# US 11,029,575 B2 · Single component electrochromic device having a tunable IR filter

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- Number: US 11,029,575 B2
- Document ID: US11029575B2
- Status: Granted
- Kind: B2
- Application number: 16/235,811
- Filed: 2018-12-28
- Published: 2019-07-04
- Granted: 2021-06-08
- Earliest claimed: 2017-12-29
- Assignees: Gentex Corporation
- Applicants: Gentex Corporation
- Inventors: Punam Giri
- Web page: https://patentgrep.com/patent/US11029575B2

## CPC

- G02F 1/157: Structural association of cells with optical devices, e.g. reflectors or illuminating devices
- C09K 9/02: Organic tenebrescent materials
- G02F 1/15: based on an electrochromic effect
- G02F 1/1516: comprising organic material
- C09K 2211/1051: with sulfur
- G02F 2001/1502: {complementary cell}
- G02F 2001/15145: {the electrochromic layer comprises a mixture of anodic and cathodic 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
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

An electro-optic cell for an electrochromic device includes an electrochromic medium including an electrochromic compound M having at least one reduced state and at least one oxidized state. The electrochromic compound M can act as both the anodic material and the cathodic material in the electro-optic cell. The electrochromic medium can be capable of reversibly attenuating transmittance of light having a wavelength within a predetermined range.

## Claims

### Claim 1

An electro-optic cell, comprising:
an anodic surface and a cathodic surface;
an electrochromic medium including an electrochromic compound M acting as both an anodic material and a cathodic material, wherein the electrochromic compound M includes at least one reduced state and at least one oxidized state; and
wherein the electrochromic medium is capable of reversibly attenuating transmittance of light having a wavelength within a predetermined range, and
wherein the electrochromic compound M comprises a compound of Formula (I):
wherein:
R1 and R2 are individually alkyl, aryl, alkoxy, or aryloxy;
R3, R4, R5, R6, R2, R8 are individually H, alkyl, alkenyl, aryl, alkoxy, or aryloxy;
R9 and R19 are individually H, alkyl, aryl, alkoxy, or aryloxy, or where R1 and R2 are alkyl, R9 and R19 are individually H, alkyl, alkoxy, or aryloxy;
R11 and R12 are individually alkyl, (CH2CH2O)nOCH3, or (CH2)nN*(R20)3[X], wherein n is from 1 to 20;
each R20 is individually alkyl; and
X is an anion.

### Claim 2 (depends on 1)

The electro-optic cell of claim 1, wherein the compound of Formula (I) is reduced to form the species of Formula (II):
and
the compound of Formula (I) is oxidized to form the species of Formula (III):

### Claim 3 (depends on 1)

The electro-optic cell of claim 1, wherein X is F−, Cl−, Br−, I−, BF4, PF6−, SbF6−, AsF6−, Cl4−, SO3CF3−, N(CN)2−, N(CF3SO2)2−, C(CF3SO2)3−, N(SO2C2F5)2−, Al(OC(CF3)3)4−or BAr4−, wherein Ar is an aryl or fluorinated aryl group.

### Claim 4 (depends on 1)

The electro-optic cell of claim 1, wherein the electrochromic medium is selectively reversible between a substantially transparent state and a substantially opaque state with respect to the light having a wavelength within a predetermined range.

### Claim 5 (depends on 1)

The electro-optic cell of claim 1, wherein the predetermined range comprises at least a portion of a range of wavelengths between about 700 nm to about 1400 nm.

### Claim 6 (depends on 1)

The electro-optic cell of claim 1, further comprising a chamber defined at least in part by the anodic surface and the cathodic surface, and wherein the electrochromic medium is disposed within the chamber and electrically coupled with both the anodic surface and the cathodic surface.

### Claim 7 (depends on 1)

A device including the electro-optic cell of claim 1, wherein said device is selected from at least one of a window, an aircraft transparency, a mirror, a display device, a light filter, a camera filter, a watch, eyeglasses, sunglasses, sun visors, and digital billboards.

### Claim 8 (depends on 1)

The electro-optic cell of claim 1, wherein the electrochromic compound M comprises 3,10-dimethoxy-7,14-(4-triethyl ammonium butyl) triphenodithiazine.

