Compound having oxazolidine structure, nonaqueous electrolyte containing said compound, and nonaqueous electrolyte battery containing said nonaqueous electrolyte

Abstract

Provided is a nonaqueous electrolyte capable of realizing excellent cycle characteristics compared to cases in which contained are compounds that are well known in the prior art.　The nonaqueous electrolyte contains (I) a solute, (II) a nonaqueous organic solvent, and (III) at least one compound selected from the group consisting of the compounds represented by formulae (1)-(8).

Description

Compound having an oxazolidine structure, non-aqueous electrolyte containing the same, and non-aqueous electrolyte battery containing the non-aqueous electrolyte

[0001] The present disclosure relates to an oxazolidine compound having a specific structure, a nonaqueous electrolyte containing the same, and a nonaqueous electrolyte battery including such a nonaqueous electrolyte.

[0002] In recent years, energy storage systems for applications requiring high energy density in information-related devices or communication devices, i.e., small devices such as personal computers, video cameras, digital still cameras, and mobile phones, as well as large devices requiring high power, such as electric vehicles, hybrid vehicles, auxiliary power sources for fuel cell vehicles, and power storage devices, have attracted attention. Non-aqueous electrolyte secondary batteries, such as lithium-ion batteries, lithium batteries, lithium-ion capacitors, and sodium-ion batteries, have been actively developed as candidates. Non-aqueous electrolyte secondary batteries are required to achieve high levels of battery characteristics, such as cycle characteristics, input / output characteristics, storage characteristics, continuous charging characteristics, and safety. Furthermore, in recent years, there has been an increasing demand for higher capacity automotive batteries to extend driving range.

[0003] Although many of these nonaqueous electrolyte secondary batteries have already been put to practical use, further improvements in terms of increasing capacity are desired. In particular, when alloy-based active materials, particularly active materials containing Si atoms, are used as negative electrode active materials, high battery capacity is expected, but it is known that battery performance deteriorates significantly with long-term use. Therefore, efforts have been made to increase capacity and improve durability in order to extend the driving range of, for example, automobiles. To date, optimization of various battery components, including the active materials of the positive and negative electrodes, has been investigated as a means of improving the high-temperature characteristics of nonaqueous electrolyte secondary batteries and their battery characteristics (cycling characteristics) during repeated charge and discharge. Nonaqueous electrolyte-related technologies are no exception, and various additives have been proposed to suppress deterioration due to electrolyte decomposition on the surfaces of active positive and negative electrodes.

[0004] Patent Document 1 reports an electrolyte solution for a nonaqueous electrolyte secondary battery containing a nitrogen-containing heterocyclic compound such as a pyrrolidine compound, an imidazolidine compound, or an oxazolidine compound, as a nonaqueous electrolyte solution having good battery characteristics, for example, high charge / discharge efficiency and capacity retention rate.

[0005] Also, Patent Document 2 reports a non-aqueous electrolyte containing an oxazolidine compound in a solvent containing a lactone compound having a 5- to 7-membered ring. Furthermore, Patent Document 3 reports that by adding a nitrogen-containing cyclic compound having an ester bond to a non-aqueous electrolyte, the capacity retention rates at 20°C and 60°C can be improved and the battery can be made flame-retardant.

[0006] Patent No. 5109213 Patent No. 4302366 Patent No. 5439345

[0007] The present inventors have investigated electrolytes containing oxazolidine compounds specifically disclosed in these patent documents (for example, 3-methyl-2-oxazolidone used in Example 2 of Patent Document 1 and Example 24 of Patent Document 2, 5,5-dimethyl-1,3-oxazolidin-2-one used in Example 1 of Patent Document 3, 3,5,5-trimethyloxazolidine-2,4-dione used in Example 4 of Patent Document 3, 5,5-dimethyl-3-ethyl-2,4-oxazolidinone used in Example 5 of Patent Document 3, etc.), and have found that there is room for improvement in terms of the discharge capacity retention rate after cycle testing (hereinafter also referred to as "cycle characteristics").

[0008] Therefore, the present disclosure has been made in consideration of the above circumstances, and aims to provide a non-aqueous electrolyte that contains an oxazolidine compound having a specific structure in the molecule and thereby can exhibit better cycle characteristics than when a known compound is contained, a non-aqueous electrolyte battery containing the same, and an oxazolidine compound having such a specific structure.

[0009] The present inventors have conducted extensive research into the above-mentioned problems and have found that when an oxazolidine compound having a specific structure in its molecule is incorporated into a non-aqueous electrolyte solution, better cycle characteristics are exhibited in a non-aqueous electrolyte battery than when a conventional known compound is incorporated, thereby completing the present invention.

[0010] That is, the present invention relates to the following inventions: 1. A non-aqueous electrolyte solution comprising: (I) a solute (hereinafter, sometimes referred to as "component (I)"), (II) a non-aqueous organic solvent (hereinafter, sometimes referred to as "component (II)"), and (III) at least one selected from the group consisting of a compound represented by the following general formula (1), a compound represented by the general formula (2), a compound represented by the general formula (3), a compound represented by the general formula (4), a compound represented by the general formula (5), a compound represented by the general formula (6), a compound represented by the general formula (7), and a compound represented by the general formula (8) (hereinafter, sometimes referred to as "component (III)").

[0011] In the general formula (1), m represents an integer of 0 or 1. a is a hydrogen atom or (M A+ ) a where M1 A+ represents a metal cation or an onium cation, A represents the valence of the cation, and a represents a number such that A×a=1. 1 is -S(=O)2R a , or -P(=O)(R b ) (R c ) represents. a , R b and R care each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M2 B+ ) b where M2 B+ represents a proton, a metal cation, or an onium cation, B represents the valence of the cation, and b represents a number such that B×b=1. b and R c may be taken together with each other to form a 5- or 6-membered ring together with the phosphorus atom. 2 and R 3 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 2 and R 3 may combine to form a carbonyl group.

[0012] In addition, (X) in the above general formula (1) m R 1 may be S(=O)F, S(=O)OLi, P(=O)(OCHC≡CH), S(=O)OCH, S(=O)NHS(=O)F, PF(=O)NLiS(=O)F, S(=O)CF, S(=O)CH, P(=O)(OCHCHCH) or P(=O)(-OCH-CHO-). From the viewpoint of cycle characteristics, preferably S(=O)2OLi, P(=O)F2, P(=O)(OCHC≡CH)2, S(=O)2OCH3, S(=O)2NHS(=O)2F or PF(=O)NLiS(=O)2F may be used, more preferably S(=O)2OLi, P(=O)F2, P(=O)(OCHC≡CH)2, S(=O)2NHS(=O)2F or PF(=O)NLiS(=O)2F may be used, and particularly preferably S(=O)2OLi, P(=O)F2, P(=O)(OCHC≡CH)2 or PF(=O)NLiS(=O)2F may be used. Furthermore, from the viewpoint of the effect of reducing the initial resistance (hereinafter sometimes referred to as "initial resistance characteristics") described later, preferably, S(=O)F, P(=O)F, S(=O)OLi, P(=O)(OCHC≡CH), S(=O)OCH, S(=O)NHS(=O)F, PF(=O)NLiS(=O)F or S(=O)CF may be used, and more preferably Preferably, S(=O)F, P(=O)F, S(=O)OLi, P(=O)(OCHC≡CH), S(=O)OCH, S(=O)NHS(=O)F or PF(=O)NLiS(=O)F, and particularly preferably S(=O)F, P(=O)F, S(=O)OLi or P(=O)(OCHC≡CH).

[0013] [In general formula (2), R 4 represents a halogen atom, -(O) x1 -S(=O)R d , -(O) y1 -P(=O)(R e ) (R f ), or -O - (M3 C+ ) c where M3 C+represents a proton, a metal cation or an onium cation, C represents the valence of the cation, c represents a number such that C×c=1, and x1 and y1 represent integers of 0 or 1. d , R e and R f are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M4 D+ ) d where M4 D+ represents a proton, a metal cation or an onium cation, D represents the valence of the cation, and d represents a number such that D×d=1. 5 and R 6 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 5 and R 6may combine to form a carbonyl group.

[0014] In addition, R in the above general formula (2) 4 may be OLi, F, P(=O)(OCHC≡CH)2, OS(=O)F, P(=O)F2, or S(=O)F. From the viewpoint of cycle characteristics, OLi, F, P(=O)(OCHC≡CH)2, or OS(=O)F may be preferred, OLi, F, or P(=O)(OCHC≡CH)2 may be more preferred, and OLi or F may be particularly preferred. From the viewpoint of initial resistance characteristics, OS(=O)2F, S(=O)2F, P(=O)F2, F, or OLi may be preferred, OS(=O)2F, S(=O)2F, P(=O)F2, or F may be preferred, and OS(=O)2F, S(=O)2F, or P(=O)F2 may be particularly preferred.

