# US 10,122,046 B2 · Electrolyte compositions for high voltage lithium-ion batteries > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,122,046 B2 - Document ID: US10122046B2 - Status: Granted - Kind: B2 - Application number: 14/506,316 - Filed: 2014-10-03 - Published: 2016-04-07 - Granted: 2018-11-06 - Earliest claimed: 2014-10-03 - Assignees: Uchicago Argonne, LLC - Applicants: Uchicago Argonne, LLC - Inventors: Daniel Abraham; Ye Zhu - Web page: https://patentgrep.com/patent/US10122046B2 ## CPC - H01M 10/0567: characterised by the additives - H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries - H01M 10/0568: characterised by the solutes - H01M 10/0569: characterised by the solvents - H01M 2300/0037: Mixture of solvents - Y02E 60/10: Energy storage using batteries - H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract The present invention provides an electrolyte composition for a lithium-ion battery comprising LiPF6 in a liquid carrier comprising a carbonate ester and an unsaturated organoboron compound comprising two or three unsaturated hydrocarbon groups, each unsaturated hydrocarbon group being covalently bonded to a boron atom. The unsaturated hydrocarbon groups are independently selected from vinyl, allyl, propargyl, substituted vinyl, substituted allyl, and substituted propargyl. The substituents of the substituted vinyl, allyl and propargyl groups independently comprise one or more of alkyl and phenyl. The alkyl and phenyl groups optionally can bear one or more substituent selected from halogen (e.g., F), hydroxy, amino, alkoxy, and perfluoroalkoxy. ## Claims ### Claim 1 An electrochemical cell comprising an anode, a cathode, and a lithium-containing electrolyte contacting the anode and the cathode; the electrolyte comprising about 1 to 1.5 M LiPF6 in a liquid carrier comprising a carbonate ester containing about 0.25 to about 2 percent by weight of an unsaturated organoboron compound, based on the total weight of the liquid carrier; wherein the organoboron compound comprises two or three unsaturated hydrocarbon groups, each unsaturated hydrocarbon group being covalently bonded by a carbon atom thereof to a boron atom of the organoboron compound; wherein the unsaturated hydrocarbon groups are independently selected from vinyl, allyl, propargyl, substituted vinyl, substituted allyl, and substituted propargyl; the substituents of the substituted vinyl, allyl and propargyl groups independently comprise one or more of alkyl and phenyl; and the alkyl and phenyl groups optionally comprise one or more substituent selected from halogen, hydroxy, amino, alkoxy, and perfluoroalkoxy; and wherein the organoboron compound has the formula Z-X3, wherein Z is B, and each X independently is selected from vinyl, allyl, propargyl, substituted vinyl, substituted allyl, and substituted propargyl; the substituents of the substituted vinyl, allyl and propargyl groups independently comprise one or more of alkyl and phenyl; and the alkyl and phenyl groups optionally comprise one or more substituent selected from halogen, hydroxy, amino, alkoxy, and perfluoroalkoxy; and wherein the anode comprises graphite and the cathode comprises a lithium metal oxide material providing a cell voltage of about 4.5 V to 5V. ### Claim 2 (depends on 1) The electrochemical cell of claim 1, wherein the carbonate ester comprises at least one compound selected from ethylene carbonate, propylene carbonate, dimethyl carbonate, and ethyl methyl carbonate. ### Claim 3 (depends on 1) The electrochemical cell of claim 1, wherein each X is vinyl. ### Claim 4 (depends on 1) The electrochemical cell of claim 1, wherein each X is allyl or each X is propargyl. ### Claim 5 (depends on 1) The electrochemical cell of claim 1, wherein the liquid carrier comprises ethylene carbonate, ethyl methyl carbonate, and each X is vinyl, allyl or propargyl. ### Claim 6 An electrochemical cell comprising an anode, a cathode, and an electrolyte contacting the anode and the cathode; the electrolyte comprising about 1 M to 1.5 M of a lithium salt consisting of LiPF6 in a liquid carrier comprising a carbonate ester containing about 0.25 to about 2 percent by weight of an organoboron compound of formula Z-X3, based on the total weight of the liquid carrier, wherein Z is a boroxine ring; each X independently is selected from vinyl, allyl, propargyl, substituted vinyl, substituted allyl, and substituted propargyl; the substituents of the substituted vinyl, allyl and propargyl groups independently comprise one or more of alkyl and phenyl; and the alkyl and phenyl groups optionally comprise one or more substituent selected from halogen, hydroxy, amino, alkoxy, and perfluoroalkoxy; and wherein the anode comprises graphite and the cathode comprises a lithium metal oxide material providing a cell voltage of about 4.5 V to 5 V. ### Claim 7 (depends on 6) The electrochemical cell of claim 6, wherein the carbonate ester comprises at least one compound selected from ethylene carbonate, propylene carbonate, dimethyl carbonate, and ethyl methyl carbonate. ### Claim 8 (depends on 6) The electrochemical cell of claim 6, wherein each X is vinyl. ### Claim 9 (depends on 6) The electrochemical cell of claim 6, wherein the carbonate ester comprises a mixture of less than 50 percent by weight ethylene carbonate and greater than 50 percent by weight ethyl methyl carbonate. ### Claim 10 An electrochemical cell comprising an anode, a cathode, and an electrolyte contacting the anode and the cathode; the electrolyte comprising about 1 M to about 1.5 M of a lithium salt consisting of LiPF6 in a liquid carrier comprising a carbonate ester and about 0.25 percent by weight of trivinylboroxine, based on the total weight of the liquid carrier, wherein the anode comprises graphite, and the cathode comprises a lithium nickel/manganese/cobalt oxide material providing a cell voltage of about 4.5 V to 5 V. ### Claim 11 (depends on 10) The electrochemical cell of claim 10, wherein the carbonate ester comprises at least one compound selected from ethylene carbonate, propylene carbonate, dimethyl carbonate, and ethyl methyl carbonate. ### Claim 12 (depends on 10) The electrochemical cell of claim 10, wherein the carbonate ester comprises ethylene carbonate and ethyl methyl carbonate in a respective weight ratio of about 3:7. ### Claim 13 (depends on 10) The electrochemical cell of claim 10, wherein the LiPF6 is present in the electrolyte at a concentration of about 1.2 M. ### Claim 14 (depends on 10) The electrochemical cell of claim 10, wherein the cathode comprises a lithium metal oxide material of formula Li 1+xM1−xO2, wherein x is in the range of 0 to 0.5, and wherein M comprises a combination of Ni, Co, and Mn. ### Claim 15 (depends on 10) The electrochemical cell of claim 10, wherein the cathode comprises a lithium metal oxide material of formula Li1.2Ni0.15Mn0.55Co0.1O2. ### Claim 16 (depends on 6) The electrochemical cell of claim 6, wherein the cathode comprises a lithium metal oxide material of formula Li 1+xM1−xO2, wherein x is in the range of 0 to 0.5, and wherein M comprises a combination of Ni, Co, and Mn. ### Claim 17 (depends on 6) The electrochemical cell of claim 6, wherein the cathode comprises a lithium metal oxide material of formula Li1.2Ni0.15Mn0.55Co0.1O2. ### Claim 18 (depends on 1) A battery comprising a plurality of the electrochemical cells of claim 1 connected in series, in parallel, or both in series and in parallel. ### Claim 19 (depends on 6) A battery comprising a plurality of the electrochemical cells of claim 6 connected in series, in parallel, or both in series and in parallel. ### Claim 20 (depends on 10) A battery comprising a plurality of the electrochemical cells of claim 10 connected in series, in parallel, or both in series and in parallel.