IP Library Granted Patent US 9,912,010
Granted Patent B2
US 9,912,010 · App. 14/788,414 · Granted Mar 6, 2018

Electrolytic solution for lithium battery and lithium battery using the same

Inventors: Siyoung Cha (Yongin-si, KR); Myungheui Woo (Yongin-si, KR); Seonghun Jeong (Yongin-si, KR); Woocheol Shin (Yongin-si, KR)
Assignee: Samsung SDI Co., Ltd.
H01M10/0567H01M4/587H01M10/0525H01M2300/0025
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Quick Facts
Patent No.
US 9,912,010
App. No.
14/788,414
Granted
Mar 6, 2018
Kind
B2
Abstract

An electrolytic solution for a lithium battery includes a lithium salt, an organic solvent; a disultone-based compound represented by Formula 1, and a non-polar unsaturated group-containing cyclic carbonate-based compound: wherein, in Formula 1, A 1 to A 4 are each independently a substituted or unsubstituted C 1 -C 5 alkylene group, a carbonyl group, or a sulfinyl; n1 to n4 are each independently an integer 1 to 3, and when n1 to n4 are each independently two or greater, a respective plurality of any of A 1 s to A 4 s are identical to or different from each other. When the lithium battery includes the electrolyte solution, room-temperature and high-temperature lifespan characteristics of the lithium battery may improve.

Claims (38)

1. An electrolytic solution for a lithium battery, the electrolytic solution comprising:

a lithium salt;

an organic solvent;

a non-polar unsaturated group-containing cyclic carbonate-based compound; and

a disultone-based compound represented by Formula 1:

wherein, in Formula 1,

A 1 to A 4 are each independently selected from a substituted or unsubstituted C 1 -C 5 alkylene group, a carbonyl group, and a sulfinyl group;

n1 to n4 are each independently an integer selected from 1 to 3; and

when n1 to n4 are each independently two or greater, the respective plurality of any of A 1 s to A 4 s are identical to or different from each other.

2. The electrolytic solution of claim 1 , wherein at least one of A 1 to A 4 is a substituted C 1 -C 5 alkylene group, and the substituent is at least one selected from a deuterium atom, a halogen substituted or unsubstituted C 1 -C 20 alkyl group, a halogen substituted or unsubstituted C 5 -C 20 cycloalkyl group, a halogen substituted or unsubstituted C 1 -C 20 alkoxy group, a halogen substituted or unsubstituted C 2 -C 20 alkenyl group, a halogen substituted or unsubstituted C 2 -C 20 alkynyl group, a halogen substituted or unsubstituted C 3 -C 20 cycloalkenyl group, a halogen substituted or unsubstituted C 3 -C 20 heterocycloalkyl group, a halogen substituted or unsubstituted C 1 -C 20 heterocycloalkenyl group, a halogen substituted or unsubstituted C 6 -C 40 aryl group, a halogen substituted or unsubstituted C 3 -C 40 aryloxy group, a halogen substituted or unsubstituted C 3 -C 40 arylthio group, a halogen substituted or unsubstituted C 2 -C 40 heteroaryl group, and a polar functional group comprising a heteroatom in addition to any of the substituents above.

3. The electrolytic solution of claim 2 , wherein the polar functional group comprising a heteroatom is selected from —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a thiocyano group, an isocyanato group, a nitro group, a nitroso group, an azide group, an amino group, an amidino group, a hydrazine group, a hydrazone group, —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 , —NNC(═S)R 16 , —R 15 NNC(═S)R 16 ,

R 11 and R 15 are each independently selected from a halogen substituted or unsubstituted C 1 -C 20 alkylene group, a halogen substituted or unsubstituted C 2 -C 20 alkenylene group, a halogen substituted or unsubstituted C 3 -C 20 cycloalkylene group, a halogen substituted or unsubstituted C 3 -C 20 cycloalkenylene group, a halogen substituted or unsubstituted C 1 -C 20 heterocycloalkenylene group, a halogen substituted or unsubstituted C 6 -C 20 arylene group, and a halogen substituted or unsubstituted C 1 -C 20 heteroarylene group; and

R 12 , R 13 , R 14 , and R 16 are each independently selected from a hydrogen atom, a halogen atom, a halogen substituted or unsubstituted C 1 -C 20 alkyl group, a halogen substituted or unsubstituted C 2 -C 20 alkenyl group, a halogen substituted or unsubstituted C 2 -C 20 alkynyl group, a halogen substituted or unsubstituted C 2 -C 20 alkoxy group, a halogen substituted or unsubstituted C 3 -C 20 cycloalkyl group, a halogen substituted or unsubstituted C 1 -C 20 heterocycloalkyl group, a halogen substituted or unsubstituted C 3 -C 20 cycloalkenyl group, a halogen substituted or unsubstituted C 1 -C 20 heterocycloalkenyl group, a halogen substituted or unsubstituted C 6 -C 20 aryl group, a halogen substituted or unsubstituted C 6 -C 20 aryloxy group, a halogen substituted or unsubstituted C 5 -C 20 arylthio group, a halogen substituted or unsubstituted C 2 -C 40 heteroaryl group, and a halogen substituted or unsubstituted C 7 -C 15 trialkylsilyl group.