[0015] [In general formula (3), M b is a hydrogen atom or (M E+ ) e where M5 E+ represents a metal cation or an onium cation, E represents the valence of the cation, and e represents a number such that E×e=1. 7 and R 7' each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 ... a hydrocarbon group selected from an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), -S(=O)R g , or -P(=O)(R h ) (R i ) represents. g , R h and R i are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M6 F+ ) f where M6 F+represents a proton, a metal cation or an onium cation, F represents the valence of the cation, and f represents a number such that F×f=1. 8 and R 9 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 8 and R 9 may combine to form a carbonyl group.

[0016] In addition, Z in the above general formula (3) may be NLi-S(=O)2F, NLi-P(=O)F2, NLi-S(=O)2(OCHC≡CH), NLi-P(=O)(OCH5)2, N(CHC≡N)2, or NNa-S(=O)2F. From the viewpoint of cycle characteristics, Z may preferably be NLi-S(=O)2F, NLi-S(=O)2(OCHC≡CH), or NLi-P(=O)F2, and more preferably be NLi-S(=O)2F or NLi-S(=O)2(OCHC≡CH). Furthermore, from the viewpoint of initial resistance characteristics, NLi-S(=O)2F, NLi-P(=O)F2, NLi-S(=O)2(OCHC≡CH) or NLi-P(=O)(OCH5)2 may be preferably used, NLi-S(=O)2F, NLi-P(=O)F2 or NLi-S(=O)2(OCHC≡CH) may be more preferably used, and NLi-S(=O)2F or NLi-P(=O)F2 may be particularly preferably used.

[0017] [In general formula (4), R 10 , R 11 , R 12 and R 13each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 10 and R 11 or R 12 and R 13 may each independently and together form a carbonyl group.

[0018] In addition, the general formula (4) is R 10 ~R 13 may be a structure in which all of R 10 ~R 13 may be a structure in which all of R 10 ~R 13 may be a structure in which all of R 10 and R 11 is H and CH3 and R 12 and R 13 may be a structure in which R is H and CH. From the viewpoint of cycle characteristics, R 10 and R 11 is H and CH3 and R 12 and R 13 H and CH3, R 10 ~R 13 are all H or R 10 ~R 13 may be a structure in which all of R 10 and R 11 is H and CH3 and R 12 and R 13 is H and CH3 or R 10 ~R 13 may be a structure in which all of R are H, and particularly preferred 10 and R 11is H and CH3 and R 12 and R 13 may be H and CH3. From the viewpoint of initial resistance characteristics, it is preferable that R 10 ~R 13 a structure in which all are F; 10 ~R 13 or a structure in which R 10 and R 11 is H and CH3 and R 12 and R 13 may be H and CH3.

[0019] In the general formula (5), n represents an integer of 0 or 1. c is a hydrogen atom or (M G+ ) g where M7 G+ represents a metal cation or an onium cation, G represents the valence of the cation, and g represents a number such that G×g=1. 14 is -S(=O)2R j , or -P(=O)(R k ) (R l ), where R j , R k and R l are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M8 H+) h where M8 H+ represents a proton, a metal cation or an onium cation, H represents the valence of the cation, and h represents a number such that H×h=1. 15 and R 16 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 15 and R 16 may combine to form a carbonyl group.

[0020] In addition, (Y) in the above general formula (5) n R 14 may be S(═O)2OLi, S(═O)2F, P(═O)F2, or P(═O)(OCH3)2. From the viewpoint of cycle characteristics and initial resistance characteristics, S(═O)2OLi, S(═O)2F, or P(═O)F2 may be preferred, and S(═O)2OLi or S(═O)2F may be more preferred.

[0021] [In general formula (6), R 17 represents a halogen atom, -(O) x2 -S(=O)R m , -(O) y2 -P(=O)(R n ) (R o ), or -O - (M9 I+ ) i where M9 I+represents a proton, a metal cation, or an onium cation, I represents the valence of the cation, and i represents a number such that I×i=1. x2 and y2 represent integers of 0 or 1. R m , R n and R o are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M 10 J+ ) j where M 10 J+ represents a proton, a metal cation or an onium cation, J represents the valence of the cation, and j represents a number such that J×j=1. 18 and R 19 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group).18 and R 19 may combine to form a carbonyl group.

[0022] In addition, R in the above general formula (6) 17 may be OP(=O)F, S(=O)(OCHC≡CH), OLi, or F. From the viewpoint of cycle characteristics and initial resistance characteristics, OP(=O)F, S(=O)(OCHC≡CH), or OLi may be preferred, and OP(=O)F or S(=O)(OCHC≡CH) may be more preferred.

[0023] [In general formula (7), M d is a hydrogen atom or (M 11 K+ ) k where M 11 K+ represents a metal cation or an onium cation, K represents the valence of the cation, and k represents a number such that K×k=1. 20 and R 20’ are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 ... a hydrocarbon group selected from an aryloxy group represented by the formula (I), a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), -S(=O)R p , or -P(=O)(R q ) (R r ) represents. p , R q and R rare each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M 12 L+ ) l where M 12 L+ represents a proton, a metal cation or an onium cation, L represents the valence of the cation, and l represents a number such that L×l=1. 21 and R 22 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 21 and R 22 may combine to form a carbonyl group.

[0024] Z' in the general formula (7) may be NLi-S(=O)F, NLi-P(=O)(OCHCF) or NH-P(=O)F. From the viewpoint of cycle characteristics, NLi-P(=O)(OCHCF) is preferred. From the viewpoint of initial resistance characteristics, NLi-S(=O)F or NH-P(=O)F is preferred, and NLi-S(=O)F is more preferred.

[0025] [In general formula (8), R 23 , R 24 , R 25 and R 26 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 23 and R 24 , or R 25 and R 26 may each independently and together form a carbonyl group.

[0026] In addition, in the above general formula (8), R 23 and R 24 is H and CH3 and R 25 and R 26 may be a structure in which R is H and CH 23 ~R 26 In view of cycle characteristics, it is preferable that R 23 and R 24 is H and CH3 and R 25 and R 26 may be H and CH3. From the viewpoint of initial resistance characteristics, it is preferable that R 23 ~R26 may be a structure in which all of the

[0027] 2. The non-aqueous electrolyte solution according to item 1, wherein the concentration of (III) is 0.009 to 11.5 mass % relative to the total amount of the non-aqueous electrolyte solution.

[0028] 3. The non-aqueous electrolyte solution according to any one of items 1 to 2 above, wherein (III) is at least one selected from the group consisting of compounds represented by general formula (1), compounds represented by general formula (2), compounds represented by general formula (3), compounds represented by general formula (4), compounds represented by general formula (5), compounds represented by general formula (6), and compounds represented by general formula (7). 4. The non-aqueous electrolyte solution according to any one of items 1 to 3 above, wherein (III) is at least one selected from the group consisting of compounds represented by general formula (1), compounds represented by general formula (2), compounds represented by general formula (3), and compounds represented by general formula (4). 5. The non-aqueous electrolyte solution according to any one of items 1 to 4 above, wherein the compound represented by general formula (1) is at least one selected from the following compounds:

[0029]

[0030]

[0031] 6. The nonaqueous electrolyte solution according to any one of items 1 to 4 above, wherein the compound represented by general formula (2) is at least one selected from the following compounds:

[0032]

[0033]

[0034] 7. The non-aqueous electrolyte solution according to any one of items 1 to 4 above, wherein the compound represented by general formula (3) is at least one selected from the following compounds:

[0035]

[0036] 8. The non-aqueous electrolyte solution according to any one of items 1 to 4 above, wherein the compound represented by general formula (4) is at least one selected from the following compounds:

[0037] 9. The nonaqueous electrolyte solution according to any one of items 1 to 3 above, wherein the compound represented by general formula (5) is at least one selected from the following compounds:

[0038]

[0039] 4. The non-aqueous electrolyte solution according to any one of items 1 to 3 above, wherein the compound represented by general formula (6) is at least one selected from the following compounds:

[0040]

[0041] 11. The nonaqueous electrolyte solution according to any one of items 1 to 3 above, wherein the compound represented by general formula (7) is at least one selected from the following compounds:

[0042]

[0043] 12. The nonaqueous electrolyte solution according to the above 1 or 2, wherein the compound represented by the general formula (8) is at least one selected from the following compounds:

[0044] 13. The nonaqueous electrolyte according to any one of items 1 to 12 above, wherein (I) is at least one selected from the group consisting of LiPF6, LiBF4, LiSbF6, LiAsF6, LiClO4, LiN(SO2F)2 (hereinafter sometimes referred to as "FSI"), LiAlO2, LiAlCl4, LiCl, and LiI, or at least one selected from the group consisting of NaPF6, NaBF4, NaSbF6, NaAsF6, NaClO4, NaN(SO2F)2, NaAlO2, NaAlCl4, NaCl, and NaI. 14. The nonaqueous electrolyte according to item 1 or 2 above, wherein (II) includes at least one selected from the group consisting of cyclic esters, chain esters, cyclic ethers, chain ethers, sulfone compounds, sulfoxide compounds, and ionic liquids. 15. 16. The non-aqueous electrolyte solution according to the above 14, wherein the cyclic ester comprises a cyclic carbonate. 16. The non-aqueous electrolyte solution according to the above 15, wherein the cyclic carbonate comprises at least one selected from the group consisting of ethylene carbonate and propylene carbonate.