### Claim 9

A non-segregated one-component electrochromic device, comprising:
an anodic surface and a cathodic surface;
a chamber defined at least in part by the anodic surface and the cathodic surface; and
an electrochromic medium disposed within the chamber, the electrochromic medium including an anodic material and a cathodic material comprising an electrochromic compound M that is reversibly oxidizable to at least one oxidized state and reversibly reducible to at least one reduced state, and
wherein the electrochromic compound M comprises a compound of Formula (I):
wherein:
R1 and R2 are individually alkyl, aryl, alkoxy, or aryloxy;
R3, R4, R5, R6, R7, R8 are individually H, alkyl, alkenyl, aryl, alkoxy, or aryloxy;
R9 and R10 are individually H, alkyl, aryl, alkoxy, or aryloxy, or where R1 and R2 are alkyl, R9 and R10 are individually H, alkyl, alkoxy, or aryloxy;
R11 and R12 are individually alkyl, (CH2CH2O)nOCH3, or (CH2)nN*(R20)3[X], wherein n is from 1 to 20;
each R20 is individually alkyl; and
X is an anion.

### Claim 10 (depends on 9)

The non-segregated one-component electrochromic device of claim 9, wherein the compound of Formula (I) is reducible to the species of Formula (II):
and
the compound of Formula (I) is oxidizable to the species of Formula (III):

### Claim 11 (depends on 9)

The non-segregated one-component electrochromic device of claim 9, wherein at least one of the oxidation states of the electrochromic compound M has an absorption spectrum that includes light having a wavelength within the range of about 700 nm to about 1400 nm.

### Claim 12 (depends on 11)

The non-segregated one-component electrochromic device of claim 11, wherein the electrochromic medium is substantially transparent to light having a wavelength within the range of about 390 nm to less than about 700 nm.

### Claim 13 (depends on 9)

The non-segregated one-component electrochromic device of claim 9, wherein the electrochromic medium is capable of reversibly attenuating transmittance of light having a wavelength within a predetermined range.

### Claim 14 (depends on 13)

The non-segregated one-component electrochromic device of claim 13, wherein the electrochromic medium is selectively reversible between a substantially transparent state and a substantially opaque state with respect to the light having a wavelength within a predetermined range.

### Claim 15 (depends on 9)

The non-segregated one-component electrochromic device of claim 9, wherein the electrochromic compound M comprises a compound of Formula (IV):

### Claim 16 (depends on 9)

The non-segregated one-component electrochromic device of claim 9, wherein the electrochromic compound M comprises 3,10-dimethoxy-7,14-(4-triethyl ammonium butyl) triphenodithiazine.

### Claim 17

An electrochromic medium for use in an electrochromic device, comprising:
an electrochromic compound of Formula (I):
wherein the electrochromic compound of Formula (I) can be reversibly reduced to form a reduced species of Formula (II):
and
wherein the electrochromic compound of Formula (I) can be reversibly oxidized to form an oxidized species of Formula (III):
wherein:
R1 and R2 individually alkyl, aryl, alkoxy, or aryloxy;
R3, R4, R5, R6, R7, R8 are individually H, alkyl, alkenyl, aryl, alkoxy, or aryloxy;
R9 and R10 are individually H, alkyl, aryl, alkoxy, or aryloxy, or where R1 and R2 alkyl, R9 and R10 are individually H, alkyl, alkoxy, or aryloxy;
R11 and R12 are individually alkyl, (CH2CH2O)nOCH3, or (CH2)nN+(R20)3[X], wherein n is from 1 to 20;
each R20 is individually alkyl; and
X is an anion.

### Claim 18 (depends on 17)

The electrochromic medium of claim 17, wherein at least one of the oxidation states of the electrochromic compound of Formula (I) does not significantly absorb light in a visible wavelength range from about 390 nm to about 700 nm.

### Claim 19 (depends on 17)

The electrochromic medium of claim 17, wherein the electrochromic medium is selectively reversible between a substantially transparent state and a substantially opaque state with respect to light having a wavelength within a range of about 700 nm to about 1400 nm.

### Claim 20 (depends on 17)

The electrochromic medium of claim 17, wherein the electrochromic compound includes a compound of Formula (IV):