Similar screens for privacy or appearance; {Slat blinds}(operating, guiding or securing devices or arrangements for roll-type closures E06B9/56; free-hanging flexible screens A47H23/00)
- G02C 7/10: Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
- G02F 1/1503: caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
- G02F 1/157: Structural association of cells with optical devices, e.g. reflectors or illuminating devices
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- E06B 2009/2464: {featuring transparency control by applying voltage, e.g. LCD, electrochromic panels}
- G02F 2001/1502: {complementary cell}
- G02F 2001/1518: {Ferrocene compounds}
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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)
- G02C: SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES (trial frames for testing the eyes A61B3/04; goggles or eyeshields not having the same features as spectacles A61F9/00)

## Abstract

An organic compound represented by General Formula (1), in which, in General Formula (1), R1 represents an alkyl group or an alkoxy group, X1 and X2 are each independently selected from an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, and A1− and A2− each independently represent a monovalent anion.

## Claims

### Claim 1

An organic compound of Formula (1),
wherein, in Formula (1), R1 is an alkyl group or an alkoxy group, X1 and X2 are each independently selected from an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, and A1− and A2− are each independently a monovalent anion.

### Claim 2 (depends on 1)

The organic compound according to claim 1, wherein a reduction of the organic compound produces a reduced state which is colored and which reduced state has an absorption peak in a wavelength band of 630 nm or more and 750 nm or less.

### Claim 3 (depends on 1)

The organic compound according to claim 1, wherein, in Formula (1), R1 is an alkyl group having from 1 to 8 carbon atoms.

### Claim 4 (depends on 1)

The organic compound according to claim 1, wherein, in Formula (1), R1 is an alkoxy group having from 1 to 8 carbon atoms.

### Claim 5 (depends on 1)

The organic compound according to claim 1, wherein, in Formula (1), X1 and X2 are each independently an alkyl group which may have a substituent or an aryl group which may have a substituent.

### Claim 6 (depends on 1)

The organic compound according to claim 1, wherein the organic compound is an electrochromic compound a color tone of which is changed by a redox reaction.

### Claim 7 (depends on 1)

The organic compound according to claim 1, wherein the A1− and the A2− are same anions.

### Claim 8

An electrochromic compound, for use as an electrochromic element, of Formula (1),
wherein, in Formula (1), R1 is an alkyl group or an alkoxy group, X1 and X2 are each independently selected from an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, and A1− and A2− are each independently a monovalent anion.

### Claim 9 (depends on 1)

An electrochromic element comprising:
a pair of electrodes; and
an electrochromic layer disposed between the pair of electrodes, wherein
the electrochromic layer contains the organic compound according to claim 1.

### Claim 10 (depends on 9)

The electrochromic element according to claim 9, wherein the electrochromic layer further contains another kind of organic compounds that is different from the organic compound.

### Claim 11 (depends on 10)

The electrochromic element according to claim 10, wherein the another kind of organic compounds is any one of a phenazine compound, ferrocene, a metallocene compound, a phenylenediamine compound, and a pyrazoline compound.

### Claim 12 (depends on 9)

The electrochromic element according to claim 9, wherein the electrochromic layer is liquid having an electrolyte and the organic compound.

### Claim 13 (depends on 9)

An optical filter comprising:
the electrochromic element according to claim 9; and
an active element connected to the electrochromic element.

### Claim 14 (depends on 13)

The optical filter according to claim 13, wherein the active element adjusts an amount of light passing through the electrochromic element by driving the electrochromic element.

### Claim 15 (depends on 13)

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

### Claim 16 (depends on 13)

An imaging device comprising:
an imaging optical system having a plurality of lenses;
the optical filter according to claim 13; and
an imaging element receiving light passing through the optical filter.

### Claim 17 (depends on 13)

An imaging device, to which an imaging optical system having a plurality of lenses is attachable, the imaging device comprising:
the optical filter according to claim 13; and
an imaging element receiving light passing through the optical filter.

### Claim 18 (depends on 9)

A window component comprising:
a pair of substrates;
the electrochromic element according to claim 9 disposed between the pair of substrates; and
an active element connected to the electrochromic element, wherein
the electrochromic element adjusts an amount of light passing through the pair of substrates.