[0045] 17. The non-aqueous electrolyte according to the above item 14, wherein the chain ester comprises a chain carbonate. 18. The non-aqueous electrolyte according to the above item 17, wherein the chain carbonate comprises at least one selected from the group consisting of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, and methyl propyl carbonate. 19. Further, cyclohexylbenzene, cyclohexylfluorobenzene, biphenyl, 2-fluorobiphenyl, t-butylbenzene, t-amylbenzene, 2-fluorotoluene, fluorobenzene, vinylene carbonate (hereinafter sometimes referred to as "VC"), vinylene carbonate oligomer (having a number average molecular weight of 170 to 5000 in terms of polystyrene), vinylethylene carbonate, difluoroanisole, fluoroethylene carbonate (hereinafter sometimes referred to as "FEC"), 1,6-diisocyanatohexane, ethynylethylene carbonate, trans-difluoroethylene carbonate, methyl propargyl carbonate, ethyl propargyl carbonate, dipropargyl carbonate, maleic anhydride, succinic anhydride, 1,3-propane sultone, 1,3-propane sultone, methylpropargyl carbonate, ethylprop ... Lopensultone, 1,4-butanesultone, dimethylvinylene carbonate, 1,3,2-dioxathiolane-2,2-dioxide (hereinafter sometimes referred to as "DTD"), 4-propyl-1,3,2-dioxathiolane-2,2-dioxide, methylenemethane disulfonate, dimethylenemethane disulfonate, trimethylenemethane disulfonate, methyl methanesulfonate, methanesulfonyl fluoride, ethenesulfonyl fluoride, phenyl difluorophosphate, 1,2-ethanedisulfonic anhydride, tris(trimethylsilyl)borate, succinonitrile, (ethoxy)pentafluorocyclotriphosphazene, tetrafluoro(picolinato)phosphate, difluoro(picolinato)borate, 1,3-dimethyl-1,3-divinyl-1,3-di(1,1,1,3,3,3-hexafluoroisopropyl)disiloxane, lithium difluorophosphate (hereinafter may be referred to as "DFP"), sodium difluorophosphate, lithium fluorosulfate (hereinafter may be referred to as "FS"), sodium fluorosulfate, lithium trifluoromethanesulfonate, sodium trifluoromethanesulfonate, lithium nonafluorobutanesulfonate, sodium nonafluorobutanesulfonate, lithium difluorobis(oxalato)phosphate (hereinafter may be referred to as "DFBOP"), sodium difluorobis(oxalato)phosphate, lithium difluorooxalatoborate (hereinafter may be referred to as "DFOB"),

[0046] Sodium difluorooxalatoborate, lithium bis(oxalato)borate (hereinafter sometimes referred to as "BOB"), sodium bis(oxalato)borate, lithium tetrafluorooxalatophosphate (hereinafter sometimes referred to as "TFOP"), sodium tetrafluorooxalatophosphate, lithium tris(oxalato)phosphate, sodium tris(oxalato)phosphate, lithium difluoro(malonato)borate, sodium difluoro(malonato)borate, lithium tetrafluoro(malonato)phosphate, tetrafluoro(malonato) Sodium phosphate, lithium monofluorophosphate, sodium monofluorophosphate, lithium bis(difluorophosphoryl)imide, sodium bis(difluorophosphoryl)imide, lithium (difluorophosphoryl)(fluorosulfonyl)imide (hereinafter sometimes referred to as "DFPFSI"), sodium (difluorophosphoryl)(fluorosulfonyl)imide, lithium bis(trifluoromethanesulfonyl)imide, sodium bis(trifluoromethanesulfonyl)imide, lithium bis(pentafluoroethanesulfonyl)imide 19. The non-aqueous electrolyte solution according to any one of items 1 to 18, further comprising at least one selected from the group consisting of lithium, bis(pentafluoroethanesulfonyl)imide sodium, (trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)imide lithium, (trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)imide sodium, (trifluoromethanesulfonyl)(fluorosulfonyl)imide lithium, (trifluoromethanesulfonyl)(fluorosulfonyl)imide sodium, (pentafluoroethanesulfonyl)(fluorosulfonyl)imide lithium, (pentafluoroethanesulfonyl)(fluorosulfonyl)imide sodium, tris(trifluoromethanesulfonyl)methide lithium, tris(trifluoromethanesulfonyl)methide sodium, lithium acrylate, sodium acrylate, lithium methacrylate, sodium methacrylate, lithium methyl sulfate, sodium methyl sulfate, lithium ethyl sulfate, sodium ethyl sulfate, lithium nitrate, lithium nitrite, sodium nitrite, and sodium nitrite.20. The nonaqueous electrolyte solution according to any one of items 1 to 19 above, further comprising a compound represented by the following general formula (9):

[0047] [In general formula (9), R 27 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, and an oxygen atom may be contained between any carbon atom-carbon atom bond in the alkyl group. Any hydrogen atom in the alkyl group may be substituted with a fluorine atom.] 21. The compound represented by general formula (9) is the following compound 1-1 (hereinafter, sometimes referred to as "TDUTO") and 1-2,

[0048] 22. The nonaqueous electrolyte solution according to any one of items 1 to 21 above, further comprising a compound represented by the following general formula (10): [In general formula (10), R 28 ~R 31 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, or an aryl group. X represents an oxygen atom, a sulfur atom, or an SO group. 23. The nonaqueous electrolyte solution according to the above 22, wherein the compound of formula (10) is a compound represented by the following formula: 24. A nonaqueous electrolyte battery comprising at least a positive electrode, a negative electrode, a separator, and the nonaqueous electrolyte solution according to any one of items 1 to 23 above. 25. A compound represented by any one of the following general formulas (1) to (8):

[0049] In the general formula (1), m represents an integer of 0 or 1. a is a hydrogen atom or (M A+ ) a where M1 A+ represents a metal cation or an onium cation, A represents the valence of the cation, and a represents a number such that A×a=1. 1 is -S(=O)2R a , or -P(=O)(R b ) (R c ) represents. a, R b and R c are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M2 B+ ) b where M2 B+ represents a proton, a metal cation, or an onium cation, B represents the valence of the cation, and b represents a number such that B×b=1. b and R c may be taken together with each other to form a 5- or 6-membered ring together with the phosphorus atom. 2 and R 3 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 2 and R 3 may combine to form a carbonyl group.

[0050] [In general formula (2), R 4 represents a halogen atom, -(O) x1 -S(=O)R d , -(O) y1 -P(=O)(R e ) (R f ), or -O - (M3 C+ ) c where M3 C+ represents a proton, a metal cation or an onium cation, C represents the valence of the cation, c represents a number such that C×c=1, and x1 and y1 represent integers of 0 or 1. d , R e and R f are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M4 D+ ) d where M4 D+ represents a proton, a metal cation or an onium cation, D represents the valence of the cation, and d represents a number such that D×d=1. 5 and R 6each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 5 and R 6 may combine to form a carbonyl group.

[0051] [In general formula (3), M b is a hydrogen atom or (M E+ ) e where M5 E+ represents a metal cation or an onium cation, E represents the valence of the cation, and e represents a number such that E×e=1. 7 and R 7 ' each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 ... a hydrocarbon group selected from an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), -S(=O)R g , or -P(=O)(R h ) (Ri ) represents. g , R h and R i are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M6 F+ ) f where M6 F+ represents a proton, a metal cation or an onium cation, F represents the valence of the cation, and f represents a number such that F×f=1. 8 and R 9 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 8 and R 9 may combine to form a carbonyl group.

[0052] [In general formula (4), R 10 , R 11 , R 12 and R 13 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 10 and R 11 or R 12 and R 13 may each independently and together form a carbonyl group.

[0053] In the general formula (5), n represents an integer of 0 or 1. c is a hydrogen atom or (M G+ ) g where M7 G+ represents a metal cation or an onium cation, G represents the valence of the cation, and g represents a number such that G×g=1. 14 is -S(=O)2R j , or -P(=O)(R k ) (R l ), where R j , R k and R lare each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M8 H+ ) h where M8 H+ represents a proton, a metal cation or an onium cation, H represents the valence of the cation, and h represents a number such that H×h=1. 15 and R 16 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 15 and R 16 may combine to form a carbonyl group.

[0054] [In general formula (6), R 17 represents a halogen atom, -(O) x2 -S(=O)Rm , -(O) y2 -P(=O)(R n ) (R o ), or -O - (M9 I+ ) i where M9 I+ represents a proton, a metal cation, or an onium cation, I represents the valence of the cation, and i represents a number such that I×i=1. x2 and y2 represent integers of 0 or 1. R m , R n and R o are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M 10 J+ ) j where M 10 J+ represents a proton, a metal cation or an onium cation, J represents the valence of the cation, and j represents a number such that J×j=1. 18 and R 19each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 18 and R 19 may combine to form a carbonyl group.

