Electrode active material comprising quinodimethane derivatives, and derivatives, and secondary battery comrising the same

Patent metadata

Field	Value
Publication number	US-2017288228-A1
Application number	US-201715460711-A
Country	US
Kind code	A1
Filing date	Mar 16, 2017
Priority date	Mar 31, 2016
Publication date	Oct 5, 2017
Grant date	—

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.

First claim

What is claimed is:

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.

2 . The electrode active material of claim 1 , wherein the quinodimethane compound is a compound represented by Formula 1:

wherein, in Formula 1,
Ar 1 to Ar a are each independently a substituted or unsubstituted C 5 -C 60 carbocyclic group, or a substituted or unsubstituted C 1 -C 60 heterocyclic group;
R a to R h 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group;
n is an integer of 1 or greater;
at least one substituent of each of the substituted C 5 -C 60 carbocyclic group and the substituted C 1 -C 60 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 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 C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)( Q21 )( Q22 ), and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ),
wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

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

4 . The electrode active material of claim 2 , wherein Ar 1 to Ar 3 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), wherein Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

5 . 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,
R a to R h 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group,
at least one selected from R a to R h is a cyano group,
R 1 to R 6 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, and n is an integer of 1 or greater.

6 . The electrode active material of claim 2 , wherein the quinodimethane compound is a compound represented by Formula 1A-1:

wherein, in Formula 1A-1, R 1 to R 6 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, and
n is an integer of 1 or greater.

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

Assignees

• Samsung Electronics Co Ltd
• Univ Mie

Inventors

• Ito Seitaro
• Mizumo Tomonobu
• Aihara Yuichi
• Itoh Takahito
• Uno Takahiro

Classifications

• H01M2300/0034

  Fluorinated solvents · CPC title

• H01M10/0525

  Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries · CPC title

• H01M4/60 Primary

  of organic compounds · CPC title

• H01M4/382

  Lithium (H01M4/405 takes precedence) · CPC title

• H01M2300/0082

  Organic polymers · CPC title