IP Library Granted Patent US 10,320,032
Granted Patent B2
US 10,320,032 · App. 15/459,672 · Granted Jun 11, 2019

Organic electrolytic solution and lithium battery using the same

Inventors: AeRan Kim (Yongin-si, KR); MiYoung Son (Yongin-si, KR); HyunBong Choi (Yongin-si, KR); MyungHeui Woo (Yongin-si, KR); SeungTae Lee (Yongin-si, KR); HaRim Lee (Yongin-si, KR); AeHui Goh (Yongin-si, KR); WooCheol Shin (Yongin-si, KR)
Assignee: Samsung SDI Co., Ltd.
H01M10/0567C07D327/04C07D333/48H01M10/052H01M10/0568H01M2300/0025H01M2300/0037
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Quick Facts
Patent No.
US 10,320,032
App. No.
15/459,672
Granted
Jun 11, 2019
Kind
B2
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.

Claims (48)

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 is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen.

8. The organic electrolyte solution as claimed in claim 7 , wherein R j and R m 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 k and R l 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.

9. The organic electrolyte solution as claimed in claim 1 , wherein an amount of the sulfonate ester-based compound is in a range of about 0.01 wt % to about 10 wt % based on the total weight of the organic electrolyte solution.

10. The organic electrolyte solution as claimed in claim 1 , wherein the lithium salt in the organic electrolyte solution includes at least one selected from LiPF 6 , LiBF 4 , LiSbF 6 , LiAsF 6 , LiClO 4 , LiCF 3 SO 3 , Li(CF 3 SO 2 ) 2 N, LiC 4 F 9 SO 3 , LiAlO 2 , LiAlCl 4 , LiN(C x F 2x+1 SO 2 )(C y F 2y+1 SO 2 ) (where 2≤x≤20 and 2≤y≤20), LiCl, and LiI.

11. An organic electrolyte solution, comprising:

a lithium salt;

an organic solvent; and

a sulfonate ester-based compound represented by one of the following Formulae 8 to 14, 16 18 to 22:

12. A lithium battery, comprising:

a cathode,

an anode, and

the organic electrolyte solution as claimed in claim 1 .

13. The lithium battery as claimed in claim 12 , wherein the cathode includes a lithium transition metal oxide having a nickel-containing layered structure.

14. The lithium battery as claimed in claim 12 , wherein the lithium battery has a voltage of about 3.8 V or higher.

15. A lithium battery, comprising:

a cathode,

an anode, and

the organic electrolyte solution as claimed in claim 11 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2017
From: KIM, AERAN; SON, MIYOUNG; CHOI, HYUNBONG; WOO, MYUNGHEUI; LEE, SEUNGTAE; LEE, HARIM; GOH, AEHUI; SHIN, WOOCHEOL
To: SAMSUNG SDI CO., LTD.
Reel/Frame 041584/0458 →
Priority Claims (1)
KR 10-2016-0032732 · Mar 18, 2016 · national
Continuity (1)
Related Publication 20170271715A1 · Sep 21, 2017