[0055] [In general formula (7), M d is a hydrogen atom or (M 11 K+ ) k where M 11 K+ represents a metal cation or an onium cation, K represents the valence of the cation, and k represents a number such that K×k=1. 20 and R 20’ are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 ... a hydrocarbon group selected from an aryloxy group represented by the formula (I), a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), -S(=O)R p, or -P(=O)(R q ) (R r ) represents. p , R q and R r are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon atoms in the hydrocarbon group), or -O - (M 12 L+ ) l where M 12 L+ represents a proton, a metal cation or an onium cation, L represents the valence of the cation, and l represents a number such that L×l=1. 21 and R 22 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 21 and R 22may combine to form a carbonyl group.

[0056] [In general formula (8), R 23 , R 24 , R 25 and R 26 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (some or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon groups in the hydrocarbon group). 23 and R 24 , or R 25 and R 26 may each independently form a carbonyl group together.] 26. The compound according to the above 25, wherein the compound represented by the general formula (1) is selected from the following compounds:

[0057]

[0058] 27. The compound according to the above 25, wherein the compound represented by the general formula (2) is selected from the following compounds:

[0059]

[0060]

[0061]

[0062]

[0063] 28. The compound according to the above 25, wherein the compound represented by the general formula (3) is selected from the following compounds:

[0064]

[0065]

[0066] 29. The compound according to the above 25, wherein the compound represented by the general formula (4) is selected from the following compounds:

[0067]

[0068] 30. The compound according to the above 25, wherein the compound represented by the general formula (5) is selected from the following compounds:

[0069]

[0070] 31. The compound according to the above 25, wherein the compound represented by the general formula (6) is selected from the following compounds:

[0071]

[0072] 32. The compound according to the above 25, wherein the compound represented by the general formula (7) is selected from the following compounds:

[0073] 33. The compound according to the above 25, wherein the compound represented by the general formula (8) is selected from the following compounds:

[0074]

[0075] According to the present disclosure, it is possible to provide a non-aqueous electrolyte that contains an oxazolidine compound having a specific structure in its molecule, thereby exhibiting better cycle characteristics than when a known compound is contained, a non-aqueous electrolyte battery containing the same, and an oxazolidine compound having such a specific structure.

[0076] The composition of the non-aqueous electrolyte according to the present disclosure will be described in detail below. Regarding component (I) (solute), the solute used in the non-aqueous electrolyte according to the present disclosure can be any of various solutes that have been used in the field of non-aqueous electrolytes, without any particular limitations. As such a solute, an ionic salt consisting of any pair of cation and anion is preferred. As long as it exists in an ionic state as a cation and an anion in a non-aqueous organic solvent, various solutes can be used without any particular limitations.

[0077] Specific examples of such solutes include at least one selected from the group consisting of LiPF, LiBF, LiSbF, LiAsF, LiClO, LiN(SOF), LiAlO, LiAlCl, LiCl, and LiI, and at least one selected from the group consisting of NaPF, NaBF, NaSbF, NaAsF, NaClO, NaN(SOF), NaAlO, NaAlCl, NaCl, and NaI.

[0078] In particular, in consideration of the energy density, output characteristics, life, etc. of the nonaqueous electrolyte battery, it is preferable that the cation is at least one selected from the group consisting of lithium, sodium, potassium, magnesium, and quaternary ammonium, and the anion is at least one selected from the group consisting of hexafluorophosphate anion, tetrafluoroborate anion, and bis(fluorosulfonyl)imide anion. In the present disclosure, one type of solute may be used alone, or two or more types may be used in any combination and ratio depending on the application.

[0079] The solute concentration in the present disclosure may be, for example, 0.5 mol / L or more, preferably 0.7 mol / L or more, and more preferably 0.9 mol / L or more, relative to the total amount of the nonaqueous electrolyte. The upper limit may be 5 mol / L or less, preferably 4 mol / L or less, and more preferably 2 mol / L or less. A concentration of 0.5 mol / L or more is preferable because the ionic conductivity is less likely to decrease, and the cycle characteristics and output characteristics of the nonaqueous electrolyte battery are less likely to decrease. On the other hand, a concentration of 5 mol / L or less is preferable because the viscosity of the nonaqueous electrolyte is less likely to increase, and the ionic conductivity is less likely to decrease. When two or more solutes are used, the total concentration of the solutes is preferably within the above-mentioned range. The solution temperature when dissolving the solute in the nonaqueous organic solvent described below is not particularly limited, but is preferably, for example, −20 to 80°C, and more preferably 0 to 60°C.

[0080] Regarding component (II) (non-aqueous organic solvent), the non-aqueous organic solvent used in the non-aqueous electrolyte solution of the present disclosure is not particularly limited as long as it can dissolve the above-mentioned component (I) and the additive (III) described below, and any non-aqueous organic solvent can be used. The non-aqueous organic solvent is preferably at least one selected from the group consisting of cyclic esters, linear esters, cyclic ethers, linear 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, linear esters, cyclic ethers, linear ethers, sulfone compounds, sulfoxide compounds, and ionic liquids. Note that cyclic carbonates are a sub-concept of cyclic esters, and linear carbonates are a sub-concept of linear esters.

[0081] Specific examples of the non-aqueous organic solvent used in the present disclosure include ethyl methyl carbonate (hereinafter also referred to as "EMC"), dimethyl carbonate (hereinafter also referred to as "DMC"), diethyl carbonate (hereinafter also referred to as "DEC"), 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, bis(2,2,2-trifluoroethyl)carbonate, 1,1,1,3,3,3-hexafluoro-1-propyl methyl carbonate, 1,1,1,3,3,3-hexafluoro-1-propyl ethyl carbonate, 1,1,1,3,3,3-hexafluoro-1-propyl propyl carbonate, bis( 1,1,1,3,3,3-hexafluoro-1-propyl) carbonate, ethylene carbonate (hereinafter also referred to as "EC"), propylene carbonate (hereinafter also referred to as "PC"), butylene carbonate, methyl acetate, ethyl acetate, methyl propionate, ethyl propionate, methyl 2-fluoropropionate, ethyl 2-fluoropropionate, diethyl ether, dibutyl ether, diisopropyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, furan, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, N,N-dimethylformamide, acetonitrile, propionitrile, dimethyl sulfoxide, sulfolane, γ-butyrolactone, and γ-valerolactone, and the like may be included, and at least one of the above specific examples may be included.

[0082] The nonaqueous organic solvent preferably contains at least one selected from the group consisting of cyclic esters and chain esters, which provides excellent input / output characteristics at low temperatures, and the nonaqueous organic solvent preferably contains at least one selected from the group consisting of cyclic carbonates and chain carbonates, which provides excellent cycle characteristics at high temperatures.

[0083] The nonaqueous organic solvent preferably contains a cyclic ester, and the cyclic ester preferably contains a cyclic carbonate. Specific examples of the cyclic carbonate include EC, PC, and butylene carbonate, and among these, it is preferable to contain at least one selected from the group consisting of EC and PC.

[0084] It is also preferable that the nonaqueous organic solvent contains a chain ester, and that the chain ester contains a chain carbonate. Specific examples of the chain carbonate include EMC, DMC, DEC, methyl propyl carbonate, ethyl propyl carbonate, 2,2,2-trifluoroethyl methyl carbonate, 2,2,2-trifluoroethyl ethyl carbonate, 1,1,1,3,3,3-hexafluoro-1-propyl methyl carbonate, and 1,1,1,3,3,3-hexafluoro-1-propyl ethyl carbonate. Of these, it is preferable that the solvent contains at least one selected from the group consisting of EMC, DMC, DEC, and methyl propyl carbonate. Specific examples of the chain ester include methyl acetate, ethyl acetate, methyl propionate, ethyl propionate, methyl 2-fluoropropionate, ethyl 2-fluoropropionate, and methyl 3,3,3-trifluoropropionate. The nonaqueous organic solvent of the present disclosure may be used alone, or two or more types may be used in any combination and ratio depending on the application. Among these, from the viewpoints of electrochemical stability against oxidation-reduction and chemical stability related to heat and reactions with the solute, it is preferable to include at least one selected from the group consisting of PC, EC, DEC, DMC, and EMC. The concentration of the nonaqueous organic solvent of the present disclosure is not particularly limited as long as it functions as a nonaqueous organic solvent, but may be, for example, 40 to 99% by mass, preferably 50 to 95% by mass, and particularly preferably 70 to 93% by mass relative to the total amount (100% by mass) of the nonaqueous electrolyte.

