Organic electrolytic solution and lithium battery using the same

Patent metadata

Field	Value
Publication number	US-10320032-B2
Application number	US-201715459672-A
Country	US
Kind code	B2
Filing date	Mar 15, 2017
Priority date	Mar 18, 2016
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

Provided is an organic electrolyte solution that includes a lithium salt, an organic solvent, and a sulfonate ester-based compound represented by Formula 1:

R 2 —O—S(═O) 2 —R 1   <Formula 1>
wherein, in Formula 1, R 1 may be a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and R 2 may be a substituted or unsubstituted cyclic sulfone group.

First claim

What is claimed is:

1. An organic electrolyte solution, comprising:
a lithium salt;
an organic solvent; and
a sulfonate ester-based compound represented by Formula 1,
R 2 —O—S(═O) 2 —R 1   <Formula 1>

wherein, in Formula 1,
R 1 is a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and
R 2 is represented by Formula 2:

wherein, in Formula 2,
R 3 and R 4 are each independently hydrogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, or a polar functional group having at least one heteroatom,
n is an integer selected from 4 to 9, and
* represents the R 2 -oxygen bond in Formula 2,
provided that at least one of R 3 and R 4 is a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, or a polar functional group having at least one heteroatom.

2. The organic electrolyte solution as claimed in claim 1 , wherein:
at least one of R 3 and R 4 is the polar functional group having at least one heteroatom, and
the polar functional group having at least one heteroatom includes at least one selected from —F, —Cl, —Br, —I, —C(═O)OR 16 , —OC(═O)OR 16 , —R 15 OC(═O)OR 16 , —C(═O)R 16 , —R 15 C(═O)R 16 , —OC(═O)R 16 , —R 15 OC(═O)R 16 , —C(═O)—O—C(═O)R 16 , —R 15 C(═O)—O—C(═O)R 16 , —SR 16 , —R 15 SR 16 , —SSR 16 , —R 15 SSR 16 , —S(═O)R 16 , —R 15 S(═O)R 16 , —R 15 C(═S)R 16 , —R 15 C(═S)SR 16 , —R 15 SO 3 R 16 , —SO 3 R 16 , —NNC(═S)R 16 , —R 15 NNC(═S)R 16 , —R 15 N═C═S, —NCO, —R 15 —NCO, —NO 2 , —R 15 NO 2 , —R 15 SO 2 R 6 , —SO 2 R 16 ,

wherein R 11 and R 15 are each independently a C1-C20 alkylene group that is unsubstituted or substituted with halogen, a C2-C20 alkenylene group that is unsubstituted or substituted with halogen, a C2-C20 alkynylene group that is unsubstituted or substituted with halogen, a C3-C12 cycloalkylene group that is unsubstituted or substituted with halogen, a C6-C40 arylene group that is unsubstituted or substituted with halogen, a C2-C40 heteroarylene group that is unsubstituted or substituted with halogen, a C7-C15 alkylarylene group that is unsubstituted or substituted with halogen, or a C7-C15 aralkylene group that is unsubstituted or substituted with halogen, and
R 12 , R 13 , R 14 , and R 16 are each independently hydrogen, a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C3-C12 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, a C7-C15 alkylaryl group that is unsubstituted or substituted with halogen, a C7-C15 trialkylsilyl group that is unsubstituted or substituted with halogen, or a C7-C15 aralkyl group that is unsubstituted or substituted with halogen.

3. The organic electrolyte solution as claimed in claim 1 , wherein R 2 is a substituted or unsubstituted sulfolanyl group.

4. The organic electrolyte solution as claimed in claim 3 , wherein:
the sulfolanyl group is substituted, and
the substituent of the sulfolanyl group is a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, or a polar functional group having at least one heteroatom.

5. The organic electrolyte solution as claimed in claim 1 , wherein the sulfonate ester-based compound of Formula 1 is represented by Formula 3 or Formula 4,

wherein, in Formula 3 and Formula 4,
R a and R i are each independently a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and
R b , R c , R d , R e , R f , R g , and R h are each independently hydrogen, a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C1-C20 alkoxy group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen.

6. The organic electrolyte solution as claimed in claim 5 , wherein R a and R i are each independently F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group, and R b , R c , R d , R e , R f , R g , and R h are each independently hydrogen, F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group.

7. The organic electrolyte solution as claimed in claim 1 , wherein the sulfonate ester-based compound of Formula 1 is represented by Formula 5 or Formula 6,

wherein, in Formula 5 and Formula 6,
R j and R m , are each independently a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and
R k and R l are each independently hydrogen, a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that

Assignees

• Samsung Sdi Co Ltd

Inventors

• Kim Aeran
• Son Miyoung
• Choi Hyunbong
• Woo Myungheui
• Lee Seungtae
• Lee Harim
• Goh Aehui
• Shin Woocheol

Classifications

• H01M2300/0037

  Mixture of solvents · CPC title

• H01M2300/0025

  Organic electrolyte · CPC title

• C07D333/48

  by oxygen atoms · CPC title

• H01M10/0567 Primary

  characterised by the additives · CPC title

• H01M10/0568

  characterised by the solutes · CPC title