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WO2025159037A1 - Électrolyte non aqueux, batterie à électrolyte non aqueux, procédé permettant de fabriquer une batterie à électrolyte non aqueux, composé et procédé permettant de produire un composé - Google Patents

Électrolyte non aqueux, batterie à électrolyte non aqueux, procédé permettant de fabriquer une batterie à électrolyte non aqueux, composé et procédé permettant de produire un composé

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Publication number
WO2025159037A1
WO2025159037A1 PCT/JP2025/001504 JP2025001504W WO2025159037A1 WO 2025159037 A1 WO2025159037 A1 WO 2025159037A1 JP 2025001504 W JP2025001504 W JP 2025001504W WO 2025159037 A1 WO2025159037 A1 WO 2025159037A1
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WO
WIPO (PCT)
Prior art keywords
carbonate
group
nonaqueous electrolyte
general formula
electrolyte solution
Prior art date
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Pending
Application number
PCT/JP2025/001504
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English (en)
Japanese (ja)
Inventor
進 岩崎
智紀 安永
幹弘 高橋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Central Glass Co Ltd
Original Assignee
Central Glass Co Ltd
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Application filed by Central Glass Co Ltd filed Critical Central Glass Co Ltd
Publication of WO2025159037A1 publication Critical patent/WO2025159037A1/fr
Pending legal-status Critical Current
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0568—Liquid materials characterised by the solutes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0569—Liquid materials characterised by the solvents
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/058—Construction or manufacture
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • This disclosure relates to nonaqueous electrolytes, nonaqueous electrolyte batteries, methods for manufacturing nonaqueous electrolyte batteries, compounds, and methods for manufacturing compounds.
  • Patent Document 1 discloses a nonaqueous electrolyte for lithium batteries to which a phosphonic acid compound has been added as a nonaqueous electrolyte that improves cycle characteristics and storage properties.
  • Patent Document 2 discloses a nonaqueous electrolyte to which a specific phosphate ester compound having a double bond has been added as a nonaqueous electrolyte that suppresses gas generation and has excellent cycle characteristics.
  • the present disclosure has been made in light of the above circumstances, and aims to provide a nonaqueous electrolyte, a nonaqueous electrolyte battery, and a method for manufacturing a nonaqueous electrolyte battery that significantly suppresses gas generation during high-temperature storage tests. It also aims to provide a compound that can be suitably used in the nonaqueous electrolyte, and a method for manufacturing the compound.
  • the present invention is as follows:
  • (II) includes at least one selected from the group consisting of a cyclic ester, a chain ester, a cyclic ether, a chain ether, a sulfone compound, a sulfoxide compound, and an ionic liquid.
  • the cyclic carbonate includes at least one selected from the group consisting of ethylene carbonate and propylene carbonate.
  • R represents an alkenyl group or an alkynyl group
  • X represents an alkylene group, an alkenylene group, an alkynylene group, or an arylene group.
  • R in the compound represented by general formula (1) is an allyl group or a 2-propynyl group.
  • X in the compound represented by general formula (1) is an alkylene group.
  • the method includes a step of reacting a compound represented by the following general formula (2) with a compound represented by the following general formula (3):
  • Each R 11 is independently an alkenyl group or an alkynyl group.
  • A is a halogen atom.
  • Q is a single bond, an alkylene group, an alkenylene group, an alkynylene group, or an arylene group.
  • R 12 is a hydrogen atom or a monovalent substituent.
  • This disclosure provides a nonaqueous electrolyte that, when used in a nonaqueous electrolyte battery, can significantly suppress gas generation during high-temperature storage tests, a nonaqueous electrolyte battery, and a method for manufacturing a nonaqueous electrolyte battery. It also provides a compound that is suitable for use in the nonaqueous electrolyte, and a method for manufacturing the compound.
  • a nonaqueous electrolyte containing (III) When a nonaqueous electrolyte containing (III) is used in a nonaqueous electrolyte battery (e.g., a lithium-ion secondary battery or a sodium-ion secondary battery), (III) decomposes at least on either the positive electrode or the negative electrode, and a polymerization reaction proceeds from the alkenyl or alkynyl group portion of R in the compound represented by general formula (1), forming a strong, heat-resistant coating. Therefore, it is believed that during high-temperature storage tests, decomposition of the solvent, which is a source of gas generation, can be suppressed without the coating becoming brittle. The inventors estimate that, as a result, gas generation during high-temperature storage tests can be significantly suppressed.
  • a nonaqueous electrolyte battery e.g., a lithium-ion secondary battery or a sodium-ion secondary battery
  • (III) decomposes at least on either the
  • Such a solute is preferably an ionic salt formed from a pair of at least one cation selected from the group consisting of alkali metal ions such as lithium ions and sodium ions, alkaline earth metal ions, and quaternary ammonium ions, and at least one anion selected from the group consisting of hexafluorophosphate anion, tetrafluoroborate anion, hexafluoroantimonate anion, hexafluoroarsenate anion, perchlorate anion, bis(fluorosulfonyl)imide anion, aluminate anion, tetrachloroaluminate anion, chloride ion, and iodide ion.
  • alkali metal ions such as lithium ions and sodium ions, alkaline earth metal ions, and quaternary ammonium ions
  • anion selected from the group consisting of hexafluorophosphate anion, tetraflu
  • At least one selected from the group consisting of LiPF6, LiBF4 , LiSbF6 , LiAsF6 , LiClO4 , LiN( SO2F ) 2 , LiAlO2 , LiAlCl4 , LiCl, and LiI can be preferably mentioned.