[0085] Regarding Component (III): The additives used in the nonaqueous electrolyte solution of the present disclosure are the eight types of compounds described above. Here, the meanings of the functional groups described in each formula are as follows. The halogen atom is selected from halogen atoms such as fluorine, chlorine, and bromine. Preferably, the halogen atom is a fluorine atom. The alkyl group having 1 to 10 carbon atoms may be linear or branched, and preferably has 1 to 10 carbon atoms, and preferably 1 to 5 carbon atoms. Examples of such alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl, and n-decyl groups. Examples of the alkoxy group having 1 to 10 carbon atoms include alkoxy groups corresponding to the above alkyl groups.

[0086] Examples of alkenyl groups having 2 to 10 carbon atoms include linear or branched alkenyl groups, with alkenyl groups having 2 to 5 carbon atoms being preferred. The alkenyl group may also have two or more unsaturated bonds. Suitable examples of such alkenyl groups include vinyl groups, 1-propenyl groups, 2-propenyl groups, 1-methylvinyl groups, 1-butenyl groups, 2-butenyl groups, 3-butenyl groups, 1-methylpropenyl groups, 1-pentenyl groups, and 1,3-butadienyl groups. Examples of alkenyloxy groups having 2 to 10 carbon atoms include alkenyloxy groups corresponding to the above alkenyl groups. Examples of alkynyl groups having 2 to 10 carbon atoms include linear or branched alkynyl groups, with alkynyl groups having 2 to 5 carbon atoms being preferred. The alkynyl group may also have two or more unsaturated bonds. Suitable examples of such alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methylethynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpropynyl, 1,1-dimethyl-2-propynyl, 1-pentynyl, and 1,3-butadienyl. Examples of the alkynyloxy group having 2 to 10 carbon atoms include alkynyloxy groups corresponding to the above alkynyl groups.

[0087] As the cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 5 carbon atoms is preferred, and suitable examples of such cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The cycloalkyl group also includes those having a linking group such as a methylene group, and suitable examples include a cyclohexylmethyl group. As the cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkoxy group corresponding to the cycloalkyl group is preferred. As the cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 5 carbon atoms is preferred, and suitable examples of such cycloalkenyl groups include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group. The cycloalkenyl group also includes those having a linking group such as a methylene group, and suitable examples include a cyclohexenylmethyl group. Preferred examples of cycloalkenyloxy groups having 3 to 8 carbon atoms include cycloalkenyloxy groups corresponding to the above-mentioned cycloalkenyl groups. Preferred examples of aryl groups having 6 to 10 carbon atoms include phenyl and naphthalene groups. The above-mentioned aryl groups also include those having a linking group such as a methylene group, and preferred examples include a benzyl group. Preferred examples of aryloxy groups having 6 to 10 carbon atoms include a phenoxy and naphthoxy group. Preferred examples of heteroaryl groups having 6 to 10 carbon atoms include an aryl group containing a heteroatom such as an oxygen atom, sulfur atom, or nitrogen atom. Preferred examples of such heteroaryl groups include a furyl group, a thiophenyl group, a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, a thioxazole group, a pyridyl group, a pyridazine group, a pyrimidine group, a pyrazine group, a triazine group, an indole group, a purine group, and a quinolyl group. Suitable examples of the heteroaryloxy group having 6 to 10 carbon atoms include heteroaryloxy groups corresponding to the above heteroaryl groups.

[0088] The hydrogen atoms of the hydrocarbon group may be optionally substituted with halogen atoms, cyano groups, isocyano groups, or the like. Furthermore, a carbonyl group, oxygen atom, sulfur atom, nitrogen atom, or a combination thereof may be present between any carbon-carbon atoms of the hydrocarbon group. For example, when the hydrocarbon group is an alkyl group, suitable examples include a trifluoromethyl group and a 1,1,1-trifluoroethyl group. Suitable examples of metal cations include alkali metal cations such as lithium ion, sodium ion, and potassium ion, and alkaline earth metal cations such as magnesium ion and calcium ion. Suitable examples of onium cations include trialkylammonium ions, tetraalkylammonium ions, tetraalkylphosphonium ions, imidazolium ions, ammonium ions having a spiro skeleton, and nitronium cations. Examples of compounds represented by general formula (1) include the following compounds:

[0089]

[0090] Examples of the compound represented by formula (2) include the following compounds.

[0091]

[0092]

[0093]

[0094] Examples of the compound represented by formula (3) include the following compounds.

[0095]

[0096] Examples of the compound represented by formula (4) include the following compounds.

[0097] Examples of the compound represented by formula (5) include the following compounds.

[0098]

[0099] Examples of the compound represented by formula (6) include the following compounds.

[0100]

[0101] Examples of the compound represented by formula (7) include the following compounds.

[0102]

[0103] Examples of the compound represented by formula (8) include the following compounds.

[0104]

[0105] The compounds represented by general formulas (1) to (8), which are component (III) in the present disclosure, can be synthesized using known synthesis reactions once their chemical structures are understood. In the present disclosure, the synthesis reactions will be specifically clarified through synthesis examples, as described below. The compounds represented by general formulas (1) to (8) may be used alone or in any combination and ratio of two or more. Regarding component (III), at least one selected from the group consisting of compounds represented by general formulas (1) to (4) is preferred from the viewpoints of (i) improving the discharge capacity retention rate after a cycle test, (ii) improving (suppressing) the initial resistance, (iii) achieving a balanced improvement in the discharge capacity retention rate and the initial resistance after a cycle test, or (iv) improving (suppressing) the amount of gas generation during a cycle test. Furthermore, in lithium-ion batteries in which the cation is primarily lithium, from the viewpoint of (i) or (ii) above, at least one selected from the group consisting of compounds represented by general formulas (1) to (7) is preferred, and at least one selected from the group consisting of compounds represented by general formulas (1) to (4) is particularly preferred. Furthermore, in sodium-ion batteries in which the cation is primarily sodium, from the viewpoint of (i) above, at least one selected from the group consisting of compounds represented by general formulas (1) to (4) and (8) is preferred, and at least one selected from the group consisting of compounds represented by general formulas (1) to (4) is particularly preferred. The component (III) of the present disclosure may be, for example, 0.009 to 11.5 mass%, preferably 0.05 to 8.5 mass%, more preferably 0.09 to 5 mass%, relative to the total amount of the nonaqueous electrolyte. Within this range, the discharge capacity retention rate characteristics in cycle tests when used as a nonaqueous electrolyte battery are likely to be improved.

[0106] <Regarding Other Additives> The nonaqueous electrolyte solution of the present disclosure is constituted by the above-described components (I), (II), and (III) as basic constituents. However, other additives commonly used in this technical field (hereinafter also referred to as "other additives") may be added to the nonaqueous electrolyte solution of the present disclosure in any ratio, as long as the gist of the present disclosure is not impaired. Examples of such other additives include cyclohexylbenzene, cyclohexylfluorobenzene, biphenyl, 2-fluorobiphenyl, t-butylbenzene, t-amylbenzene, 2-fluorotoluene, fluorobenzene, vinylene carbonate, vinylene carbonate oligomers (having a number average molecular weight of 170 to 5,000 in terms of polystyrene), vinylethylene carbonate, difluoroanisole, fluoroethylene carbonate, 1,6-diisocyanatohexane, ethynylethylene carbonate, trans-difluoroethylene carbonate, methyl propargyl carbonate, ethyl propargyl carbonate, dipropargyl carbonate, maleic anhydride, succinic anhydride, 1,3-propane sultone, 1,3-propene sultone, and 1,4-butane. Examples of suitable fluoropolymers include methyl methyl ether, methyl vinylene carbonate, 1,3,2-dioxathiolane-2,2-dioxide, 4-propyl-1,3,2-dioxathiolane-2,2-dioxide, methylenemethane disulfonate, dimethylmethane disulfonate, trimethylenemethane disulfonate, methyl methanesulfonate, methanesulfonyl fluoride, ethenesulfonyl fluoride, phenyl difluorophosphate, 1,2-ethanedisulfonic anhydride, tris(trimethylsilyl)borate, succinonitrile, (ethoxy)pentafluorocyclotriphosphazene, tetrafluoro(picolinato)phosphate, difluoro(picolinato)borate, and 1,3-dimethyl-1,3-divinyl-1,3-di(1,1,1,3,3,3-hexafluoroisopropyl)disiloxane.

