IP Library Granted Patent US 9,972,866
Granted Patent B2
US 9,972,866 · App. 14/982,855 · Granted May 15, 2018

Electrolyte for lithium secondary battery and lithium secondary battery employing the same

Inventors: Basab Roy (Yongin-si, KR); Dongyoung Kim (Yongin-si, KR); Jinah Seo (Cheongju-si, KR); Hosang Park (Seoul, KR); Yoonsok Kang (Yongin-si, KR); Jungjoo Cho (Hwaseong-si, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
H01M10/0567H01M4/366H01M10/052H01M10/0568H01M10/0569
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Quick Facts
Patent No.
US 9,972,866
App. No.
14/982,855
Granted
May 15, 2018
Kind
B2
Abstract

An electrolyte for a lithium secondary battery, the electrolyte including: an organic ester compound represented by Formula 1; an organic solvent; and a lithium salt: wherein, in Formula 1, R 1 , R 2 , and R 3 are the same or different, and are each independently a group represented by Formula 2: wherein, in Formula 2, R′ is a C1-C10 alkyl group or a C3-C10 cycloalkyl group.

Claims (29)

1. An electrolyte for a lithium secondary battery, the electrolyte comprising:

an organic ester compound;

an organic solvent; and

a lithium salt:

wherein the organic ester compound comprises 3-(butyryloxy)propane-1,2-diyl diacetate, 3-(pentanoyloxy)propane-1,2-diyl diacetate, 3-(isobutyryloxy)propane-1,2-diyl diacetate, 3-((2-methylbutanoyl)oxy) propane-1,2-diyl diacetate, 3-((3-methylbutanoyl)oxy)propane-1,2-diyl diacetate, 3-acetoxypropane-1,2-diyl dipropionate, 3-(butyryloxy)propane-1,2-diyl dipropionate, 3-(isobutyryloxy)propane-1,2-diyl dipropionate, 3-((2-methylbutanoyl)oxy)propane-1,2-diyl dipropionate, 3-((3-methylbutanoyl)oxy)propane-1,2-diyl dipropionate, 3-acetoxy propane-1,2-diyl dibutyrate, 3-(propionyloxy)propane-1,2-diyl dibutyrate, 3-(pentanoyloxy)propane-1,2-diyl dibutyrate, 3-(isobutyryloxy)propane-1,2-diyl dibutyrate, 3-((2-methylbutanoyl)oxy)propane-1,2-diyl dibutyrate, 3-((3-methylbutanoyl)oxy)propane-1,2-diyl dibutyrate, 3-acetoxypropane-1,2-diyl dipentanoate, 3-(butyryloxy)propane-1,2-diyl dipentanoate, 3-(propionyloxy)propane-1,2-diyl dipentanoate, 3-(isobutyryloxy)propane-1,2-diyl dipentanoate, 3-((2-methylbutanoyl)oxy)propane-1,2-diyl dipentanoate, 3-((3-methylbutanoyl)oxy)propane-1,2-diyl dipentanoate, 2-(pentanoyloxy)propane-1,3-diyl diacetate, 2-(propionyloxy)propane-1,3-diyl diacetate, 2-(butyryloxy)propane-1,3-diyl diacetate, 2-(isobutyryloxy)propane-1,3-diyl diacetate, 2-((3-methylbutanoyl)oxy)propane-1,3-diyl diacetate, 2-((2-methylbutanoyl)oxy)propane-1,3-diyl diacetate, 2-acetoxypropane-1,3-diyl dipropionate, 2-(pentanoyloxy)propane-1,3-diyl dipropionate, 2-(butyryloxy)propane-1,3-diyl dipropionate, 2-(isobutyryloxy)propane-1,3-diyl dipropionate, 2-((3-methylbutanoyl)oxy)propane-1,3-diyl dipropionate, 2-((2-methylbutanoyl)oxy)propane-1,3-diyl dipropionate, 2-acetoxypropane-1,3-diyl dibutyrate, 2-(propionyloxy)propane-1,3-diyl dibutyrate, 2-(butyryloxy)propane-1,3-diyl dibutyrate, 2-(isobutyryloxy)propane-1,3-diyl dibutyrate, 2-((3-methylbutanoyl)oxy)propane-1,3-diyl dibutyrate, 2-((2-methylbutanoyl)oxy)propane-1,3-diyl dibutyrate, 2-acetoxypropane-1,3-diyl dipentanoate, 2-(propionyloxy)propane-1,3-diyl dipentanoate, 2-(butyryloxy)propane-1,3-diyl dipentanoate, 2-(isobutyryloxy)propane-1,3-diyl dipentanoate, 2-((3-methylbutanoyl)oxy)propane-1,3-diyl dipentanoate, 2-((2-methylbutanoyl)oxy)propane-1,3-diyl dipentanoate, or a combination thereof, and

wherein the amount of the organic ester compound is from about 10 percent by weight to about 70 percent by weight based on a total weight of the electrolyte.