  • the nonaqueous electrolyte solution of the present disclosure may use one type of compound alone as (I), or two or more types of compounds may be mixed in any combination and ratio depending on the application.
  • the concentration of (I) relative to the total amount of non-aqueous electrolyte.
  • the lower limit of the concentration of (I) may be 0.5 mol/L or more, 0.7 mol/L or more, or 0.9 mol/L or more.
  • the upper limit of the concentration of (I) may be 5 mol/L or less, 4 mol/L or less, or 2 mol/L or less.
  • a concentration of 0.5 mol/L or more is preferred because it reduces the likelihood of a decrease in ionic conductivity and a decrease in the cycle characteristics and output characteristics of the non-aqueous electrolyte battery.
  • a concentration of 5 mol/L or less is preferred because it reduces the likelihood of an increase in the viscosity of the non-aqueous electrolyte and a decrease in ionic conductivity.
  • the total concentration of these solutes be within the above-mentioned range.
  • the liquid temperature when (I) is dissolved in (II) the nonaqueous organic solvent is not particularly limited, but may be from -20 to 80°C or from 0 to 60°C.
  • the cation of the solute is more preferably a lithium ion when used in a lithium ion battery, and more preferably a sodium ion when used in a sodium ion battery.
  • Non-aqueous organic solvent (also referred to as "(II)") contained in the nonaqueous electrolyte solution of the present disclosure will be described.
  • the type of nonaqueous organic solvent (II) is not particularly limited, and any nonaqueous organic solvent can be used.
  • Such a nonaqueous organic solvent preferably contains at least one selected from the group consisting of cyclic esters, chain esters, cyclic ethers, chain ethers, sulfone compounds, sulfoxide compounds, amide compounds, nitrile compounds, and ionic liquids, and more preferably contains at least one selected from the group consisting of cyclic esters, chain esters, cyclic ethers, chain ethers, sulfone compounds, sulfoxide compounds, and ionic liquids.
  • cyclic carbonates are a sub-concept of cyclic esters
  • chain carbonates are a sub-concept of chain esters.
  • nonaqueous organic solvent examples include the following nonaqueous organic solvents.
  • cyclic esters include cyclic carbonates such as propylene carbonate (hereinafter sometimes referred to as "PC"), ethylene carbonate (hereinafter sometimes referred to as “EC”), and butylene carbonate, as well as ⁇ -butyrolactone and ⁇ -valerolactone.
  • PC propylene carbonate
  • EC ethylene carbonate
  • butylene carbonate as well as ⁇ -butyrolactone and ⁇ -valerolactone.
  • chain ester examples include diethyl carbonate (hereinafter sometimes referred to as "DEC”), dimethyl carbonate (hereinafter sometimes referred to as “DMC”), ethyl methyl carbonate (hereinafter sometimes referred to as “EMC”), methyl propyl carbonate, ethyl propyl carbonate, methyl butyl carbonate, 2,2,2-trifluoroethyl methyl carbonate, 2,2,2-trifluoroethyl ethyl carbonate, 2,2,2-trifluoroethyl propyl carbonate, In addition to chain carbonates such as 1,1,1,3,3,3-hexafluoro-1-propylmethyl carbonate, 1,1,1,3,3,3-hexafluoro-1-propylethyl carbonate, and 1,1,1,3,3,3-hexafluoro-1-propylpropyl carbonate, methyl acetate, ethyl acetate, methyl propionate, ethyl propionate
  • cyclic ethers include tetrahydrofuran, 2-methyltetrahydrofuran, furan, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, 1,3-dioxolane, and trioxane.
  • chain ethers include diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, dimethoxymethane, trimethoxymethane, 1,2-dimethoxyethane, diethoxyethane, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.
  • sulfone compounds such as dimethyl sulfoxide and sulfolane
  • sulfoxide compounds N,N-dimethylformamide
  • acetonitrile propionitrile
  • ionic liquids and the like can also be used.
  • the nonaqueous organic solvent may contain at least one selected from the group consisting of cyclic esters, chain esters, cyclic ethers, chain ethers, sulfone compounds, sulfoxide compounds, and ionic liquids.
  • the cyclic ester may contain a cyclic carbonate, and the cyclic carbonate may contain at least one selected from the group consisting of ethylene carbonate and propylene carbonate.
  • the chain ester may include a chain carbonate, and the chain carbonate may include at least one selected from the group consisting of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, and methyl propyl carbonate.
  • the cyclic ether may include at least one selected from the group consisting of tetrahydrofuran, 2-methyltetrahydrofuran, furan, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, 1,3-dioxolane, and trioxane.
  • the chain ether may include at least one selected from the group consisting of diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, dimethoxymethane, trimethoxymethane, 1,2-dimethoxyethane, diethoxyethane, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.
  • the nonaqueous electrolyte solution of the present disclosure may use one type of compound alone as (II), or two or more types of compounds may be mixed in any combination and ratio depending on the application.
  • the nonaqueous organic solvent contains, for example, one or more cyclic carbonates having a high dielectric constant and one or more chain carbonates or chain esters having a low liquid viscosity, since this increases the ionic conductivity of the electrolyte solution.
