# US 10,312,546 B2 · Non-aqueous liquid electrolyte for secondary battery and secondary battery > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,312,546 B2 - Document ID: US10312546B2 - Status: Granted - Kind: B2 - Application number: 14/601,321 - Filed: 2015-01-21 - Published: 2015-05-14 - Granted: 2019-06-04 - Earliest claimed: 2012-07-27 - Assignees: FUJIFILM Corporation - Applicants: Fujifilm Corporation - Inventors: Kunihiko Kodama - Web page: https://patentgrep.com/patent/US10312546B2 ## CPC - H01M 10/0567: characterised by the additives - H01M 4/131: Electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx - H01M 4/133: Electrodes based on carbonaceous material, e.g. graphite-intercalation compounds or CFx - 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 4/587: for inserting or intercalating light metals - H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries - H01M 2004/027: {Negative electrodes} - H01M 2004/028: {Positive electrodes} - H01M 2300/0025: Organic electrolyte - 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 A non-aqueous liquid electrolyte for a secondary battery, containing an electrolyte and a compound (A) represented by any one of formulae (I-1) to (I-3) in an organic solvent: wherein X1 represents an alkyl group substituted with a halogen atom; Y1 represents a hydrogen atom or an organic group; and ma represents an integer from 1 to 6; wherein X2 represents a group having an oxygen atom; Y2 represents a hydrogen atom or an organic group; and mb represents an integer from 1 to 6; and wherein Y3 represents an organic group having 4 or more carbon atoms, or an organic group having an oxygen atom or a nitrogen atom; and mc represents an integer from 1 to 6. ## Claims ### Claim 1 A non-aqueous liquid electrolyte for a secondary battery, containing an electrolyte and a compound (A) represented by any one of formulae (I-1) to (I-3) in an organic solvent: wherein, in formula (I-1), X1 represents an alkyl group substituted with a halogen atom; Y1 represents a hydrogen atom or an organic group; and ma represents an integer from 1 to 6; wherein, in formula (I-2), X2 represents a group having an oxygen atom; Y2 represents a hydrogen atom or an organic group; and mb represents an integer from 1 to 6; and wherein, in formula (I-3), Y3 represents a structure represented by any one of formulas (Ex-1) to (Ex-5); and mc represents an integer from 1 to 6; wherein L1 is a single bond or a linking group; Ra an alkyl group, a halogen atom, or a fluorinated alkyl group; na is an integer from 0 to 2; nb is an integer from 1 to 3; r represents an oxygen atom or —CR2—; R represents a hydrogen atom or an alkyl group; Rb′ represents a cyclic hydrocarbon group having 4 to 20 carbon atoms in the case of mc=1, and Rb represents a hydrocarbon group having 4 to 20 carbon atoms in the case of mc-2 to 6; Rb′ may have a branched structure in the middle of the group, and a structure having -L1-* at the end thereof may be present; and * designates an atomic bonding, wherein said non-aqueous liquid electrolyte for a secondary battery further containing a compound (B) releasing, upon oxidation or reduction, an active species that reacts with the compound (A) represented by any one of formulae (I-1) to (I-3), and wherein the compound (B) comprises at least one compound selected from the group consisting of acetophenone compounds, benzophenone compounds, anthrone compounds, xanthone compounds, dibenzosuberone compounds, dibenzosuberenone compounds, anthraquinone compounds, bianthronyl compounds, bianthrone compounds, and dibenzoyl compounds. ### Claim 2 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein a content of the compound (A) is from 0.001 to 10 mass % with respect to the total amount of the liquid electrolyte. ### Claim 3 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein a content of the compound (B) is from 0.0001 to 10 mass % with respect to the total amount of the liquid electrolyte. ### Claim 4 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein an addition amount ratio (A/B) of the compound (A) to the compound (B) is from 100/1 to 1/10. ### Claim 5 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein X1 is an alkyl group substituted with a fluorine atom. ### Claim 6 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein X2 is an alkoxy group, an alkoxymethyl group, an acyloxy group, or an acyloxymethyl group. ### Claim 7 (depends on 1) A non-aqueous liquid electrolyte secondary battery, containing: a positive electrode; a negative electrode; and the non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1. ### Claim 8 (depends on 7) The non-aqueous liquid electrolyte secondary battery as claimed in claim 7, wherein a compound having at least one of nickel, cobalt, or manganese is used as an active material of the positive electrode. ### Claim 9 (depends on 7) The non-aqueous liquid electrolyte secondary batter as claimed in claim 7, wherein lithium titanate or a carbon material is used as an active material of the negative electrode. ### Claim 10 A kit of a non-aqueous liquid electrolyte for a secondary battery, wherein a chemical agent containing a compound (A) represented by any one of formulae (I-1) to (I-3) is combined with a chemical agent containing an