# US 12,770,921 B2 · Additives for nonaqueous electrolyte and lithium secondary battery containing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,770,921 B2 - Document ID: US12770921B2 - Status: Granted - Kind: B2 - Application number: 17/983,896 - Filed: 2022-11-09 - Published: 2023-05-18 - Granted: 2026-10-20 - Earliest claimed: 2021-11-16 - Assignees: LG Energy Solution, Ltd. - Applicants: LG Energy Solution, Ltd. - Inventors: You Kyeong Jeong; Kyoung Ho Ahn; Junhyeok Han; Won-Kyung Shin; Wontae Lee; Su Hyeon Ji; Youngho Oh - Web page: https://patentgrep.com/patent/US12770921B2 ## CPC - H01M 10/0567: characterised by the additives - H01M 4/386: {Silicon or alloys based on silicon} - H01M 4/485: of mixed oxides or hydroxides for inserting or intercalating light metals, e.g. LiTi2O4 or LiTi2OxFy (H01M4/505, H01M4/525 take precedence) - H01M 4/505: of mixed oxides or hydroxides containing manganese for inserting or intercalating light metals, e.g. LiMn2O4 or LiMn2OxFy - H01M 4/525: of mixed oxides or hydroxides containing iron, cobalt or nickel for inserting or intercalating light metals, e.g. LiNiO2, LiCoO2 or LiCoOxFy - H01M 4/583: Carbonaceous material, e.g. graphite-intercalation compounds or CFx - H01M 10/0568: characterised by the solutes - H01M 10/0569: characterised by the solvents - H01M 50/46: Separators, membranes or diaphragms characterised by their combination with electrodes - H01M 2004/027: {Negative electrodes} - H01M 2004/028: {Positive electrodes} - H01M 2300/0028: characterised by the solvent - H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY ## Abstract An additive for a non-aqueous electrolyte, a non-aqueous electrolyte including the same, and a lithium secondary battery including the same are disclosed herein. The additive includes an ionic compound to form a coating film on an electrode surface, thereby preventing gas generation at high temperature, a cell open-circuit voltage (OCV) drop, and a decrease in capacity retention rate, which are caused by elution of metal ions from an electrode. The additive improves durability, performance, and high temperature safety of the battery. ## Claims ### Claim 1 An electrolyte additive for a secondary battery, comprising: a compound represented by Formula 1: wherein, R1 is hydrogen or an alkyl group having 1 to 4 carbon atoms, R2 includes one or more selected from an alkylene group having 1 to 10 carbon atoms, an oxyalkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 5 to 10 carbon atoms, or each of which is are optionally substituted with a fluorine atom, R3 is a fluoro group, an alkyl group having 1 to 10 carbon atoms optionally substituted with a fluorine atom, an alkoxy group having 1 to 10 carbon atoms optionally substituted with a fluorine atom, or optionally substituted with a fluorine atom, provided when R2 is an alkylene group having 1 to 10 carbon atoms, R3 is not an alkyl group having 1 to 10 carbon atoms substituted with a fluorine atom, X is an oxygen atom (O) or —NR4, R4 is hydrogen or an alkyl group having 1 to 4 carbon atoms, M includes one or more of lithium, sodium, potassium, tetraalkyl ammonium having 1 to 4 carbon atoms, or tetraalkyl phosphonium having 1 to 4 carbon atoms, l is an integer of 1 to 6, and each of m and n is an integer of 2 to 20. ### Claim 2 (depends on 1) The electrolyte additive of claim 1, wherein R1 is hydrogen or a methyl group, R2 comprises one or more selected from a methylene group, an ethylene group, a propylene group, an oxymethylene group, an oxyethylene group, an oxypropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, R3 is a fluoro group, a methyl group, an ethyl group, a propyl group, a methoxy group, an ethoxy group, X is an oxygen atom (O), —NH, or —NCH3, M is lithium, l is an integer of 1 or 2, and each of m and n is an integer of 2 to 10. ### Claim 3 (depends on 1) The electrolyte additive of claim 1, wherein the compound is represented by any one of Structural Formulas below: ### Claim 4 An electrolyte composition for a lithium secondary battery, comprising: a non-aqueous organic solvent; a lithium salt; and a compound represented by Formula 1: wherein, R1 is hydrogen or an alkyl group having 1 to 4 carbon atoms, R2 includes one or more selected from an alkylene group having 1 to 10 carbon atoms, an oxyalkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 5 to 10 carbon atoms, or each of which is are optionally substituted with a fluorine atom, R3 is a fluoro group, an alkyl group having 1 to 10 carbon atoms optionally substituted with a fluorine atom, an alkoxy group having 1 to 10 carbon atoms optionally substituted with a fluorine atom, or optionally substituted with a fluorine atom, provided when R2 is an alkylene group having 1 to 10 carbon atoms, R3 is not an alkyl group having 1 to 10 carbon atoms substituted with a fluorine atom, X is an oxygen atom (O) or —NR4, R4 is hydrogen or an alkyl group having 1 to 4 carbon atoms, M comprises one or more selected from the group consisting of one or more selected from the group consisting of lithium, sodium, potassium, tetraalkyl ammonium having 1 to 4 carbon atoms, and tetraalkyl phosphonium having 1 to 4 carbon atoms, l is an integer of 1 to 6, and each of m and n is an integer of 2 to 20. ### Claim 5 (depends on 4) The electrolyte composition of claim 4, wherein the compound represented by Formula 1 is present in an amount of 0.01 to 3 wt % with respect to the total weight of the electrolyte composition. ### Claim 6 (depends on 4) The electrolyte composition of claim 4, wherein the lithium salt comprises one or more of LiCl, LiBr, LiI, LiClO4, LiBF4, LiB10Cl10, LiPF6, LiCF3SO3, LiCF3CO2, LiAsF6, LiSbF6, LiAlCl4, CH3SO3Li, (CF3SO2)2Nli, or (FSO2)2NLi. ### Claim 7 (depends on 4) The electrolyte composition of claim 4, wherein the non-aqueous organic solvent comprises one or more of N-methyl-2-pyrrolidinone, ethylene carbonate, propylene carbonate, butylene carbonate, dimethyl carbonate, diethyl carbonate, γ-butyrolactone, 1,2-dimethyoxy ethane, tetrahydroxy franc, 2-methyl tetrahydrofuran, dimethyl sulfoxide, 1,3-dioxolane, formamide, dimethylformamide, dioxolane, acetonitrile, nitromethane, methyl formate, methyl citrate, phosphoric acid triester, trimethoxy methane, a dioxolane derivative, sulfolane, methyl sulfolane, 1,3-dimethyl-2-imidazolidinone, a propylene carbonate derivative, a tetrahydrofuran derivative, ether, methyl propionate, or ethyl propionate. ### Claim 8 (depends on 4) A lithium secondary battery, comprising: an electrode assembly having a positive electrode, a negative electrode, and a separator interposed between the positive electrode and the negative electrode, and the electrolyte of claim 4, wherein the positive electrode comprises one or more positive electrode active materials of lithium metal oxides represented by Formulas 2 or 3: Lix[NiyCO2MnwM1v]O2 [Formula 2] LiM2pMn(2−p)O4 [Formula 3] In Formulas 2 and 3, M1 is one or more elements selected from the group consisting of W, Cu, Fe, V, Cr, Ti, Zr, Zn, Al, In, Ta, Y, La, Sr, Ga, Sc, Gd, Sm, Ca, Ce, Nb, Mg, B, and Mo, x, y, z, w and v satisfy 1.0≤x≤1.30, 0.5≤y<1, 0