2. The electrolyte of claim 1 , wherein the organic ester compound has a boiling point of about 150° C. or greater.

3. The electrolyte of claim 1 , wherein the amount of the organic ester compound is from about 12 percent by weight to about 45 percent by weight based on the total weight of the electrolyte.

4. The electrolyte of claim 1 , wherein an anion of the lithium salt comprises F − , Cl − , Br − , I − , NO 3 − , N(CN) 2 − , BF 4 − , ClO 4 − , PF 6 − , (CF 3 ) 2 PF 4 − , (CF 3 ) 3 PF 3 − , (CF 3 ) 4 PF 2 − , (CF 3 ) 5 PF − , (CF 3 ) 6 P − , CF 3 SO 3 − , CF 3 CF 2 SO 3 − , (CF 3 SO 2 ) 2 N − , (FSO 2 ) 2 N − , CF 3 CF 2 (CF 3 ) 2 CO − , (CF 3 SO 2 ) 2 CH − , (SF 5 ) 3 C − , (CF 3 SO 2 ) 3 C − , CF 3 (CF 2 ) 7 SO 3 − , CF 3 CO 2 − , CH 3 CO 2 − , SCN − , (CF 3 CF 2 SO 2 ) 2 N − , or a combination thereof.

5. The electrolyte of claim 1 , wherein the organic solvent comprises an ether solvent, an ester solvent, an amide solvent, a linear carbonate solvent, a cyclic carbonate solvent, or a combination thereof.

6. The electrolyte of claim 5 , wherein the ether solvent comprises dimethyl ether, diethyl ether, dipropyl ether, methylethyl ether, methyl propyl ether, ethyl propyl ether, or a combination thereof.

7. The electrolyte of claim 5 , wherein the ester solvent comprises methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate, propyl propionate, γ-butyrolactone, γ-valerolactone, γ-caprolactone, σ-valerolactone, ε-caprolactone, or a combination thereof.

8. The electrolyte of claim 5 , wherein the amide solvent comprises N,N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, or a combination thereof.

9. The electrolyte of claim 5 , wherein the linear carbonate solvent comprises dimethyl carbonate, diethyl carbonate, dipropyl carbonate, ethyl methyl carbonate (EMC), methyl propyl carbonate, ethyl propyl carbonate, a halide thereof, or a combination thereof.

10. The electrolyte of claim 5 , wherein the cyclic carbonate solvent comprises ethylene carbonate, propylene carbonate, 1,2-butylene carbonate, 2,3-butylene carbonate, 1,2-pentylene carbonate, 2,3-pentylene carbonate, vinylene carbonate, a halide thereof, or a combination thereof.

11. The electrolyte of claim 1 , wherein the electrolyte further comprises an additive to form a solid electrolyte interface membrane, the additive comprising vinylene carbonate, vinyl ethylene carbonate, fluoroethylene carbonate, a cyclic sulfite, a saturated sultone, an unsaturated sultone, an acyclic sulfone, or a combination thereof.

12. The electrolyte of claim 11 ,

wherein the cyclic sulfite is ethylene sulfite, methyl ethylene sulfite, ethyl ethylene sulfite, 4,5-dimethyl ethylene sulfite, 4,5-diethyl ethylene sulfite, propylene sulfite, 4,5-dimethyl propylene sulfite, 4,5-diethyl propylene sulfite, 4,6-dimethyl propylene sulfite, 4,6-diethyl propylene sulfite, 1,3-butylene glycol sulfite, or a combination thereof, and

wherein the acyclic sulfone is divinyl sulfone, dimethyl sulfone, diethyl sulfone, methylethyl sulfone, methylvinyl sulfone, or a combination thereof.

13. The electrolyte of claim 11 ,

wherein the saturated sultone is 1,3-propane sultone, 1,4-butane sultone, or a combination thereof, and

wherein the unsaturated sultone is ethene sultone, 1,3-propene sultone, 1,4-butene sultone, 1-methyl-1,3-propene sultone, or a combination thereof.

14. The electrolyte of claim 11 , wherein an amount of the additive to form a solid electrolyte interface membrane is from about 0.01 parts by weight to about 10 parts by weight based on a total weight of the electrolyte for a lithium secondary battery.

15. The electrolyte of claim 1 , wherein a concentration of the lithium salt may be from about 0.6 moles per liter to about 2.0 moles per liter.

16. A lithium secondary battery comprising:

a cathode;

an anode; and

the electrolyte according to claim 1 , disposed between the cathode and the anode.

17. The lithium secondary battery of claim 16 , further comprising a film disposed on a surface of the anode, wherein the film comprises the organic ester compound.

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 Apr 15, 2016
From: ROY, BASAB; KIM, DONGYOUNG; SEO, JINAH; PARK, HOSANG; KANG, YOONSOK; CHO, JUNGJOO
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 038443/0305 →
Priority Claims (1)
KR 10-2014-0195962 · Dec 31, 2014 · national
Continuity (1)
Related Publication 20160190649A1 · Jun 30, 2016