  • a nonaqueous organic solvent containing the following combinations: (1) Combination of EC and EMC, (2) A combination of EC and DEC, (3) A combination of EC, DMC, and EMC; (4) A combination of EC, DEC, and EMC; (5) A combination of EC, EMC, and EP; (6) A combination of PC and DEC, (7) Combination of PC and EMC, (8) A combination of PC and EP, (9) A combination of PC, DMC, and EMC; (10) Combination of PC, DEC and EMC, (11) A combination of PC, DEC, and EP, (12) Combination of PC, EC and EMC; (13) A combination of PC, EC, DMC, and EMC; (14) A combination of PC, EC, DEC, and EMC; (15) Combination of PC, EC, EMC, and EP
  • the content of the cyclic carbonate is not particularly limited and can be any amount as long as it does not significantly impair the effects of the present disclosure. However, when one type is used alone, the content may be 3 vol.% or more, and more preferably 5 vol.% or more, based on 100 vol.% of the nonaqueous organic solvent. By keeping the content within this range, a decrease in electrical conductivity resulting from a decrease in the dielectric constant of the nonaqueous electrolyte can be avoided, and the large current discharge characteristics, stability with respect to the negative electrode, and cycle characteristics of the nonaqueous electrolyte battery can be easily maintained within good ranges.
  • the content may also be 90 vol.% or less, preferably 85 vol.% or less, and more preferably 80 vol.% or less.
  • the ethyl methyl carbonate content may be 20% by volume or more, preferably 30% by volume or more, and 50% by volume or less, preferably 45% by volume or less.
  • the content of the chain ether is not particularly limited and may be any amount as long as it does not significantly impair the effects of the present disclosure. However, it may be 1% by volume or more, preferably 2% by volume or more, more preferably 3% by volume or more, and 30% by volume or less, preferably 25% by volume or less, and more preferably 20% by volume or less, based on 100% by volume of the nonaqueous organic solvent. If the content of the chain ether is within the above range, for example, in the case of a lithium-ion battery in which the cation is mainly lithium, it is easy to ensure the improved ionic conductivity resulting from the improved lithium ion dissociation degree of the chain ether and the reduced viscosity. Furthermore, when the negative electrode active material is a carbonaceous material, the phenomenon of the chain ether being co-inserted with lithium ions can be suppressed, making it easier to maintain the input/output characteristics and charge/discharge rate characteristics within appropriate ranges.
  • the content of the sulfone compound is not particularly limited and can be any content as long as it does not significantly impair the effects of the present disclosure, but may be 0.3 vol% or more, preferably 0.5 vol% or more, more preferably 1 vol% or more, and may be 40 vol% or less, preferably 35 vol% or less, more preferably 30 vol% or less, based on 100 vol% of the nonaqueous organic solvent.
  • the content of the sulfone compound is within the above range, it is easy to obtain improved durability such as cycle characteristics and storage characteristics, and it is also possible to maintain the viscosity of the nonaqueous electrolyte within an appropriate range, avoid a decrease in electrical conductivity, and make it easier to maintain the input/output characteristics and charge/discharge rate characteristics of the nonaqueous electrolyte battery within appropriate ranges.
  • the alkenyl group represented by R includes linear or branched alkenyl groups having 2 to 6 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl, 1,3-butadienyl, 4-pentenyl, and 5-hexenyl.
  • the alkynyl group represented by R includes linear or branched alkynyl groups having 2 to 6 carbon atoms, such as ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl, 4-pentynyl, and 5-hexynyl.
  • R is preferably a vinyl group, an allyl group, a 2-propynyl group, a 3-butenyl group, or a 3-butynyl group, and more preferably an allyl group or a 2-propynyl group.
  • the alkylene group represented by X includes linear or branched alkylene groups having 1 to 6 carbon atoms, such as methylene, ethylene, 1-methylethylene, 2-methylethylene, 1,2-dimethylethylene, n-propylene, n-butylene, and n-hexylene.
  • the alkenylene group represented by X includes linear or branched alkenylene groups having 2 to 6 carbon atoms, such as vinylene, 1-propenylene, 2-propenylene, isopropenylene, 2-butenylene, 3-butenylene, 1,3-butadienylene, 2-pentenylene, and 3-hexenylene.
  • the alkynylene group represented by X includes linear or branched alkynylene groups having 2 to 6 carbon atoms, such as ethynylene, 1-propynylene, 2-butynylene, 2-pentynylene, and 3-hexynylene.
  • the arylene group represented by X includes an arylene group having 6 to 8 carbon atoms, specifically a phenylene group, a tolylene group, a xylylene group, etc.
  • At least one of the hydrogen atoms in the alkylene group, alkenylene group, alkynylene group, and arylene group may be substituted with a substituent, such as a fluorine atom or an alkoxy group (a linear or branched alkoxy group having 1 to 6 carbon atoms).
  • a substituent such as a fluorine atom or an alkoxy group (a linear or branched alkoxy group having 1 to 6 carbon atoms).
  • X is an alkylene group.
  • X is preferably an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a phenylene group, and more preferably an ethylene group.
  • the content of the component (III) (hereinafter also referred to as the "concentration of (III)") relative to the total amount (100 mass%) of the nonaqueous electrolyte solution is preferably 0.005 mass% or more, more preferably 0.05 mass% or more, and even more preferably 0.1 mass% or more.
  • the upper limit of the concentration of (III) is preferably 10.0 mass% or less, more preferably 5.0 mass% or less, even more preferably 4.0 mass% or less, and particularly preferably 2.5 mass% or less.
  • the content of the component (III) relative to the total amount of the non-aqueous electrolyte is preferably 0.005 to 10.0% by mass, more preferably 0.005 to 5.0% by mass, and even more preferably 0.05 to 5.0% by mass.
  • the nonaqueous electrolyte solution (III) of the present disclosure may use one type of compound alone, or two or more types of compounds mixed in any combination and ratio depending on the application.