[0107] Other additives include, for example, lithium difluorophosphate, sodium difluorophosphate, lithium fluorosulfate, sodium fluorosulfate, lithium trifluoromethanesulfonate, sodium trifluoromethanesulfonate, lithium nonafluorobutanesulfonate, sodium nonafluorobutanesulfonate, lithium difluorobis(oxalato)phosphate, sodium difluorobis(oxalato)phosphate, lithium difluorooxalatoborate, sodium difluorooxalatoborate, lithium bis(oxalato)borate, sodium bis(oxalato)borate, lithium tetrafluorooxalatophosphate, sodium tetrafluorooxalatophosphate, lithium tris(oxalato)phosphate, sodium tris(oxalato)phosphate, lithium difluoro(malonato)borate, sodium difluoro(malonato)borate, lithium tetrafluoro(malonato)phosphate, sodium tetrafluoro(malonato)phosphate, lithium monofluorophosphate, sodium monofluorophosphate, lithium bis(difluorophosphoryl)imide, sodium bis(difluorophosphoryl)imide Thorium, (difluorophosphoryl)(fluorosulfonyl)imide lithium, (difluorophosphoryl)(fluorosulfonyl)imide sodium, bis(trifluoromethanesulfonyl)imide lithium, bis(trifluoromethanesulfonyl)imide sodium, bis(pentafluoroethanesulfonyl)imide lithium, bis(pentafluoroethanesulfonyl)imide sodium, (trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)imide lithium, (trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)imide sodium, (trifluoromethanesulfonyl)(fluorosulfonyl)imide lithium, (trifluoromethanesulfonyl)(fluorosulfonyl)imide sodium, (pentafluoroethanesulfonyl)(fluorosulfonyl)imide lithium, (pentafluoroethanesulfonyl)(fluorosulfonyl)imide sodium, tris(trifluoromethanesulfonyl)methide lithium, tris(trifluoromethanesulfonyl)methide sodium, lithium acrylate, sodium acrylate, lithium methacrylate,Examples of such additives include carboxylates such as sodium methacrylate, sulfates such as lithium methyl sulfate, sodium methyl sulfate, lithium ethyl sulfate, and sodium ethyl sulfate, lithium nitrate, lithium nitrite, sodium nitrite, and sodium nitrite. In the present disclosure, the concentration of the other additives may be, for example, 0.01% by mass to 10% by mass relative to the total amount of the non-aqueous electrolyte. Furthermore, the non-aqueous electrolyte of the present disclosure may further contain a compound represented by the following general formula (9) in order to improve cycle capacity retention and gas generation during cycle testing:

[0108] In general formula (9), R 27 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms, and an oxygen atom may be present between any carbon atom-carbon atom bond in the alkyl group. Any hydrogen atom in the alkyl group may be substituted with a fluorine atom. The range of alkyl groups includes the range of alkyl groups having 1 to 10 carbon atoms described above, as well as alkyl groups having up to 12 carbon atoms. Suitable examples of such compounds include Compounds 1-1 and 1-2 below. All compounds represented by general formula (9) can be easily manufactured or prepared by those skilled in the art using known preparation methods. Specifically, compounds represented by general formula (9) can be prepared by methods disclosed in documents such as Can. J. Chem., 79, 1040-1048 (2001).

[0109] The concentration of such a compound may be, for example, 0.01 to 10 mass %, and preferably 0.1 to 5 mass %, relative to the total amount of the nonaqueous electrolyte solution of the present disclosure. In addition, the nonaqueous electrolyte solution of the present disclosure may further contain a compound represented by the following general formula (10) in order to improve the cycle capacity retention rate and gas generation during cycle testing. In general formula (10), R 28 ~R 31each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, or an aryl group. X represents an oxygen atom, a sulfur atom, or an SO group. From the viewpoint of initial resistance, the compound of formula (10) is preferably a compound represented by the following formula: Any compound of general formula (10) can be easily manufactured or prepared by a person skilled in the art using known preparation methods. For example, the compound represented by the above formula is a known compound and is commercially available, for example, from Tokyo Chemical Industry Co., Ltd. The concentration of such a compound may be, for example, 0.01 to 10 mass% relative to the total amount of the nonaqueous electrolyte solution of the present disclosure, and may preferably be 0.1 to 5 mass%. Furthermore, the nonaqueous electrolyte solution of the present disclosure may contain a polymer, and the nonaqueous electrolyte may be quasi-solidified with a gelling agent or crosslinked polymer, as in the case of use in a nonaqueous electrolyte battery known as a polymer battery. Polymer solid electrolytes also include those containing a nonaqueous organic solvent as a plasticizer.

[0110] Nonaqueous Electrolyte Battery The nonaqueous electrolyte battery of the present disclosure includes at least the nonaqueous electrolyte of the present disclosure, a negative electrode, and a positive electrode. It is preferable that the battery further includes a separator, an outer casing, and the like. [Negative Electrode] The negative electrode is not particularly limited, but a material capable of reversibly inserting and extracting lithium ions, alkali metal ions such as sodium ions, and alkaline earth metal ions is preferably used. [Negative Electrode Active Material] For example, in the case of a lithium-ion secondary battery in which the cation is mainly lithium, the negative electrode active material constituting the negative electrode is capable of doping and dedoping lithium ions. Examples include a carbon material having a d value of the lattice plane (002 plane) of 0.340 nm or less in X-ray diffraction, a carbon material having a d value of the lattice plane (002 plane) of more than 0.340 nm in X-ray diffraction, an oxide of one or more metals selected from Si, Sn, and Al, an alloy containing one or more metals selected from Si, Sn, and Al, an alloy of one or more metals or alloys with lithium, and a lithium titanium oxide. These negative electrode active materials may be used alone or in combination of two or more. Furthermore, lithium metal, metal nitrides, tin compounds, conductive polymers, etc. may also be used as the negative electrode active material.

[0111] For example, in the case of a sodium-ion secondary battery in which the cation is primarily sodium, examples of the negative electrode active material that constitutes the negative electrode include sodium metal, alloys of sodium metal with other metals such as tin, intermetallic compounds, various carbon materials such as hard carbon, metal oxides such as titanium oxide, metal nitrides, tin (element), tin compounds, activated carbon, and conductive polymers. In addition to these, examples of the negative electrode active material that can be used include phosphorus (element) such as red phosphorus and black phosphorus, phosphorus compounds such as Co—P, Cu—P, Sn—P, Ge—P, and Mo—P, antimony (element), and antimony compounds such as Sb / C and Bi—Sb. These negative electrode active materials may be used alone or in combination of two or more.

[0112] [Negative Electrode Current Collector] The negative electrode has a negative electrode current collector. As the negative electrode current collector, for example, copper, stainless steel, nickel, titanium, or an alloy thereof can be used.

[0113] [Negative Electrode Active Material Layer] 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. Examples of the binder 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, etc. Examples of the conductive agent that can be used include carbon materials such as acetylene black, ketjen black, furnace black, and carbon fiber.

[0114] [Positive Electrode] The positive electrode is not particularly limited, but it is preferable to use a material that can reversibly insert and extract lithium ions, alkali metal ions such as sodium ions, or alkaline earth metal ions. [Positive Electrode Active Material] For example, when the cation is lithium, examples of the positive electrode material that can be used include lithium-containing transition metal composite oxides such as LiCoO2, LiNiO2, LiMnO2, and LiMn2O4, mixtures of these lithium-containing transition metal composite oxides with multiple transition metals such as Co, Mn, and Ni, lithium-containing transition metal composite oxides in which a portion of the transition metal has been substituted with a metal other than the transition metal, transition metal phosphate compounds called olivine such as LiFePO4, LiCoPO4, and LiMnPO4, oxides such as TiO2, VO5, and MoO3, sulfides such as TiS2 and FeS, conductive polymers such as polyacetylene, polyparaphenylene, polyaniline, and polypyrrole, activated carbon, radical-generating polymers, and carbon materials. In particular, it is possible to use a material containing at least one of the following: (A) a lithium transition metal composite oxide containing nickel or, in addition to nickel, one or more metals selected from the group consisting of manganese, cobalt, and aluminum, and having a layered structure; (B) a lithium manganese composite oxide having a spinel structure and containing nickel; (C) a lithium-containing olivine-type phosphate containing nickel; and (D) a lithium-excess layered transition metal oxide having a layered rock salt structure and containing nickel.

[0115] (A) Lithium Transition Metal Composite Oxide) Positive Electrode Active Material (A) Examples of lithium transition metal composite oxides containing nickel or nickel plus one or more metals selected from the group consisting of manganese, cobalt, and aluminum and having a layered structure include lithium-nickel composite oxide, lithium-nickel-cobalt composite oxide, lithium-nickel-cobalt-aluminum composite oxide, lithium-nickel-manganese composite oxide, and lithium-nickel-manganese-cobalt composite oxide. These lithium transition metal composite oxides may also be used in which some of the transition metal atoms constituting the main component are replaced with other elements such as Al, Ti, V, Cr, Fe, Cu, Zn, Mg, Ga, Zr, Si, B, Ba, Y, and Sn. Specific examples of lithium-nickel composite oxides include LiNiO 2 , LiNiO 2 to which different elements such as Mg, Zr, Al, and Ti have been added, and LiNiO 2 particle powders in which aluminum oxide is coated on a portion of the particle surface.

