# US 10,481,456 B2 · Electrochemical energy storage devices

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- Number: US 10,481,456 B2
- Document ID: US10481456B2
- Status: Granted
- Kind: B2
- Application number: 15/853,420
- Filed: 2017-12-22
- Published: 2018-06-07
- Granted: 2019-11-19
- Earliest claimed: 2014-05-27
- Assignees: Gentex Corporation
- Applicants: Gentex Corporation
- Inventors: David A. Theiste; Leroy J. Kloeppner; Sue F. Franz; Punam Giri; Rongguang Lin
- Web page: https://patentgrep.com/patent/US10481456B2

## CPC

- H01M 4/137: Electrodes based on electro-active polymers
- G02F 1/1506: caused by electrodeposition, e.g. electrolytic deposition of an inorganic material on or close to an electrode
- G02F 1/1525: {characterised by a particular ion transporting layer, e.g. electrolyte}
- H01G 9/02: Diaphragms; Separators
- H01G 9/035: Liquid electrolytes, e.g. impregnating materials (H01G11/54 takes precedence)
- H01G 9/0425: {specially adapted for cathode}
- H01G 9/145: Liquid electrolytic capacitors (H01G11/00 takes precedence)
- H01G 11/04: Hybrid capacitors
- H01G 11/48: Conductive polymers
- H01M 4/366: {as layered products}
- H01M 4/606: {containing aromatic main chain polymers}
- H01M 4/608: {containing heterocyclic rings}
- H01M 4/66: Selection of materials
- H01M 6/18: with solid electrolyte
- H01M 10/05: Accumulators with non-aqueous electrolyte (H01M10/39 takes precedence)
- H01M 10/0567: characterised by the additives
- C07D 241/48: with hydrocarbon radicals, substituted by nitrogen atoms, directly attached to the ring nitrogen atoms
- C07D 279/28: with other substituents attached to the ring system
- G02F 1/1503: caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
- G02F 1/15165: {Polymers}
- G02F 2001/15145: {the electrochromic layer comprises a mixture of anodic and cathodic compounds}
- G02F 2001/1518: {Ferrocene compounds}
- H01G 11/52: Separators
- H01G 11/62: characterised by the solute, e.g. salts, anions or cations therein
- H01M 10/0568: characterised by the solutes
- H01M 10/0569: characterised by the solvents
- H01M 2004/027: {Negative electrodes}
- H01M 2004/028: {Positive electrodes}
- Y02E 60/10: Energy storage using batteries
- Y02E 60/13: Energy storage using capacitors
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- 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
- H01G: CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE (selection of specified materials as dielectric H01B3/00; capacitors having potential barriers H10D1/62, H10K10/10)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An energy storage device includes a cathodic material in an activated state; and an anodic material in an activated state; wherein: the cathodic material is a viologen covalently attached to, or confined within, a first polymer matrix, the first polymer matrix is configured to prevent or minimize substantial diffusion of the cathodic material in the activated state; and the anodic material is a phenazine, a phenothiazine, a triphenodithiazine, a carbazole, a indolocarbazole, a biscarbazole, or a ferrocene covalently attached to, or confined within, a second polymer matrix, the second polymer matrix is configured to prevent or minimize substantial diffusion of the anodic material in the activated state.

## Claims

### Claim 1

A energy storage device comprising:
a cathodic material in an activated state; and
an anodic material in an activated state;
wherein:
the cathodic material is a viologen covalently attached to, or confined within, a first polymer matrix, the first polymer matrix configured to prevent or minimize substantial diffusion of the cathodic material in the activated state;
the anodic material is a phenazine, a phenothiazine, a triphenodithiazine, a carbazole, a indolocarbazole, a biscarbazole, or a ferrocene covalently attached to, or confined within, a second polymer matrix, the second polymer matrix configured to prevent or minimize substantial diffusion of the anodic material in the activated state; and
the energy storage device exhibits an open circuit voltage of about 0.2 V to about 1.2 V.

### Claim 2 (depends on 1)

The energy storage device of claim 1 that exhibits an open circuit voltage of 0.6 V to 0.8 V.

### Claim 3 (depends on 1)

The energy storage device of claim 1 further comprising an electrolyte.

### Claim 4 (depends on 3)

The energy storage device of claim 3, wherein the electrolyte comprises a solvent and a metal salt or an ammonium salt.

### Claim 5

A energy storage device comprising:
a first cell comprising an anodic material in an activated state;
a second cell comprising a cathodic material in an activated state;
a porous separator isolating the first cell from the second cell; and
wherein:
the anodic material is a phenazine, a phenothiazine, a triphenodithiazine, a carbazole, a indolocarbazole, a biscarbazole, or a ferrocene;
the cathodic material is a viologen; and
the energy storage device exhibits an open circuit voltage of about 0.2 V to about 1.2 V.

### Claim 6 (depends on 5)

The energy storage device of claim 5 further comprising an electrolyte comprising a solvent and a metal salt or an ammonium salt.

### Claim 7 (depends on 5)

The energy storage device of claim 5, wherein the separator comprises an ion exchange membrane or a size-exclusion membrane.

### Claim 8 (depends on 5)

The energy storage device of claim 5 which is a battery.

### Claim 9 (depends on 5)

The energy storage device of claim 5 which is a capacitor, or a supercapacitor.

### Claim 10 (depends on 5)

The energy storage device of claim 5, wherein the anodic compound in an activated state is an anion of a compound is represented by:
wherein:
E is S or NR10;
R1 and R10 are individually an alkyl group interrupted by at least one ammonium group;
R2-R9 are individually H, F, Cl, Br, I, CN, OR11, SR11, NO2, alkyl, alkoxy, aryl, amino, or any two adjacent groups of R2-R9 may join to form a monocyclic, polycyclic, or heterocyclic group;
each R11 is individually H or alkyl; and
R12 is an alkylene group.

### Claim 11 (depends on 10)

The energy storage device of claim 10, wherein E is NR10 and R2-R9 are H or OR11.

### Claim 12 (depends on 10)

The energy storage device of claim 10, wherein the anodic compound in an activated state is an anion of a compound is represented by:
wherein:
each R13 is individually H or alkyl;
R14 is an alkyl group interrupted by at least one ammonium group.

### Claim 13 (depends on 12)

The energy storage device of claim 12, wherein R1 and R14 are represented by:
R15-R18 are individually H or alkyl;
n is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12;
n′ is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and
x is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

### Claim 14 (depends on 13)

The energy storage device of claim 13, wherein n is 4, x is 2, and n′ is 11.