  • the compound represented by general formula (1) can be produced by known methods.
  • the present disclosure also provides a method for producing a compound represented by the following general formula (2), comprising reacting a compound represented by the following general formula (3):
  • the present invention also relates to a method for producing a compound represented by the following general formula (1A):
  • Each R 11 is independently an alkenyl group or an alkynyl group.
  • A is a halogen atom.
  • Q is a single bond, an alkylene group, an alkenylene group, an alkynylene group, or an arylene group.
  • R 12 is a hydrogen atom or a monovalent substituent.
  • the alkenyl group in R 11 is the same as the alkenyl group in R in the general formula (1), and the preferred range is also the same.
  • the alkynyl group in R 11 is the same as the alkynyl group in R in the general formula (1), and the preferred range is also the same.
  • Examples of the halogen atom of A include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom being preferred.
  • the alkylene group represented by Q includes linear or branched alkylene groups having 1 to 6 carbon atoms (preferably 1 to 4 carbon atoms), specifically including methylene, ethylene, 1-methylethylene, 2-methylethylene, 1,2-dimethylethylene, n-propylene, n-butylene, and n-hexylene.
  • the alkenylene group represented by Q includes linear or branched alkenylene groups having 2 to 6 carbon atoms (preferably 2 to 4 carbon atoms), specifically including vinylene, 1-propenylene, 2-propenylene, isopropenylene, 2-butenylene, 3-butenylene, 1,3-butadienylene, 2-pentenylene, and 3-hexenylene.
  • the alkynylene group represented by Q includes linear or branched alkynylene groups having 2 to 6 carbon atoms (preferably 2 to 4 carbon atoms), and specific examples include ethynylene, 1-propynylene, 2-butynylene, 2-pentynylene, and 3-hexynylene.
  • the arylene group represented by Q includes an arylene group having 6 to 8 carbon atoms (6 carbon atoms is preferred), and specific examples include a phenylene group, a tolylene group, and a xylylene group.
  • At least one of the hydrogen atoms in the alkylene group, alkenylene group, alkynylene group, and arylene group may be substituted with a substituent.
  • substituents include a fluorine atom and an alkoxy group (a linear or branched alkoxy group having 1 to 6 carbon atoms).
  • Q is preferably a single bond or an alkylene group.
  • the monovalent substituent of R 12 is not particularly limited, but examples thereof include an alkyl group (specifically, a linear or branched alkyl group having 1 to 6 carbon atoms), an alkoxy group (a linear or branched alkoxy group having 1 to 6 carbon atoms), and a fluorine atom.
  • Step A The step of reacting the compound represented by the above general formula (2) with the compound represented by the above general formula (3) (also referred to as step A) will be described.
  • the content of the compound represented by the general formula (3) is preferably 1.0 mol to 5.0 mol, and more preferably 1.0 mol to 2.0 mol, relative to 1 mol of the compound represented by the general formula (2).
  • Step A is preferably carried out in a non-aqueous organic solvent.
  • the non-aqueous organic solvent include acetonitrile, acetone, 1,2-dimethoxyethane, ethyl acetate, tetrahydrofuran, toluene, dimethyl carbonate, and ethyl methyl carbonate, with acetonitrile being preferred.
  • the reaction temperature in step A is not particularly limited, but is preferably 25 to 120°C, and more preferably 40 to 90°C.
  • the reaction time in step A is not particularly limited, but is preferably 1 to 96 hours, and more preferably 6 to 48 hours.
  • the compound represented by the general formula (2) reacts with the compound represented by the general formula (3), and then a cyclization reaction takes place intramolecularly, thereby synthesizing the compound represented by the general formula (1A).
  • the nonaqueous electrolyte solution of the present disclosure is composed of the above-mentioned components as basic constituents, but the nonaqueous electrolyte solution of the present disclosure may contain the components described below (hereinafter also referred to as "other components that may be contained” or “other components") in any combination and ratio as long as the gist of the present disclosure is not impaired.
  • other components for example, other additives commonly used in this technical field may be added in any ratio.
  • ingredients include, for example: aromatic compounds such as cyclohexylbenzene, cyclohexylfluorobenzene, biphenyl, 2-fluorobiphenyl, tert-butylbenzene, tert-amylbenzene, 2-fluorotoluene, fluorobenzene, and difluoroanisole; carbonate compounds such as vinylene carbonate (hereinafter sometimes referred to as "VC"), vinylene carbonate oligomers (having a number average molecular weight of 170 to 5000 in terms of polystyrene), vinyl ethylene carbonate, divinyl ethylene carbonate, fluoroethylene carbonate (hereinafter sometimes referred to as "FEC”), ethynyl ethylene carbonate, trans-difluoroethylene carbonate, methyl propargyl carbonate, ethyl propargyl carbonate, dipropargyl carbonate, dimethyl vinylene carbonate, dimethyl dicarbonate,
  • nonaqueous electrolyte solution of the present disclosure may further contain the following compounds to improve cycle capacity retention and gas generation during cycle testing.