4. The electrolytic solution of claim 3 , wherein the halogen atom is fluorine.

5. The electrolytic solution of claim 1 , wherein at least one of A 1 to A 4 is a substituted C 1 -C 5 alkylene group, and the substituent is at least one selected from a halogen atom, 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, and a pyridinyl group.

6. The electrolytic solution of claim 1 , wherein A 1 to A 4 are each independently a C 1 -C 5 alkylene group, n1 and n3 are each independently selected from 1 and 2, and n2 and n4 are each independently 1.

7. The electrolytic solution of claim 1 , wherein the disultone-based compound is represented by at least one of Formulae 2 and 3:

wherein, in Formulae 2 and 3,

B 1 to B 4 and D 1 to D 6 are each independently selected from —C(E 1 )(E 2 )-, a carbonyl group, and a sulfinyl group; and

E 1 and E 2 are each independently selected from a hydrogen atom, a halogen atom, a halogen substituted or unsubstituted C 1 -C 20 alkyl group, a halogen substituted or unsubstituted C 2 -C 20 alkenyl group, a halogen substituted or unsubstituted C 2 -C 20 alkynyl group, a halogen substituted or unsubstituted C 2 -C 20 alkoxy group, a halogen substituted or unsubstituted C 3 -C 20 cycloalkyl group, a halogen substituted or unsubstituted C 1 -C 20 heterocycloalkyl group, a halogen substituted or unsubstituted C 3 -C 20 cycloalkenyl group, a halogen substituted or unsubstituted C 1 -C 20 heterocycloalkenyl group, a halogen substituted or unsubstituted C 6 -C 20 aryl group, a halogen substituted or unsubstituted C 6 -C 20 aryloxy group, a halogen substituted or unsubstituted C 5 -C 20 arylthio group, and a halogen substituted or unsubstituted C 2 -C 40 heteroaryl group.

8. The electrolytic solution of claim 7 , wherein E 1 and E 2 are each independently selected from a hydrogen atom, a halogen atom, 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, and a pyridinyl group.

9. The electrolytic solution of claim 7 , wherein E 1 and E 2 are each independently selected from a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, a trifluoromethyl group, a tetrafluoroethyl group, and a phenyl group.

10. The electrolytic solution of claim 1 , wherein the disultone-based compound is represented by at least one of Formulae 4 and 5:

wherein, in Formulae 4 and 5,

R 1 to R 8 and R 21 to R 32 are each independently selected from a hydrogen atom, a halogen atom, a halogen substituted or unsubstituted C 1 -C 10 alkyl group, a halogen substituted or unsubstituted C 6 -C 20 aryl group, and a halogen substituted or unsubstituted C 1 -C 20 heteroaryl group.

11. The electrolytic solution of claim 10 , wherein R 1 to R 8 and R 21 to R 32 are each independently selected from a hydrogen atom, a halogen atom, 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, and a pyridinyl group.

12. The electrolytic solution of claim 10 , wherein R 1 to R 8 and R 21 to R 32 are each independently selected from a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a tetrafluoroethyl group, and a phenyl group.

13. The electrolytic solution of claim 1 , wherein the disultone-based compound is represented by at least one of Formulae 6 to 17:

14. The electrolytic solution of claim 1 , wherein the non-polar unsaturated group-containing cyclic carbonate-based compound comprises a vinyl group, a vinylene group, or a non-polar unsaturated group of a combination thereof.

15. The electrolytic solution of claim 1 , wherein the non-polar unsaturated group-containing cyclic carbonate-based compound is at least one selected from vinylene carbonate; a vinylene carbonate derivative having at least one substituent selected from a halogen atom, a cyano group (CN), and a nitro group (NO 2 ); vinylethylene carbonate; and a vinylethylene carbonate derivative having at least one substituent selected from a halogen atom, a cyano group (CN), and a nitro group (NO 2 ).

16. The electrolytic solution of claim 1 , wherein the non-polar unsaturated group-containing cyclic carbonate-based compound is at least one selected from vinylene carbonate and vinylethylene carbonate.

17. The electrolytic solution of claim 1 , wherein an amount of the disultone-based compound and an amount of the non-polar unsaturated group-containing cyclic carbonate-based compound are each independently in a range of about 0.1 wt % to about 10 wt % based on the total weight of the electrolytic solution.

18. A lithium battery comprising:

a positive electrode;

a negative electrode; and

the electrolytic solution of claim 1 .

19. The lithium battery of claim 18 , wherein the negative electrode comprises graphite.

20. The lithium battery of claim 18 , wherein the lithium battery has a driving voltage of 3.8 V or greater.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2015
From: CHA, SIYOUNG; WOO, MYUNGHEUI; JEONG, SEONGHUN; SHIN, WOOCHEOL
To: SAMSUNG SDI CO., LTD.
Reel/Frame 036102/0358 →
Priority Claims (1)
KR 10-2015-0008252 · Jan 16, 2015 · national
Continuity (1)
Related Publication 20160211550A1 · Jul 21, 2016