# US 2021/0240047 A1 · Electrochromic compounds

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- Number: US 2021/0240047 A1
- Document ID: US20210240047A1
- Status: Published application
- Kind: A1
- Application number: 17/166,079
- Filed: 2021-02-03
- Published: 2021-08-05
- Earliest claimed: 2020-02-05
- Assignees: Gentex Corporation
- Applicants: Gentex Corporation
- Inventors: Punam Giri
- Web page: https://patentgrep.com/patent/US20210240047A1

## CPC

- C09K 9/02: Organic tenebrescent materials
- G02F 1/1503: caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
- G02F 1/1516: comprising organic material
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1025: characterised by ligands
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- G02F 1/155: Electrodes
- G02F 2202/02: organic material
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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

## Abstract

An anodic redox species and a device using the chemical compound are disclosed. The device may comprise a first substrate, a second substrate, a first electrode, a second electrode, and/or an electrochromic medium. The second substrate may be disposed in a spaced apart relationship with the first substrate. The first electrode may be associated with the first substrate. The second electrode may likewise associated with the second substrate. The electrochromic medium may be disposed between the first and second electrodes. Further, the electrochromic medium may comprise at least one anodic redox species and at least one cathodic redox species. Lastly, the anodic redox species is a species of a formula whose compounds may have improved oxidation potentials.

## Claims

### Claim 1

A device comprising:
a first substrate;
a second substrate disposed in a spaced apart relationship with the first substrate;
a first electrode associated with the first substrate;
a second electrode associated with the second substrate;
an electrochromic medium disposed between the first and second electrodes, wherein the electrochromic medium comprises at least one anodic redox species and at least one cathodic redox species, and the anodic redox species is of a first formula:
wherein:
R5 and R10 are each a poly substituted ammonium group, and
R1-R4 and R6-R9 are each individually one of:
from the group consisting of: H, F, Cl, Br, I, CN, OR11, NO2, alkyl, alkoxy aryl, or amino, wherein R11 is an H or alkyl group, and
joining any adjacent R of R1-R4 and R6-R9 to form at least one of a monocyclic, polycyclic, and heterocyclic group.

### Claim 2 (depends on 1)

The device of claim 1, wherein the anodic redox species is also of a second formula:

### Claim 3 (depends on 2)

The device of claim 2, wherein the anodic redox species is N,N-(phenazine-5,10-diylbis(ethane-2,1-diyl))bis(3-hydroxy-N,N-dimethylpropan-1-aminium).

### Claim 4 (depends on 1)

The device of claim 1, wherein the anodic redox species is also of a fourth formula:

### Claim 5 (depends on 4)

The device of claim 4, wherein the anodic redox species is 2,2′-(phenazine-5,10-diyl) bis(N,N,N-triethylethan-1-aminium).

### Claim 6 (depends on 1)

The device of claim 1, wherein:
the anodic redox species has a first oxidation potential;
the electrochromic medium further comprises an electrochromic species having a first oxidation potential and a second oxidation potential; and
the first oxidation potential of the anodic redox species is greater than the first oxidation potential of the electrochromic species and less than the second oxidation potential of the electrochromic species.

### Claim 7

A device comprising:
a first substrate;
a second substrate disposed in a spaced apart relationship with the first substrate;
a first electrode associated with the first substrate;
a second electrode associated with the second substrate;
an electrochromic medium disposed between the first and second electrodes; wherein the electrochromic medium comprises at least one anodic redox species and at least one cathodic redox species, and the anodic redox species is of a first formula:
wherein:
R5 and R10 are each any alkyl group,
at least one of R1-R4 and R6-R9 is a poly substituted ammonium group, wherein the poly substituted ammonium group is substituted with a combination selected from the group consisting of: H, F, Cl, Br, I, CN, OR11, NO2, alkyl, alkoxy aryl, ammonium, fluoroalkyl, or amino, wherein R11 is an H or alkyl group, and
each of the remaining of R1-R4 and R6-R9 are one of:
from the group consisting of: H, F, Cl, Br, I, CN, OR11, NO2, alkyl, alkoxy aryl, ammonium, fluoroalkyl, or amino, wherein R11 is an H or alkyl group, and
joining any adjacent R of R1-R4 and R6-R9 to form at least one of a monocyclic, polycyclic, and heterocyclic group.

### Claim 8 (depends on 7)

The device of claim 7, wherein two of R1-R4 and R6-R9 are poly substituted ammonium groups.

### Claim 9 (depends on 8)

The device of claim 8, wherein one of the substituents of the poly substituted ammonium groups is a propyl alcohol group.

### Claim 10 (depends on 9)

The device of claim 9, wherein the anodic redox species is also of a second formula: N2,N7-bis(3-hydroxypropyl)-N2,N2,N7,N7-tetramethyl-5,10-dineopentyl-5,10-dihydrophenazine-2,7-diaminium.

### Claim 11 (depends on 7)

The device of claim 7, wherein at least one of R2 and R7 are a poly substituted ammonium group, a cyano group, or a fluoroalkyl group.

### Claim 12 (depends on 11)

The device of claim 11, wherein the alkyl groups of R5 and R10 are a butyl alcohol.

### Claim 13 (depends on 12)

The device of claim 12, wherein the anodic redox species is also of a second formula:

### Claim 14 (depends on 13)

The device of claim 13, wherein three of the substituents of the poly substituted ammonium group are alkyl groups.

### Claim 15 (depends on 14)

The device of claim 14, wherein the alkyl groups are a alkyl hydroxy chain.

### Claim 16 (depends on 13)

The device of claim 13, wherein at least one of R2 and R7 are a cyano group.

### Claim 17 (depends on 16)

The device of claim 16, wherein the anodic redox species is 5,10-bis(4hydroxybutyl)-5,10-dihyrophenazin-2-carbonitrile.

### Claim 18 (depends on 13)

The device of claim 13, wherein at least one of R2 and R7 are a fluoroalkyl group.

### Claim 19 (depends on 18)

The device of claim 18, wherein the anodic redox species is 4,4′-(2-(trifluoromethyl)phenazine-5,10-diyl)bis(butan-1-ol).

### Claim 20 (depends on 7)

The device of claim 7, wherein:
the anodic redox species has a first oxidation potential;
the electrochromic medium further comprises an electrochromic species having a first oxidation potential and a second oxidation potential; and
the first oxidation potential of the anodic redox species is greater than the first oxidation potential of the electrochromic species and less than the second oxidation potential of the electrochromic species.