  • the nonaqueous electrolyte solution of the present disclosure further includes cyclohexylbenzene, cyclohexylfluorobenzene, biphenyl, 2-fluorobiphenyl, tert-butylbenzene, tert-amylbenzene, 2-fluorotoluene, fluorobenzene, difluoroanisole, Vinylene carbonate, vinylene carbonate oligomer (number average molecular weight in terms of polystyrene of 170 to 5000), vinyl ethylene carbonate, divinyl ethylene carbonate, fluoroethylene carbonate, ethynyl ethylene carbonate, trans-difluoroethylene carbonate, methyl propargyl carbonate, ethyl propargyl carbonate, dipropargyl carbonate, dimethyl vinylene carbonate, dimethyl dicarbonate, bis(1,1,3,3,3-hexafluoro-1-propyl)carbonate, bis(2,2,2-
  • At least one of the following effects may be enhanced: overcharge prevention, negative electrode film formation, and positive electrode protection.
  • non-aqueous electrolyte batteries known as lithium polymer batteries
  • electrolytes for non-aqueous electrolyte batteries that have been quasi-solidified using a gelling agent or cross-linked polymer.
  • polymers include polymers with polyethylene oxide in the main chain or side chain, polyvinylidene fluoride homopolymers or copolymers, methacrylic acid ester polymers, and polyacrylonitrile.
  • the content of the other components may be 0.01% by mass or more and 10% by mass or less with respect to the total amount of the non-aqueous electrolyte solution.
  • the content of fluoroethylene carbonate may be 0.01% by mass or more and 55% by mass or less relative to the total amount of the nonaqueous electrolyte solution.
  • the content of bis(trifluoromethanesulfonyl)imide salt, trifluoromethanesulfonate salt, and nonafluorobutanesulfonate salt relative to the total amount of the nonaqueous electrolyte may be 0.01% by mass or more and 20% by mass or less.
  • the content of bis(1,1,1,3,3,3-hexafluoro-1-propyl) carbonate and bis(2,2,2-trifluoroethyl) carbonate relative to the total amount of the nonaqueous electrolyte may be 0.1 mass % or more and 70.0 mass % or less.
  • the cations are preferably lithium ions when used in lithium-ion batteries, and more preferably sodium ions when used in sodium-ion batteries.
  • the nonaqueous electrolyte solution of the present disclosure may contain a total of four or more alkali metal salts by using multiple types of the above solutes (lithium salts, sodium salts, etc.) and salt compounds of the other components, depending on the required characteristics. Also, the total of five or more alkali metal salts may be used.
  • nonaqueous electrolyte solution disclosed herein is suitable for use in nonaqueous electrolyte batteries (preferably nonaqueous electrolyte secondary batteries).
  • the non-aqueous electrolyte battery of the present disclosure includes at least the non-aqueous electrolyte of the present disclosure, a negative electrode, and a positive electrode. It may also include a separator, an exterior body, etc. Alternatively, a solid electrolyte may be used as a medium for impregnating the non-aqueous electrolyte instead of the separator.
  • the nonaqueous electrolyte battery of the present disclosure preferably includes at least a positive electrode, a negative electrode, and the nonaqueous electrolyte of the present disclosure.
  • the nonaqueous electrolyte battery of the present disclosure is preferably a nonaqueous electrolyte secondary battery.
  • the negative electrode is not particularly limited, but may be made of a material that allows reversible insertion and desorption of alkali metal ions such as lithium ions and sodium ions, or alkaline earth metal ions.
  • the negative electrode active material constituting the negative electrode is one that can be doped and dedoped with lithium ions, and examples thereof include carbon materials such as artificial graphite and natural graphite, in which the d value of the lattice plane (002) in X-ray diffraction is 0.340 nm or less, carbon materials such as hard carbon, in which the d value of the lattice plane (002) in X-ray diffraction is greater than 0.340 nm, lithium metal, alloys of lithium metal and other metals (e.g., alloys of lithium metal with one or more metals selected from Si, Sn, and Al, alloys of lithium metal with alloys containing one or more metals selected from Si, Sn, and Al), intermetallic compounds of lithium metal and other metals, metal oxides (e.g., oxides of one or more metals selected from Si, Sn, and
  • a suitable negative electrode active material may include a material containing Si and/or Si metal oxide and a carbon material.
  • the Si is silicon metal.
  • the Si metal oxide may be a compound represented by SiOx (where x is a value between 0.5 and 1.5).
  • the total content of Si and/or Si metal oxide contained in the negative electrode active material may be 0.1 to 50% by mass, preferably 0.1 to 30% by mass, based on 100% by mass of the total amount of the Si and/or Si metal oxide and the carbon material contained in the negative electrode active material.
  • Graphite is preferred as the carbon material, and various types of artificial graphite, natural graphite, and hard carbon (non-graphitizable carbon) can be used.
  • Graphite exhibits minimal change in its crystalline structure due to the absorption and desorption of lithium, resulting in high energy density and excellent cycle characteristics.
  • the shape of the graphite may be fibrous, spherical, granular, or flake-like.
  • amorphous carbon and graphite coated with amorphous carbon are more preferable because they have a lower reactivity between the material surface and the electrolyte.
  • These negative electrode active materials can be used alone or in combination of two or more.
  • the negative electrode active material that constitutes the negative electrode may be sodium metal, an alloy of sodium metal with other metals such as tin, an intermetallic compound of sodium metal with other metals, various carbon materials such as hard carbon, metal oxides such as titanium oxide, metal nitrides, tin (elementary), tin compounds, activated carbon, conductive polymers, etc.
  • phosphorus such as red phosphorus and black phosphorus
  • phosphorus compounds such as Co-P, Cu-P, Sn-P, Ge-P, and Mo-P
  • antimony elementary
  • antimony compounds such as Sb/C and Bi-Sb, etc.
  • These negative electrode active materials may be used alone or in combination of two or more.
  • the negative electrode has a negative electrode current collector.