electrolyte: wherein, in formula (I-1), X1 represents an alkyl group substituted with a halogen atom; Y1 represents a hydrogen atom or an organic group; and ma represents an integer from 1 to 6; wherein, in formula (I-2), X2 represents a group having an oxygen atom; Y2 represents a hydrogen atom or an organic group; and mb represents an integer from 1 to 6; and wherein, in formula (I-3), Y3 represents a structure represented by any one of formulas (Ex-1) to (Ex-5); and mc represents an integer from 1 to 6: wherein L1 is a single bond or a linking group; Ra an alkyl group, a halogen atom, or a fluorinated alkyl group; na is an integer from 0 to 2; nb is an integer from 1 to 3; Xa represents an oxygen atom or —CR2—; R represents a hydrogen atom or an alkyl group; Rb′ represents a cyclic hydrocarbon group having 4 to 20 carbon atoms in the case of mc=1, and Rb′ represents a hydrocarbon group having 4 to 20 carbon atoms in the case of mc=2 to 6; Rb′ may have a branched structure in the middle of the group, and a structure having -L1-* at the end thereof may be present; and * designates an atomic bonding, wherein said non-aqueous liquid electrolyte for a secondary battery further containing a compound (B) releasing, upon oxidation or reduction, an active species that reacts with the compound (A) represented by any one of formulae (I-1) to (I-3), and wherein the compound (B) comprises at least one compound selected from the group consisting of acetophenone compounds, benzophenone compounds, anthrone compounds, xanthone compounds, dibenzosuberone compounds, dibenzosuberenone compounds, anthraquinone compounds, bianthronyl compounds, bianthrone compounds, and dibenzoyl compounds. ### Claim 11 An additive for a non-aqueous secondary battery liquid electrolyte, comprising a compound (A) represented by any one of formulae (I-1) to (I-3): wherein, in formula (I-1), X1 represents an alkyl group substituted with a halogen atom; Y1 represents a hydrogen atom or an organic group; and ma represents an integer from 1 to 6; wherein, in formula (I-2), X2 represents a group having an oxygen atom; Y2 represents a hydrogen atom or an organic group; and mb represents an integer from 1 to 6; and wherein, in formula (I-3), Y3 represents a structure represented by any one of formulas (Ex-1) to (Ex-5); and mc represents an integer from 1 to 6: wherein L1 is a single bond or a linking group; Ra an alkyl group, a halogen atom, or a fluorinated alkyl group; na is an integer from 0 to 2; nb is an integer from 1 to 3; Xa represents an oxygen atom or —CR2—; R represents a hydrogen atom or an alkyl group; Rb′ represents a cyclic hydrocarbon group having 4 to 20 carbon atoms in the case of mc=1, and Rb′ represents a hydrocarbon group having 4 to 20 carbon atoms in the case of mc=2 to 6; Rb′ may have a branched structure in the middle of the group, and a structure having -L1-* at the end thereof may be present; and * designates an atomic bonding, wherein said non-aqueous liquid electrolyte for a secondary battery further containing a compound (B) releasing, upon oxidation or reduction, an active species that reacts with the compound (A) represented by any one of formulae (I-1) to (I-3), and wherein the compound (B) comprises at least one compound selected from the group consisting of acetophenone compounds, benzophenone compounds, anthrone compounds, xanthone compounds, dibenzosuberone compounds, dibenzosuberenone compounds, anthraquinone compounds, bianthronyl compounds, bianthrone compounds, and dibenzoyl compounds. ### Claim 12 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein, in formula (I-2), X2 represents an acetyloxy group, an acetyloxymethyl group, a methoxy group, a methoxymethyl group, an ethoxy group, a benzyl oxy group, or a benzoyloxymethyl group. ### Claim 13 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein, in formula (I-2), X2 represents a methoxy group, a methoxymethyl group, an ethoxy group, a benzyl oxy group, or a benzoyloxymethyl group. ### Claim 14 (depends on 1) The non-aqueous liquid electrolyte for a secondary battery as claimed in claim 1, wherein the compound (B) comprises at least one compound selected from the group consisting of acetophenone compounds, benzophenone compounds, xanthone compounds, dibenzosuberone compounds, dibenzosuberenone compounds, anthraquinone compounds, bianthronyl compounds, bianthrone compounds, and dibenzoyl compounds. ### Claim 15 (depends on 10) The kit of a non-aqueous liquid electrolyte for a secondary battery as claimed in claim 10, wherein the compound (B) comprises at least one compound selected from the group consisting of acetophenone compounds, benzophenone compounds, xanthone compounds, dibenzosuberone compounds, dibenzosuberenone compounds, anthraquinone compounds, bianthronyl compounds, bianthrone compounds, and dibenzoyl compounds. ### Claim 16 (depends on 11) The additive for a non-aqueous secondary battery liquid electrolyte as claimed in claim 11, wherein the compound (B) comprises at least one compound selected from the group consisting of acetophenone compounds, benzophenone compounds, xanthone compounds, dibenzosuberone compounds, dibenzosuberenone compounds, anthraquinone compounds, bianthronyl compounds, bianthrone compounds, and dibenzoyl compounds.