# US 2017/0288228 A1 · Electrode active material comprising quinodimethane derivatives, and derivatives, and secondary battery comrising the same

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- Number: US 2017/0288228 A1
- Document ID: US20170288228A1
- Status: Published application
- Kind: A1
- Application number: 15/460,711
- Filed: 2017-03-16
- Published: 2017-10-05
- Earliest claimed: 2016-03-31
- Assignees: Samsung Electronics Co., Ltd.; Mie University
- Applicants: Samsung Electronics Co., Ltd.; Mie University
- Inventors: Seitaro ITO; Tomonobu MIZUMO; Yuichi AIHARA; Takahito ITOH; Takahiro UNO
- Web page: https://patentgrep.com/patent/US20170288228A1

## CPC

- C07C 255/34: with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
- H01M 4/606: {containing aromatic main chain polymers}
- H01M 10/052: Li-accumulators
- H01M 10/0562: Solid materials
- H01M 10/0565: Polymeric materials, e.g. gel-type or solid-type
- H01M 2300/0068: inorganic
- H01M 2300/0082: Organic polymers
- Y02E 60/10: Energy storage using batteries
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An electrode active material including at least one selected from a quinodimethane derivative and a lithium salt thereof, wherein the quinodimethane derivative has at least three linearly-condensed aryl groups and at least two quinodimethane moieties.

## Claims

### Claim 1

An electrode active material comprising:
at least one selected from a quinodimethane compound and a lithium salt thereof, wherein the quinodimethane compound comprises at least three linearly-condensed aryl groups and at least two quinodimethane moieties.

### Claim 2 (depends on 1)

The electrode active material of claim 1, wherein the quinodimethane compound is a compound represented by Formula 1:
wherein, in Formula 1,
Ar1 to Ara are each independently a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group;
Ra to Rh are each independently selected from a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxylic acid group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group;
n is an integer of 1 or greater;
at least one substituent of each of the substituted C5-C60 carbocyclic group and the substituted C1-C60 heterocyclic group is selected from deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), -B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22), and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

### Claim 3 (depends on 2)

The electrode active material of claim 2, wherein at least one selected from Ra to Rh is a cyano group.

### Claim 4 (depends on 2)

The electrode active material of claim 2, wherein Ar1 to Ar3 are each independently selected from
a benzene group, a naphthalene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, and a pentaphene group; and
a benzene group, a naphthalene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, naphthacene group, a picene group, a perylene group, and a pentaphene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q31 to Q33 are each independently selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

### Claim 5 (depends on 2)

The electrode active material of claim 2, wherein the quinodimethane compound is a compound represented by Formula 1A or 1B:
wherein, in Formulae 1A and 1B,
Ra to Rh are each independently selected from a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxylic acid group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group,
at least one selected from Ra to Rh is a cyano group,
R1 to R6 are each independently selected from a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxylic acid group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group, and n is an integer of 1 or greater.

### Claim 6 (depends on 2)

The electrode active material of claim 2, wherein the quinodimethane compound is a compound represented by Formula 1A-1:
wherein, in Formula 1A-1, R1 to R6 are each independently selected from a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxylic acid group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group, and
n is an integer of 1 or greater.

### Claim 7 (depends on 6)

The electrode active material of claim 6, wherein n is an integer selected from 1 to 4.

### Claim 8 (depends on 6)

The electrode active material of claim 6, wherein n is 1.

### Claim 9 (depends on 6)

The electrode active material of claim 6, wherein each of R1 to R6 is a hydrogen atom.

### Claim 10 (depends on 1)

The electrode active material of claim 1, wherein the electrode active material comprises about 60 percent by weight or more of the quinodimethane compound based on a total weight of the electrode active material.

### Claim 11 (depends on 1)

The electrode active material of claim 1, wherein the electrode active material comprises about 90 percent by weight or more of the quinodimethane compound based on a total weight of the electrode active material.

### Claim 12 (depends on 1)

The electrode active material of claim 1, wherein the quinodimethane compound has two or more oxidation-reduction potentials in a range of about 1.0 volts to about 4.0 volts with respect to Li/Li+.

### Claim 13 (depends on 12)

The electrode active material of claim 12, wherein the quinodimethane compound has two or more oxidation-reduction potentials in a range of about 2.0 volts to about 3.5 volts with respect to Li/Li+.

### Claim 14 (depends on 1)

The electrode active material of claim 1, wherein the electrode active material is a positive active material.

### Claim 15 (depends on 1)

A secondary battery comprising:
a positive electrode comprising an electrode active material of claim 1;
a negative electrode; and
an electrolyte membrane.

### Claim 16 (depends on 15)

The secondary battery of claim 15, wherein the negative electrode comprises at least one selected from a graphite active material, a silicon oxide or an alloy thereof, a tin oxide or an alloy thereof, a titanium oxide compound, and an alkali metal.

### Claim 17 (depends on 15)

The secondary battery of claim 15, wherein the electrolyte membrane comprises a solid electrolyte or a polymer electrolyte.

### Claim 18 (depends on 17)

The secondary battery of claim 17, wherein the solid electrolyte is a phosphoric acid solid electrolyte.

### Claim 19 (depends on 15)

The secondary battery of claim 15, wherein the secondary battery has a cutoff potential of about 1.8 volts to about 3.8 volts, and a discharge capacity of about 150 milliampere hours per gram or greater after 2 to 4 charge and discharge cycles at about 25° C.

### Claim 20 (depends on 15)

The secondary battery of claim 15, wherein the secondary battery has a cutoff potential of about 1.8 volts to about 3.8 volts, and capacity retention of about 80% or greater after 50 charge and discharge cycles at about 25° C.