  • the negative electrode current collector include copper, stainless steel, nickel, titanium, and alloys thereof.
  • aluminum and its alloys can also be used.
  • the negative electrode has, for example, a negative electrode active material layer formed on at least one surface of a negative electrode current collector.
  • the negative electrode active material layer is composed of, for example, the above-mentioned negative electrode active material, a binder, and, if necessary, a conductive agent.
  • binders include polytetrafluoroethylene, polyvinylidene fluoride, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, styrene butadiene rubber (hereinafter also referred to as "SBR"), carboxymethyl cellulose, methyl cellulose, cellulose acetate phthalate, hydroxypropyl methyl cellulose, polyvinyl alcohol, and polyimide.
  • SBR styrene butadiene rubber
  • carboxymethyl cellulose carboxymethyl cellulose
  • methyl cellulose methyl cellulose
  • cellulose acetate phthalate hydroxypropyl methyl cellulose
  • polyvinyl alcohol polyimide
  • the conductive agent for example, carbon materials such as acetylene black, ketjen black, furnace black, carbon fiber, graphite, and fluorinated graphite can be used.
  • the positive electrode is not particularly limited, but may be made of a material that allows reversible insertion and desorption of alkali metal ions such as lithium ions and sodium ions, or alkaline earth metal ions.
  • the positive electrode material when the cation is lithium, the positive electrode material (positive electrode active material) may be a lithium-containing transition metal composite oxide such as LiCoO 2 , LiNiO 2 , LiMnO 2 , or LiMn 2 O 4 ; a mixture of these lithium-containing transition metal composite oxides with multiple transition metals such as Co, Mn, or Ni; or a lithium-containing transition metal composite oxide in which part of the transition metal has been substituted with a metal other than the transition metal.
  • a lithium-containing transition metal composite oxide such as LiCoO 2 , LiNiO 2 , LiMnO 2 , or LiMn 2 O 4
  • a mixture of these lithium-containing transition metal composite oxides with multiple transition metals such as Co, Mn, or Ni
  • a lithium-containing transition metal composite oxide in which part of the transition metal has been substituted with a metal other than the transition metal when the cation is lithium, the positive electrode material (positive electrode active material) may be a lithium-containing transition metal composite oxide such as
  • Li[Ni1 /3Mn1 / 3Co1/ 3 ]O2 Li [ Ni0.45Mn0.35Co0.2 ] O2 , Li[ Ni0.5Mn0.3Co0.2 ] O2 , Li[ Ni0.6Mn0.2Co0.2 ] O2 (hereinafter, sometimes referred to as "NCM622"), Li[ Ni0.8Mn0.1Co0.1 ] O2 ( hereinafter, sometimes referred to as " NCM811") , Li [ Ni0.49Mn0.3Co0.2Zr0.01 ] O2 , Li [ Ni0.49Mn0.3Co0.2Zr0.01 ] O2 0.2 Mg 0.01 ]O 2 , LiNi 0.8 Co 0.2 O 2 , LiNi 0.85 Co 0.10 Al 0.05 O 2 , LiNi 0.87 Co 0.10 Al 0.03 O 2 , LiNi 0.90 Co 0.07 Al 0.03 O 2 , LiNi 0.6 Co 0.3 Al 0.1 O 2, LiNi 0.5 Mn 1.5 O 4, LiNi 0.5 Mn 0.5 0.5
  • phosphate compounds of transition metals called olivine such as LiFePO4 , LiCoPO4 , LiMnPO4 , and LiNiPO4 , oxides such as TiO2 , V2O5 , and MoO3 , sulfides such as TiS2 , FeS, and MoS2 , conductive polymers such as polyacetylene, polyparaphenylene, polyaniline , and polypyrrole, activated carbon, radical-generating polymers, and carbon materials may be used.
  • olivine such as LiFePO4 , LiCoPO4 , LiMnPO4 , and LiNiPO4
  • oxides such as TiO2 , V2O5 , and MoO3
  • sulfides such as TiS2 , FeS, and MoS2
  • conductive polymers such as polyacetylene, polyparaphenylene, polyaniline , and polypyrrole, activated carbon, radical-generating polymers, and carbon materials
  • examples of the positive electrode material include NaCrO2 , NaFe0.5Co0.5O2 , NaFe0.4Mn0.3Ni0.3O2 , NaNi0.5Ti0.3Mn0.2O2 , NaNi1 /3Ti1 / 3Mn1 / 3O2 , NaNi0.33Ti0.33Mn0.16Mg0.17O2 , Na2 / 3Ni1/ 3Ti1 / 6Mn1/ 2O2 , and Na2 /3Ni1 / 3Mn2 / 3O .
  • the positive electrode has a positive electrode current collector, which may be made of, for example, aluminum, stainless steel, nickel, titanium, or an alloy thereof.
  • the positive electrode has a positive electrode active material layer formed on at least one surface of a positive electrode current collector, for example.
  • the positive electrode active material layer is composed of, for example, the above-mentioned positive electrode active material, a binder, and, if necessary, a conductive agent.
  • the binder include those described in the negative electrode active material layer.
  • the conductive agent that can be used include carbon materials such as acetylene black, ketjen black, furnace black, carbon fiber, graphite (granular graphite or flake graphite), and fluorinated graphite.
  • the electrode can be obtained, for example, by dispersing and kneading a predetermined amount of an active material, a binder, and, if necessary, a conductive agent in a solvent such as N-methyl-2-pyrrolidone (NMP) or water, applying the resulting paste to a current collector, and drying to form an active material layer.
