IP Library Granted Patent US 11,038,202
Granted Patent B2
US 11,038,202 · App. 16/049,963 · Granted Jun 15, 2021

Bis(phenyl) methanedisulfonate-based additive and lithium secondary battery comprising the same

Inventors: Myongchun Koh (Hwaseong-si, KR); Yoonsok Kang (Seongnam-si, KR); Eunha Park (Seoul, KR); Jinah Seo (Seoul, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
H01M10/0567H01M4/505H01M4/525H01M10/0525H01M4/364H01M4/386H01M4/587H01M2004/028H01M2300/004H01M2300/0025
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Quick Facts
Patent No.
US 11,038,202
App. No.
16/049,963
Granted
Jun 15, 2021
Kind
B2
Abstract

An electrolyte includes: a lithium salt; a non-aqueous solvent; and a disulfonate compound represented by Formula 1: wherein, in Formula 1, R 1 and R 2 are each independently a fluorine, a cyano group, a nitro group, or a methyl group substituted with at least one fluorine, R 11 to R 14 are each independently a hydrogen, a deuterium, a fluorine, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, or a substituted or unsubstituted C 2 -C 10 alkynyl group, a1 and a2 are each independently an integer of 1 to 5, a11 and a12 are each independently an integer of 0 to 4, and a sum of a1 and a11 is 5, and a sum of a2 and a12 is 5.

Claims (47)

1. A lithium secondary battery comprising:

a positive electrode,

a negative electrode, and

an electrolyte disposed between the positive electrode and the negative electrode,

wherein the electrolyte comprises:

a lithium salt;

a non-aqueous solvent; and

about 0.1 weight percent or greater to less than about 3 weight percent of a disulfonate compound represented by Formula 1, each of which is based on a total weight of the electrolyte,

and the positive electrode comprises a positive active material represented by Formula 2:

wherein, in Formula 1,

R 1 and R 2 are each independently a cyano group or a nitro group,

R 11 to R 14 are each independently a hydrogen, a deuterium, a fluorine, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, or a substituted or unsubstituted C 2 -C 10 alkynyl group,

a1 and a2 are each independently an integer of 1 to 5,

a11 and a12 are each independently an integer of 0 to 4, and

a sum of a1 and a11 is 5, and a sum of a2 and a12 is 5;

Formula 2

Li x Ni y M 1−y O 2−z A z

wherein, in Formula 2, 0.9≤x≤1.2, 0.1≤y≤0.98, 0≤z<0.2,

M includes Al, Mg, Mn, Co, Fe, Cr, V, Ti, Cu, B, Ca, Zn, Zr, Nb, Mo, Sr, Sb, W, Bi, or a combination thereof; and

A is an element having an oxidation number of −1, −2 or −3.

2. The lithium secondary battery of claim 1 , wherein the disulfonate compound represented by Formula 1 is present in an amount of about 1 weight percent to about 2 weight percent.

3. The lithium secondary battery of claim 1 ,

wherein R 1 and R 2 are each independently a cyano group.

4. The lithium secondary battery of claim 1 , wherein R 11 to R 14 are each independently a hydrogen, a substituted or unsubstituted C 1 -C 10 alkyl group, or a substituted or unsubstituted C 2 -C 10 alkenyl group.

5. The lithium secondary battery of claim 1 , wherein a1 and a2 are each independently 1, 2, or 5.

6. The lithium secondary battery of claim 1 , wherein the lithium salt comprises lithium difluoro(oxalato)borate, lithium bis(oxalato)borate, lithium difluoro bis(oxalato)phosphate, LiBF 4 , LiPF 6 , LiCF 3 SO 3 , (CF 3 SO 2 ) 2 NLi, (FSO 2 ) 2 NLi, or a combination thereof.

7. The lithium secondary battery of claim 1 , wherein the non-aqueous solvent comprises dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, dipropyl carbonate, methylpropyl carbonate, ethylpropyl carbonate, ethylene carbonate, propylene carbonate, butylene carbonate, or a combination thereof.

