IP Library Granted Patent US 10,847,841
Granted Patent B2
US 10,847,841 · App. 16/185,042 · Granted Nov 24, 2020

Electrolyte additive for lithium battery, organic electrolyte solution including the same, and lithium battery including the same

Inventors: Insun Park (Suwon-si, KR); Myongchun Koh (Hwaseong-si, KR); Dongyoung Kim (Yongin-si, KR); Eunha Park (Seoul, KR); Yoonsok Kang (Seongnam-si, KR); Jinah Seo (Seoul, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
H01M10/0567H01M4/366H01M4/386H01M4/505H01M4/525H01M4/587H01M10/0525H01M10/0568H01M10/0569H01M10/4235H01M2300/0025
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Quick Facts
Patent No.
US 10,847,841
App. No.
16/185,042
Granted
Nov 24, 2020
Kind
B2
Abstract

An electrolyte additive for a lithium battery comprising a sulfone compound represented by Formula 1: wherein, in Formula 1, R 1 is a halogen-substituted or unsubstituted C1-C5 alkyl group, a halogen-substituted or unsubstituted C4-C10 cycloalkyl group, a halogen-substituted or unsubstituted C5-C10 aryl group, or a halogen-substituted or unsubstituted C2-C10 heteroaryl group, and R 2 is a halogen-substituted or unsubstituted C2-C10 alkenyl group.

Claims (53)

1. An organic electrolyte solution, comprising:

a lithium salt;

an organic solvent; and

an electrolyte additive for a lithium battery comprising a sulfone compound represented by Formula 1:

wherein, in Formula 1,

R 1 is a halogen-substituted or unsubstituted C1-C5 alkyl group, a halogen-substituted or unsubstituted C4-C10 cycloalkyl group, a halogen-substituted or unsubstituted C5-C10 aryl group, or a halogen-substituted or unsubstituted C2-C10 heteroaryl group, and

R 2 is a halogen-substituted or unsubstituted C2-C10 alkenyl group,

wherein the organic solvent comprises a cyclic carbonate compound represented by Formula 17:

wherein, in Formula 17,

X 1 and X 2 are each independently a hydrogen atom or a halogen atom, and at least one of X 1 and X 2 is fluorine, and

wherein an amount of the cyclic carbonate compound represented by Formula 17 is 10 volume percent or less based on a total volume of the organic solvent.

2. The organic electrolyte solution of claim 1 , wherein the sulfone compound represented by Formula 1 is a sulfone compound represented by Formula 2:

wherein, in Formula 2,

R 3 is a halogen-substituted or unsubstituted C1-C5 alkyl group or a halogen-substituted or unsubstituted C5-C10 aryl group, and

R 4 is a covalent bond, a C1-C5 alkylene group or a C2-C10 alkenylene group.

3. The organic electrolyte solution of claim 1 , wherein the sulfone compound represented by Formula 1 is a compound represented by one of Formulae 3 to 9:

4. The organic electrolyte solution of claim 1 , wherein an amount of the sulfone compound represented by Formula 1 is in a range of about 0.1 weight percent to about 3 weight percent based on the total weight of the organic electrolyte solution.

5. The organic electrolyte solution of claim 1 , wherein the organic solvent comprises a cyclic carbonate compound represented by Formula 17a:

wherein, in Formula 17a,

X 1 is a hydrogen atom and X 2 is fluorine.

6. The organic electrolyte solution of claim 5 , wherein an amount of the cyclic carbonate compound represented by Formula 17a is about 10 volume percent or less based on a total volume of the organic solvent.

7. The organic electrolyte solution of claim 1 , wherein the organic electrolyte solution further comprises a cyclic carbonate compound represented by Formula 18:

wherein, in Formula 18,

X 3 and X 4 are each independently a hydrogen atom, a halogen atom, or a C1-C3 alkyl group.

8. The organic electrolyte solution of claim 7 , wherein an amount of the cyclic carbonate compound represented by Formula 18 is about 3 weight percent or less based on the total weight of the organic electrolyte solution.

9. The organic electrolyte solution of claim 1 , wherein the organic solvent further comprises at least one of ethylmethyl carbonate, methylpropyl carbonate, ethylpropyl carbonate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, propylene carbonate, ethylene carbonate, butylene carbonate, ethyl propionate, ethyl butyrate, acetonitrile, succinonitrile, adiponitrile, dimethyl sulfoxide, dimethyl formamide, dimethyl acetamide, gamma-valerolactone, gamma-butyrolactone, and tetrahydrofuran.