  • NMP N-methyl-2-pyrrolidone
  • the resulting electrode is preferably compressed by a method such as a roll press to adjust the electrode to an appropriate density.
  • the nonaqueous electrolyte battery of the present disclosure may include a separator.
  • the separator which prevents contact between the positive electrode and the negative electrode, may be, for example, a nonwoven fabric or porous sheet made of polyolefins such as polypropylene or polyethylene, cellulose, paper, or glass fiber. These films are preferably microporous so that the electrolyte can penetrate and ions can easily pass through.
  • polyolefin separators include microporous polymer films such as porous polyolefin films, which electrically insulate the positive and negative electrodes and are permeable to lithium ions.
  • porous polyolefin films include porous polyethylene films alone, or multilayer films formed by stacking porous polyethylene films and porous polypropylene films. Other examples include composite films of porous polyethylene and polypropylene films.
  • the nonaqueous electrolyte solution of the present disclosure may be impregnated into the separator and held therein.
  • the impregnation method is not particularly limited, and may be carried out by a known method. Specifically, the impregnation can be achieved by finally injecting the electrolyte solution into a battery including a positive electrode, a separator, and a negative electrode.
  • Suitable exterior bodies for the nonaqueous electrolyte battery of the present disclosure include, for example, coin-shaped, cylindrical, and rectangular metal cans, as well as laminated exterior bodies.
  • Suitable metal can materials include, for example, nickel-plated steel, stainless steel, nickel-plated stainless steel, aluminum or its alloys, nickel, and titanium.
  • Suitable laminate exterior bodies include, for example, aluminum laminate films, SUS laminate films, and laminate films of silica-coated polypropylene, polyethylene, and the like.
  • the configuration of the nonaqueous electrolyte battery according to this embodiment is not particularly limited, but for example, it can be configured such that an electrode element in which a positive electrode and a negative electrode are arranged opposite each other, and a nonaqueous electrolyte are enclosed in an exterior body.
  • the shape of the nonaqueous electrolyte battery is not particularly limited, but an electrochemical device in the shape of a coin, cylinder, square, aluminum laminate sheet, or the like can be assembled from the above elements.
  • R is an alkenyl group or an alkynyl group
  • X is an alkylene group, an alkenylene group, an alkynylene group, or an arylene group.
  • the compound represented by the general formula (1) above is the same as (III) in the nonaqueous electrolyte solution of the present disclosure, and the above explanation can be used as is for details of the compound and the method for producing the compound.
  • R is preferably an allyl group, a 2-propynyl group, a 3-butenyl group, or a 3-butynyl group, and more preferably an allyl group or a 2-propynyl group.
  • X is preferably an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a phenylene group, and more preferably an ethylene group.
  • the method for manufacturing a non-aqueous electrolyte battery according to the present disclosure includes a step of injecting the non-aqueous electrolyte according to the present disclosure.
  • the method for injecting the electrolyte is not particularly limited, and can be a conventional method. For example, vacuum injection can be used.
  • LiPF 6 was dissolved as a solute to a concentration of 1.0 mol/L relative to the total amount of the electrolyte, and at least one compound selected from the group consisting of compounds represented by general formula (1) (hereinafter sometimes referred to as "component (III)") or a comparative compound was dissolved in the amount shown in Tables 1 to 8 below relative to the total amount of the electrolyte.
  • component (III) compounds represented by general formula (1)
  • a positive electrode composite paste was prepared by mixing 90% by weight of LiNi0.6Co0.2Mn0.2O2 powder with 5% by weight of polyvinylidene fluoride (PVDF) as a binder and 5% by weight of acetylene black as a conductive material, and then adding N-methyl-2-pyrrolidone.
  • PVDF polyvinylidene fluoride
  • This paste was applied to both sides of aluminum foil (A1085), dried, pressed, and then punched out to a 4 cm x 5 cm piece to obtain a test NCM622 positive electrode.
  • a slurry solution was prepared by mixing 92% by mass of natural graphite powder, 3% by mass of a conductive material (HS-100), 2% by mass of carbon nanofiber (VGCF), 2% by mass of styrene-butadiene rubber, 1% by mass of sodium carboxymethyl cellulose, and water. This slurry solution was applied to a copper foil negative electrode current collector and dried at 100°C for 12 hours to obtain a test natural graphite negative electrode having a negative electrode active material layer formed on the current collector.
  • HS-100 a conductive material
  • VGCF carbon nanofiber
  • a slurry solution was prepared by mixing 85% by mass of artificial graphite powder, 7% by mass of nanosilicon, 3% by mass of conductive material (HS-100), 2% by mass of carbon nanofiber (VGCF), 2% by mass of styrene-butadiene rubber, 1% by mass of sodium carboxymethyl cellulose, and water. This slurry solution was applied to a copper foil negative electrode current collector and dried at 100°C for 12 hours to obtain a silicon-containing graphite negative electrode for testing, in which a negative electrode active material layer was formed on the current collector.
  • NaPF6 was dissolved as a solute to a concentration of 1.0 mol/L relative to the total amount of the electrolyte
  • component (III) or a comparative compound was dissolved in the amount shown in Tables 17 to 24 below relative to the total amount of the electrolyte.
  • the compounds shown in Tables 18 to 24 below were similarly dissolved in the amount shown. The above preparation was carried out at 25°C.
  • BOB-Na represents sodium bis(oxalato)borate
  • DFBOP-Na represents sodium difluorobis(oxalato)phosphate
  • TFOP-Na represents sodium tetrafluorooxalatophosphate
  • FSI-Na represents sodium bis(fluorosulfonyl)imide
  • DFP-Na represents sodium difluorophosphate
  • FS-Na represents sodium fluorosulfonate.