[0116] The lithium-nickel-cobalt composite oxide and the lithium-nickel-cobalt-aluminum composite oxide are represented by the following general formula [1-1]: Li a Ni 1-b-c Co b M 1 c O2 [1-1] In formula [1-1], M 1 is at least one element selected from the group consisting of Al, Fe, Mg, Zr, Ti, and B, and a satisfies the conditions of 0.9≦a≦1.2, and b and c satisfy the conditions of 0.1≦b≦0.3 and 0≦c≦0.1. These can be prepared, for example, in accordance with the manufacturing method described in JP-A-2009-137834. Specifically, LiNi 0.8 Co 0.2 O2 and LiNi 0.85 Co 0.10 Al 0.05 O2, LiNi 0.87 Co 0.10 Al 0.03 O2, LiNi 0.6 Co 0.3 Al 0.1 O2 and the like are preferred.

[0117] Specific examples of lithium-nickel-manganese composite oxides include LiNi 0.5 Mn 0.5 O2, LiCo 0.5 Mn 0.5 Examples of the lithium-nickel-manganese-cobalt composite oxide include lithium-containing composite oxides represented by the following general formula [1-2]: Li d Ni e Mn f Co g M 2 h [1-2] In formula [1-2], M 2 is at least one element selected from the group consisting of Al, Fe, Mg, Zr, Ti, B, and Sn, d is 0.9≦d≦1.2, and e, f, g, and h satisfy the conditions of e+f+g+h=1, 0<e≦0.9, 0<f≦0.5, 0<g≦0.5, and h≧0.

[0118] The lithium-nickel-manganese-cobalt composite oxide preferably contains manganese in the range shown in the general formula [1-2] in order to enhance the structural stability and improve the safety of lithium batteries at high temperatures, and more preferably contains cobalt in the range shown in the general formula [1-2] in order to enhance the high-rate characteristics of lithium ion batteries. Specifically, for example, a lithium-nickel-manganese-cobalt composite oxide having a charge / discharge range of 4.3 V or more is preferably used. 1 / 3 Mn 1 / 3 Co 1 / 3 ]O2 (hereinafter, sometimes referred to as "NCM111"), Li[Ni 0.45 Mn 0.35 Co 0.2 ]O2, Li[Ni 0.5 Mn 0.3 Co 0.2 ]O2, Li[Ni 0.6 Mn 0.2 Co 0.2 ]O2 (hereinafter, sometimes referred to as "NCM622"), Li[Ni 0.8 Mn 0.1 Co 0.1 ]O2 (hereinafter, sometimes referred to as "NCM811"), Li[Ni 0.49 Mn 0.3 Co0.2 Zr 0.01 ]O2, Li[Ni 0.49 Mn 0.3 Co 0.2 Mg 0.01 ]O2 and the like are preferred.

[0119] ((B) Lithium manganese composite oxide having a spinel structure) Positive electrode active material (B) Examples of lithium manganese composite oxides having a spinel structure include spinel-type lithium manganese composite oxides represented by the general formula [1-3]: Li j (Mn 2-k M 3 k )O4 [1-3] Formula [1-3], M 3 contains Ni and may contain at least one metal element selected from the group consisting of Co, Fe, Mg, Cr, Cu, Al, and Ti. j is 1.05≦j≦1.15, and k is 0<k≦0.20. Specifically, for example, LiMn 1.9 Ni 0.1 O4, LiMn 1.5 Ni 0.5 O4, etc.

[0120] ((C) Lithium-containing olivine-type phosphate) Positive electrode active material (C) Examples of the lithium-containing olivine-type phosphate include those represented by the following general formula [1-4]: LiFe 1-n M 4 n PO4 [1-4] Formula [1-4] In, M 4 contains Ni and may also contain at least one selected from Co, Mn, Cu, Zn, Nb, Mg, Al, Ti, W, Zr, and Cd, where n is 0<n≦1. Specifically, LiNiPO4 and the like are suitable examples.

[0121] ((D) Lithium-Rich Layered Transition Metal Oxide) Positive Electrode Active Material (D) Examples of lithium-rich layered transition metal oxides having a layered rock salt structure include those represented by the following general formula [1-5]: xLiM 5 O2・(1-x)Li2M 6O3 [1-5] In formula [1-5], x is a number satisfying 0<x<1, and M 5 has an average oxidation number of 3 + At least one metal element is M 6 has an average oxidation number of 4 + In formula [1-5], M is at least one metal element. 5 is preferably one or more trivalent metal elements selected from Mn, Ni, Co, Fe, V, and Cr, but may be divalent and tetravalent metals in equal amounts to make the average oxidation number trivalent.

[0122] In addition, in the formula [1-5], M 6 is preferably one or more metal elements selected from Mn, Zr and Ti. 5 and M 6 Nickel is always included in either of the following. 0.5 Mn 0.5 O2] 0.5[Li2MnO3] or 0.5[LiNi 1 / 3 Co 1 / 3 Mn 1 / 3 O2]・0.5[Li2MnO3], 0.5[LiNi 0.375 Co 0.25 Mn 0.375 O2]・0.5[Li2MnO3], 0.5[LiNi 0.375 Co 0.125 Fe 0.125 Mn 0.375 O2]・0.5[Li2MnO3], 0.45[LiNi 0.375 Co 0.25 Mn 0.375 Suitable examples of the positive electrode active material (D) represented by the general formula [1-5] include 0.10[LiTiO]·0.45[LiMnO]. The positive electrode active material (D) represented by the general formula [1-5] is known to exhibit high capacity upon high-voltage charging of 4.4 V (based on Li) or higher (see, for example, U.S. Patent No. 7,135,252). These positive electrode active materials can be prepared according to the manufacturing methods described in, for example, JP 2008-270201 A, WO 2013 / 118661 A, and JP 2013-030284 A.

[0123] For example, when the cation is sodium, the positive electrode material (positive electrode active material) is NaCrO2, NaFe 0.5 Co 0.5 O2, NaFe 0.4 Mn 0.3 Ni 0.3 O2, NaNi 0.5 Ti 0.3 Mn 0.2 O2, NaNi 1 / 3 Ti 1 / 3 Mn 1 / 3 O2, NaNi 0.33 Ti 0.33 Mn 0.16 Mg 0.17 O2, Na 2 / 3 Ni 1 / 3 Ti 1 / 6 Mn 1 / 2 O2, Na 2 / 3 Ni 1 / 3 Mn 2 / 3 Sodium-containing transition metal composite oxides such as O2, mixtures of multiple transition metals such as Co, Mn, and Ni in these sodium-containing transition metal composite oxides, sodium-containing transition metal composite oxides in which part of the transition metal has been replaced with a metal other than the transition metal, polyanion compounds such as NaFePO4, NaVPO4F, Na3V2(PO4)3, and Na2Fe2(SO4)3, and compounds with the composition formula Na a M b [Fe(CN)] c (M=Cr, Mn, Fe, Co, Ni, Cu, or Zn, and 0≦a≦2, 0.5≦b≦1.5, 0.5≦c≦1.5), oxides such as TiO, VO, and MoO, sulfides such as TiS and FeS, conductive polymers such as polyacetylene, polyparaphenylene, polyaniline, and polypyrrole, activated carbon, radical-generating polymers, carbon materials, and the like can be used.

[0124] [Positive Electrode Current Collector] The positive electrode has a positive electrode current collector. As the positive electrode current collector, for example, aluminum, stainless steel, nickel, titanium, or an alloy thereof can be used.

[0125] [Positive Electrode Active Material Layer] The positive electrode comprises, for example, a positive electrode active material layer formed on at least one surface of a positive electrode current collector. The positive electrode active material layer is composed of, for example, the above-described positive electrode active material, a binder, and, if necessary, a conductive agent. Examples of 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 the like. Examples of conductive agents 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. For the positive electrode, it is preferable to use acetylene black or ketjen black, which have low crystallinity.

[0126] [Method for producing electrodes (positive and negative electrodes)] The electrodes can be obtained, for example, by dispersing and kneading predetermined amounts of an active material, a binder, and, if necessary, a conductive agent in a solvent such as N-methyl-2-pyrrolidone (hereinafter also referred to as "NMP") or water, applying the resulting paste to a current collector, and drying to form an active material layer. The resulting electrode is preferably compressed by a method such as a roll press to adjust it to an electrode with an appropriate density.

[0127] [Separator] The nonaqueous electrolyte battery of the present disclosure may include a separator. Examples of separators used to prevent contact between the positive electrode and the negative electrode include nonwoven fabrics or porous sheets made of polyolefins such as polypropylene and polyethylene, cellulose, paper, or glass fiber. These films are preferably microporous so that the electrolyte can penetrate and ions can easily pass through. Examples of polyolefin separators include microporous polymer films such as porous polyolefin films, which electrically insulate the positive electrode and negative electrode and are permeable to lithium ions. Specific examples of 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 of the present disclosure may be impregnated into the separator and retained therein. There are no particular limitations on the impregnation method, and any known method may be used. Specifically, the electrolyte can be finally injected into a battery equipped with a positive electrode, a separator, and a negative electrode to impregnate the battery.