10. The organic electrolyte solution of claim 1 , wherein

the sulfone compound represented by Formula 1 is a compound represented by one of Formulae 3 to 9 and is contained in an amount of about 0.1 weight percent to about 3 weight,

the organic electrolyte solution further comprises a compound represented by Formula 18a contained in an amount of about 0.1 weight percent to about 2 weight percent, each based on the total weight of the organic electrolyte solution, and

the cyclic carbonate compound represented by Formula 17 is a compound represented by Formula 17a and is contained in an amount of about 1 volume percent to about 10 volume percent, based on a total volume of the organic solvent:

11. The organic electrolyte solution of claim 1 , wherein the lithium salt comprises at least one selected from LiPF 6 , LiBF 4 , LiCF 3 SO 3 , Li(CF 3 SO 2 ) 2 N, LiC 2 F 5 SO 3 , Li(FSO 2 ) 2 N, LiC 4 F 9 SO 3 , LiN(SO 2 CF 2 CF 3 ) 2 , and compounds represented by Formulae 19 to 22:

12. The organic electrolyte solution of claim 1 , wherein a concentration of the lithium salt in the organic electrolyte solution is in a range of about 0.01 molar to about 5 molar, based on a total volume of the organic electrolyte solution.

13. A lithium battery comprising:

a cathode comprising a cathode active material;

an anode comprising an anode active material; and

the organic electrolyte solution of claim 1 disposed between the cathode and the anode.

14. The lithium battery of claim 13 , wherein the cathode active material comprises a lithium transition metal oxide including nickel and at least one transition metal other than nickel, wherein an amount of the nickel is about 60 mole percent or more, based on the total number of moles of the nickel and the at least one transition metal.

15. The lithium battery of claim 14 , wherein the lithium transition metal oxide is represented by Formula 23:

Li a Ni x Co y M z O 2-b A b   Formula 23

wherein, in Formula 23,

1.0≤a≤1.2, 0≤b≤0.2, 0.6≤x≤1, 0<y≤0.3, 0<z≤0.3, and x+y+z=1,

M is at least one of manganese, vanadium, magnesium, gallium, silicon, tungsten, molybdenum, iron, chromium, copper, zinc, titanium, aluminum, and boron, and

A is at least one of F, S, Cl, and Br.

16. The lithium battery of claim 14 , wherein the lithium transition metal oxide is a compound represented by one of Formulae 24 and 25:

LiNi x Co y Mn z O 2   Formula 24

LiNi x Co y Al z O 2   Formula 25

wherein, in Formulae 24 and 25, x, y, and z are each independently 0.6≤x≤0.95, 0<y≤0.2, and 0<z≤0.1.

17. The lithium battery of claim 13 , wherein the anode active material comprises at least one of a silicon compound, a carbonaceous material, and a composite of a silicon compound and a carbonaceous material.

18. The lithium battery of claim 17 , wherein the silicon compound is a silicon oxide of the formula SiO x wherein 0<x<2, and wherein the anode active material comprises a composite of the silicon oxide and the carbonaceous material.

19. The lithium battery of claim 17 , wherein in the composite, the silicon compound is in a form of a silicon nanoparticle, and wherein the carbonaceous material is disposed on the silicon nanoparticle in the form of a coating.

20. The lithium battery of claim 17 , wherein an average secondary particle diameter of the composite of the silicon compound and the carbonaceous material is in a range of about 5 micrometers to about 20 micrometers, and an average particle diameter of the silicon nanoparticles is about 200 nanometers or less.

21. The lithium battery of claim 1 , wherein a direct current internal resistance of the lithium battery after 200 cycles of charging and discharging is about 155% or less than a direct current internal resistance of the lithium battery after 1 cycle of charging and discharging, when determined at 25° C.

22. The lithium battery of claim 1 , wherein an energy density per cell unit volume is about 500 watt hours per liter or greater.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2019
From: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 051366/0480 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 9, 2018
From: PARK, INSUN; KOH, MYONGCHUN; KIM, DONGYOUNG; PARK, EUNHA; KANG, YOONSOK; SEO, JINAH
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 047458/0377 →
Priority Claims (2)
KR 10-2017-0152499 · Nov 15, 2017 · national
KR 10-2018-0131718 · Oct 31, 2018 · national
Continuity (1)
Related Publication 20190148772A1 · May 16, 2019