8. The lithium secondary battery of claim 1 , wherein the non-aqueous solvent further includes fluoroethylene carbonate.

9. The lithium secondary battery of claim 1 , wherein the positive active material is represented by Formula 3 or Formula 4:

Formula 3

LiNi y′ CO 1−y′−z′ Mn z′ O 2

Formula 4

LiNi y′ Co 1−y′−z′ Mn z′ O 2

wherein, in Formula 3 and 4, 0.9≤x′≤1.2, 0.8≤y′≤0.98, 0<z′<0.1, and 0<1−y′−z′<0.2.

10. The lithium secondary battery of claim 1 , wherein the positive electrode comprises LiNi 0.80 Co 0.15 Mn 0.05 O 2 , LiNi 0.85 Co 0.1 Mn 0.05 O 2 , LiNi 0.88 Co 0.08 Mn 0.04 O 2 , LiNi 0.88 Co 0.08 Al 0.04 O 2 , Li 1.02 Ni 0.80 Co 0.15 Mn 0.05 O 2 , Li 1.02 Ni 0085 Co 0.10 Mn 0005 O 2 , Li 1.02 Ni 0.88 Co 00.8 Mn 00.4 O 2 , or a combination thereof.

11. The lithium secondary battery of claim 1 , wherein the lithium secondary battery has a capacity retention of about 80% or greater and a direct current internal resistance increase rate of less than about 150% after 300 charge/discharge cycles at a temperature of about 45° C.

12. The lithium secondary battery of claim 1 , wherein the lithium secondary battery has a cell energy density of about 500 watt hours per liter or greater.

13. The lithium secondary battery of claim 1 , further comprising a carbonate including a carbon-carbon single bond, a carbonate including a carbon-carbon double bond, a carbonate including a carbon-carbon triple bond, a carboxylic anhydride including a carbon-carbon double bond, a carboxylic anhydride including a carbon-carbon triple bond, or a combination thereof.

14. The lithium secondary battery of claim 1 , further comprising a vinylene carbonate, a vinyl ethylene carbonate, a maleic anhydride, a succinic anhydride, or a combination thereof.

15. The lithium secondary battery of claim 1 , further comprising a phosphorus-containing compound, a sulfur-containing compound other than the disulfonate compound represented by Formula 1, or a combination thereof, wherein the phosphorus-containing compound, the sulfur-containing compound other than the disulfonate compound represented by Formula 1, or the combination thereof is present in an amount of about 0.1 weight percent to about 2 weight percent, based on a total weight of the electrolyte.

16. The lithium secondary battery of claim 15 , wherein the phosphorus-containing compound comprises a phosphine compound, a phosphite compound, or a combination thereof.

17. The lithium secondary battery of claim 1 , wherein the negative electrode comprises a negative active material comprising a metal or a metalloid alloyable with lithium, a carbonaceous negative active material, or a combination thereof.

18. The lithium secondary battery of claim 17 , wherein the negative active material comprising a metalloid alloyable with lithium comprises silicon, a silicon-carbon composite material, SiO a′ , wherein 0<a′<2, or a combination thereof.

19. The lithium secondary battery of claim 1 ,

wherein the negative electrode comprises a negative active material comprising a silicon-carbon composite that includes silicon particles, and

wherein the silicon particles have an average particle diameter of about 200 nanometers or less.

20. The lithium secondary battery of claim 19 , wherein the silicon-carbon composite includes graphite to provide the negative electrode with a capacity of 600 milliampere hours per gram (mAh/g) to about 2000 mAh/g.

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 Jul 31, 2018
From: KOH, MYONGCHUN; KANG, YOONSOK; PARK, EUNHA; SEO, JINAH
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 046508/0873 →
Priority Claims (1)
KR 10-2017-0103722 · Aug 16, 2017 · national
Continuity (1)
Related Publication 20190058218A1 · Feb 21, 2019
Cited By (1)
US 12,266,788