  • a slurry solution was prepared by mixing 90% by mass of hard carbon powder (Carbotron P, manufactured by Kureha Corporation) and 10% by mass of PVDF as a binder, and then adding N-methylpyrrolidone as a solvent in an amount of 50% by mass relative to the total mass of the negative electrode active material and binder.
  • This slurry solution was applied to an aluminum foil negative electrode current collector and dried at 150°C for 12 hours to obtain a test hard carbon negative electrode having a negative electrode active material layer formed on the current collector.
  • the aluminum laminate - type nonaqueous electrolyte batteries of the Examples and Comparative Examples in Tables 17 to 24 were fabricated in the same manner as the aluminum laminate-type nonaqueous electrolyte batteries of the Examples and Comparative Examples in Tables 1 to 8, except that the NCM622 positive electrode and natural graphite negative electrode were replaced with the above-mentioned NaNi0.5Ti0.3Mn0.2O2 positive electrode and hard carbon negative electrode, respectively.
  • the battery was placed in a thermostatic chamber at 25°C and connected to a charge/discharge device in that state. It was charged to 4.2 V at a charge rate of 0.2 C (a current value that would result in a full charge in 5 hours). After maintaining 4.2 V for 1 hour, it was discharged to 3.0 V at a discharge rate of 0.2 C. This constituted one charge/discharge cycle, and a total of 10 charge/discharge cycles were performed to stabilize the battery.
  • the gas amounts (amounts of gas generated during high-temperature storage tests) in Tables 1 to 24 are relative values when Comparative Example 1-1, Comparative Example 2-1, Comparative Example 3-1, Comparative Example 4-1, Comparative Example 5-1, Comparative Example 6-1, Comparative Example 7-1, Comparative Example 8-1, Comparative Example 9-1, Comparative Example 10-1, Comparative Example 11-1, Comparative Example 12-1, Comparative Example 13-1, Comparative Example 14-1, Comparative Example 15-1, Comparative Example 16-1, Comparative Example 17-1, Comparative Example 18-1, Comparative Example 19-1, Comparative Example 20-1, Comparative Example 21-1, Comparative Example 22-1, Comparative Example 23-1, and Comparative Example 24-1 are set to 100, respectively.
  • This disclosure provides a nonaqueous electrolyte that, when used in a nonaqueous electrolyte battery, can significantly suppress gas generation during high-temperature storage tests, a nonaqueous electrolyte battery, and a method for manufacturing a nonaqueous electrolyte battery. It also provides a compound that is suitable for use in the nonaqueous electrolyte, and a method for manufacturing the compound.

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Abstract

L'invention concerne : un électrolyte non aqueux contenant (I) un soluté, (II) un solvant organique non aqueux et (III) un composé représenté par la formule générale (1) décrite dans la description ; une batterie à électrolyte non aqueux comprenant au moins une électrode positive, une électrode négative et l'électrolyte non aqueux ; un procédé permettant de fabriquer la batterie à électrolyte non aqueux, le procédé comprenant une étape d'injection de l'électrolyte non aqueux ; un composé représenté par la formule générale (1) décrite dans la description ; et un procédé permettant de produire un composé représenté par la formule générale (1A) décrite dans la description.
PCT/JP2025/001504 2024-01-22 2025-01-20 Électrolyte non aqueux, batterie à électrolyte non aqueux, procédé permettant de fabriquer une batterie à électrolyte non aqueux, composé et procédé permettant de produire un composé Pending WO2025159037A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5210255A (en) * 1975-07-12 1977-01-26 Hoechst Ag Continuous production of 2*55dioxoo11oxaa22 phosphorane
JPH05194562A (ja) * 1991-08-09 1993-08-03 Sakai Chem Ind Co Ltd ホスフィニルカルボン酸誘導体の製造方法
JP2006160643A (ja) * 2004-12-06 2006-06-22 Nagase Chemtex Corp β，γ−不飽和ホスフィン酸エステルの製造方法
JP2009224258A (ja) * 2008-03-18 2009-10-01 Sony Corp 電解液および二次電池
JP2011049153A (ja) * 2009-07-28 2011-03-10 Mitsubishi Chemicals Corp 非水系電解液及びそれを用いた非水系電解液二次電池
KR101631513B1 (ko) * 2014-12-30 2016-06-17 강원대학교산학협력단 신규한 벤조[d][1,2]옥사포스포린 유도체 및 이의 제조방법

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5210255A (en) * 1975-07-12 1977-01-26 Hoechst Ag Continuous production of 2*55dioxoo11oxaa22 phosphorane
JPH05194562A (ja) * 1991-08-09 1993-08-03 Sakai Chem Ind Co Ltd ホスフィニルカルボン酸誘導体の製造方法
JP2006160643A (ja) * 2004-12-06 2006-06-22 Nagase Chemtex Corp β，γ−不飽和ホスフィン酸エステルの製造方法
JP2009224258A (ja) * 2008-03-18 2009-10-01 Sony Corp 電解液および二次電池
JP2011049153A (ja) * 2009-07-28 2011-03-10 Mitsubishi Chemicals Corp 非水系電解液及びそれを用いた非水系電解液二次電池
KR101631513B1 (ko) * 2014-12-30 2016-06-17 강원대학교산학협력단 신규한 벤조[d][1,2]옥사포스포린 유도체 및 이의 제조방법

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