# US 10,320,032 B2 · Organic electrolytic solution and lithium battery using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,320,032 B2 - Document ID: US10320032B2 - Status: Granted - Kind: B2 - Application number: 15/459,672 - Filed: 2017-03-15 - Published: 2017-09-21 - Granted: 2019-06-11 - Earliest claimed: 2016-03-18 - Assignees: Samsung SDI Co., Ltd. - Applicants: Samsung SDI Co., Ltd. - Inventors: AeRan Kim; MiYoung Son; HyunBong Choi; MyungHeui Woo; SeungTae Lee; HaRim Lee; AeHui Goh; WooCheol Shin - Web page: https://patentgrep.com/patent/US10320032B2 ## CPC - H01M 10/0567: characterised by the additives - C07D 327/04: Five-membered rings - C07D 333/48: by oxygen atoms - H01M 10/052: Li-accumulators - H01M 10/0568: characterised by the solutes - H01M 2300/0025: Organic electrolyte - 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 - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract Provided is an organic electrolyte solution that includes a lithium salt, an organic solvent, and a sulfonate ester-based compound represented by Formula 1: R2—O—S(═O)2—R1 wherein, in Formula 1, R1 may be a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and R2 may be a substituted or unsubstituted cyclic sulfone group. ## Claims ### Claim 1 An organic electrolyte solution, comprising: a lithium salt; an organic solvent; and a sulfonate ester-based compound represented by Formula 1, R2—O—S(═O)2—R1 wherein, in Formula 1, R1 is a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and R2 is represented by Formula 2: wherein, in Formula 2, R3 and R4 are each independently hydrogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, or a polar functional group having at least one heteroatom, n is an integer selected from 4 to 9, and * represents the R2-oxygen bond in Formula 2, provided that at least one of R3 and R4 is a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, or a polar functional group having at least one heteroatom. ### Claim 2 (depends on 1) The organic electrolyte solution as claimed in claim 1, wherein: at least one of R3 and R4 is the polar functional group having at least one heteroatom, and the polar functional group having at least one heteroatom includes at least one selected from —F, —Cl, —Br, —I, —C(═O)OR16, —OC(═O)OR16, —R15OC(═O)OR16, —C(═O)R16, —R15C(═O)R16, —OC(═O)R16, —R15OC(═O)R16, —C(═O)—O—C(═O)R16, —R15C(═O)—O—C(═O)R16, —SR16, —R15SR16, —SSR16, —R15SSR16, —S(═O)R16, —R15S(═O)R16, —R15C(═S)R16, —R15C(═S)SR16, —R15SO3R16, —SO3R16, —NNC(═S)R16, —R15NNC(═S)R16, —R15N═C═S, —NCO, —R15—NCO, —NO2, —R15NO2, —R15SO2R6, —SO2R16, wherein R11 and R15 are each independently a C1-C20 alkylene group that is unsubstituted or substituted with halogen, a C2-C20 alkenylene group that is unsubstituted or substituted with halogen, a C2-C20 alkynylene group that is unsubstituted or substituted with halogen, a C3-C12 cycloalkylene group that is unsubstituted or substituted with halogen, a C6-C40 arylene group that is unsubstituted or substituted with halogen, a C2-C40 heteroarylene group that is unsubstituted or substituted with halogen, a C7-C15 alkylarylene group that is unsubstituted or substituted with halogen, or a C7-C15 aralkylene group that is unsubstituted or substituted with halogen, and R12, R13, R14, and R16 are each independently hydrogen, a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C3-C12 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, a C7-C15 alkylaryl group that is unsubstituted or substituted with halogen, a C7-C15 trialkylsilyl group that is unsubstituted or substituted with halogen, or a C7-C15 aralkyl group that is unsubstituted or substituted with halogen. ### Claim 3 (depends on 1) The organic electrolyte solution as claimed in claim 1, wherein R2 is a substituted or unsubstituted sulfolanyl group. ### Claim 4 (depends on 3) The organic electrolyte solution as claimed in claim 3, wherein: the sulfolanyl group is substituted, and the substituent of the sulfolanyl group is a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, or a polar functional group having at least one heteroatom. ### Claim 5 (depends on 1) The organic electrolyte solution as claimed in claim 1, wherein the sulfonate ester-based compound of Formula 1 is represented by Formula 3 or Formula 4, wherein, in Formula 3 and Formula 4, Ra and Ri are each independently a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and Rb, Rc, Rd, Re, Rf, Rg, and Rh are each independently hydrogen, a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C2-C20 alkenyl group that is unsubstituted or substituted with halogen, a C2-C20 alkynyl group that is unsubstituted or substituted with halogen, a C1-C20 alkoxy group that is unsubstituted or substituted with halogen, a C5-C20 cycloalkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen. ### Claim 6 (depends on 5) The organic electrolyte solution as claimed in claim 5, wherein Ra and Ri are each independently F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group, and Rb, Rc, Rd, Re, Rf, Rg, and Rh are each independently hydrogen, F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group. ### Claim 7 (depends on 1) The organic electrolyte solution as claimed in claim 1, wherein the sulfonate ester-based compound of Formula 1 is represented by Formula 5 or Formula 6, wherein, in Formula 5 and Formula 6, Rj and Rm, are each independently a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen, and Rk and Rl are each independently hydrogen, a halogen, a C1-C20 alkyl group that is unsubstituted or substituted with halogen, a C6-C40 aryl group that is unsubstituted or substituted with halogen, or a C2-C40 heteroaryl group that is unsubstituted or substituted with halogen. ### Claim 8 (depends on 7) The organic electrolyte solution as claimed in claim 7, wherein Rj and Rm are each independently F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group, and Rk and Rl are each independently hydrogen, F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a trifluoromethyl group, a tetrafluoroethyl group, a phenyl group, a naphthyl group, a tetrafluorophenyl group, a pyrrolyl group, or a pyridinyl group. ### Claim 9 (depends on 1) The organic electrolyte solution as claimed in claim 1, wherein an amount of the sulfonate ester-based compound is in a range of about 0.01 wt % to about 10 wt % based on the total weight of the organic electrolyte solution. ### Claim 10 (depends on 1) The organic electrolyte solution as claimed in claim 1, wherein the lithium salt in the organic electrolyte solution includes at least one selected from LiPF6, LiBF4, LiSbF6, LiAsF6, LiClO4, LiCF3SO3, Li(CF3SO2)2N, LiC4F9SO3, LiAlO2, LiAlCl4, LiN(CxF2x+1SO2)(CyF2y+1SO2) (where 2≤x≤20 and 2≤y≤20), LiCl, and LiI. ### Claim 11 An organic electrolyte solution, comprising: a lithium salt; an organic solvent; and a sulfonate ester-based compound represented by one of the following Formulae 8 to 14, 16 18 to 22: ### Claim 12 (depends on 1) A lithium battery, comprising: a cathode, an anode, and the organic electrolyte solution as claimed in claim 1. ### Claim 13 (depends on 12) The lithium battery as claimed in claim 12, wherein the cathode includes a lithium transition metal oxide having a nickel-containing layered structure. ### Claim 14 (depends on 12) The lithium battery as claimed in claim 12, wherein the lithium battery has a voltage of about 3.8 V or higher. ### Claim 15 (depends on 11) A lithium battery, comprising: a cathode, an anode, and the organic electrolyte solution as claimed in claim 11.