[0128] [Exterior Body] As the exterior body of the nonaqueous electrolyte battery of the present disclosure, for example, a coin-shaped, cylindrical, or rectangular metal can, or a laminated exterior body, etc. Suitable examples of metal can materials include nickel-plated steel plate, stainless steel plate, nickel-plated stainless steel plate, aluminum or its alloy, nickel, titanium, etc. As the laminated exterior body, for example, an aluminum laminate film, a SUS laminate film, or a laminate film of silica-coated polypropylene, polyethylene, etc., can be used.

[0129] The configuration of the nonaqueous electrolyte battery according to this embodiment is not particularly limited, and may be configured, for example, to include an electrode element in which a positive electrode and a negative electrode are arranged opposite each other, and a nonaqueous electrolyte, enclosed in an exterior body. The shape of the nonaqueous electrolyte battery is not particularly limited, and an electrochemical device having a shape such as a coin, a cylinder, a square, or an aluminum laminate sheet can be assembled from the above elements. A nonaqueous electrolyte battery containing the nonaqueous electrolyte of the present disclosure can be manufactured, for example, by impregnating a separator with the nonaqueous electrolyte, disposing the separator between the positive electrode and the negative electrode, and assembling the cell.

[0130] Hereinafter, the present disclosure will be described in more detail with reference to synthesis examples, examples, and comparative examples, but the scope of the present disclosure is not limited in any way by these synthesis examples, examples, and comparative examples.

[0131] Synthesis Example of Component (III): Synthesis Example 1-1 (Synthesis Example of Compound (1a) Represented by General Formula (1))

[0132] Lithium hydride (0.1 g, 13 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Subsequently, sulfuryl fluoride (1.2 g, 12 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 20 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1a) as a white solid (1.5 g, 73% yield). 1 H NMR (CD3CN) σ1.56, 5.18ppm 19 F NMR (CD3CN) σ40.8ppm

[0133] Synthesis Example 1-2 (Synthesis example of compound (1b) represented by general formula (1))

[0134] Phosphoryl chloride (1.6 g, 10 mmol) was added to oxazolidine-2,4-dione (1.0 g, 10 mmol) in 50 ml of acetonitrile, and the reaction solution was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added portionwise to the reaction solution, and the mixture was warmed to room temperature and stirred for 1 hour. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the intermediate N-dichlorophosphoryl oxazolidine-2,4-dione. Next, 50 ml of acetonitrile was added, and potassium fluoride (1.4 g, 24 mmol) was added, followed by stirring at room temperature for 23 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1b) (1.2 g, yield 66%). 1 H NMR (CD3CN) σ4.88ppm 19 F NMR (CD3CN) σ-72.0, -69.1ppm

[0135] Synthesis Example 1-3 (Synthesis example of compound (1c) represented by general formula (1))

[0136] Phosphoryl chloride (1.6 g, 10 mmol) was added to 5,5-dimethyloxazolidine-2,4-dione (1.3 g, 10 mmol) in 50 ml of acetonitrile, and the reaction solution was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added portionwise to the reaction solution, and the mixture was warmed to room temperature and stirred for 1 hour. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the intermediate N-dichlorophosphoryl-5,5-dimethyloxazolidine-2,4-dione. Next, 50 ml of 1,2-dichloroethane and propargyl alcohol (1.4 g, 25 mmol) were added, and the mixture was then ice-cooled. Subsequently, triethylamine (2.4 g, 24 mmol) was slowly added dropwise to the reaction solution so that the internal temperature did not exceed 5°C, and the mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was washed twice with 20 ml of 1 M aqueous hydrochloric acid, and the resulting organic layer was concentrated under reduced pressure to obtain the target compound (1c) (1.9 g, yield 66%). 1 H NMR (CD3CN) σ1.58, 2.99, 4.92ppm

[0137] Synthesis Example 1-4 (Synthesis example of compound (1d) represented by general formula (1))

[0138] Lithium hydride (0.1 g, 13 mmol) was added to 5,5-dimethyloxazolidine-2,4-dione (1.3 g, 10 mmol) in 50 mL of ethyl methyl carbonate, and the mixture was stirred for 15 hours. Sulfur trioxide (0.9 g, 11 mmol) was added to the suspension, and the mixture was stirred at room temperature for 30 minutes. The resulting suspension was filtered to obtain the target compound (1d) as a residue (2.0 g, yield 92%). 1 H NMR (CD3CN) σ1.55ppm

[0139] Synthesis Example 1-5 (Synthesis example of compound (1e) represented by general formula (1))

[0140] Lithium hydride (0.1 g, 13 mmol) was added to 5,5-bis(trifluoromethyl)oxazolidine-2,4-dione (2.4 g, 10 mmol) in 50 mL of ethyl methyl carbonate, and the mixture was stirred for 15 hours. Sulfur trioxide (0.9 g, 11 mmol) was added to the suspension, and the mixture was stirred at room temperature for 30 minutes. The resulting suspension was filtered to obtain the target compound (1e) as a residue (2.9 g, yield 89%). 19 F NMR (CD3CN) σ-72.8ppm

[0141] Synthesis Example 1-6 (Synthesis example of compound (1f) represented by general formula (1))

[0142] Lithium hydride (0.1 g, 13 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of ethyl methyl carbonate, and the mixture was stirred for 17 hours. Sulfur trioxide (0.9 g, 11 mmol) was added to the suspension, and the mixture was stirred at room temperature for 30 minutes. The resulting suspension was filtered to obtain the target compound (1f) as a residue (1.9 g, yield 91%). 1 H NMR (CD3CN) σ1.49, 4.83ppm

[0143] Synthesis Example 1-7 (Synthesis example of compound (1g) represented by general formula (1))

[0144] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, bis(fluorosulfonyl)imide (1.9 g, 10 mmol) was added, and the reaction solution was then cooled on ice. Subsequently, lithium hydride (0.1 g, 13 mmol) was added portionwise to the reaction solution, and the mixture was heated to 50°C and stirred for 18 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1 g) (2.3 g, yield 80%). 1 H NMR (CD3CN) σ1.50, 4.90ppm 19 F NMR (CD3CN) σ51.8ppm

[0145] Synthesis Example 1-8 (Synthesis example of compound (1h) represented by general formula (1))

[0146] Lithium (difluorophosphoryl) (fluorosulfonyl) imide (1.9 g, 10 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the reaction solution was then cooled on ice. Subsequently, lithium hydride (0.1 g, 13 mmol) was added portionwise to the reaction solution, and the mixture was heated to 50°C and stirred for 18 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1h) (2.2 g, yield 74%). 1 H NMR (CD3CN) σ1.48, 4.92ppm 19 F NMR (CD3CN) σ52.2, -72.1, -69.2ppm

[0147] Synthesis Example 1-9 (Synthesis example of compound (1i) represented by general formula (1))

[0148] Methanesulfonyl chloride (1.26 g, 11 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Sodium hydride (0.3 g, 13 mmol) was then added to the reaction mixture, which was then warmed to room temperature and stirred for 15 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1i) as a white solid (1.7 g, 84% yield). 1 H NMR (CD3CN) σ1.56, 3.12, 5.21ppm

[0149] Synthesis Example 1-10 (Synthesis example of compound (1j) represented by general formula (1))

[0150] Trifluoromethanesulfonyl chloride (1.85 g, 11 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Sodium hydride (0.3 g, 13 mmol) was then added to the reaction mixture, which was then warmed to room temperature and stirred for 15 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1j) as a white solid (2.0 g, yield 78%). 1 H NMR (CD3CN) σ1.47, 4.92ppm 19 F NMR (CD3CN) σ-80.1ppm

[0151] Synthesis Example 1-11 (Synthesis example of compound (1k) represented by general formula (1))

[0152] Methyl chlorosulfonate (1.43 g, 11 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Sodium hydride (0.3 g, 13 mmol) was then added to the reaction mixture, which was then warmed to room temperature and stirred for 15 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1k) as a white solid (1.6 g, yield 73%). 1 H NMR (CD3CN) σ1.53, 4.21, 5.17ppm

[0153] Synthesis Example 1-12 (Synthesis example of compound (1l) represented by general formula (1))

[0154] 2-Chloro-2-oxo-1,3,2-dioxaphospholane (1.56 g, 11 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Sodium hydride (0.3 g, 13 mmol) was then added to the reaction mixture, which was then warmed to room temperature and stirred for 20 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1l) as a white solid (2.0 g, 87% yield). 1 H NMR (CD3CN) σ1.51, 4.15, 4.79ppm

[0155] Synthesis Example 1-13 (Synthesis example of compound (1m) represented by general formula (1))

[0156] Diisopropyl chlorophosphate (2.2 g, 11 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, which was then warmed to room temperature and stirred for 14 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1m) as a white solid (2.7 g, 92% yield). 1 H NMR (CD3CN) σ1.43, 1.59, 4.15, 4.71ppm

[0157] Synthesis Example 1-14 (Synthesis example of compound (1n) represented by general formula (1))

[0158] Oxalyl chloride (1.5 g, 12 mmol) was added to fluorosulfonyl isocyanate (1.3 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was heated to 90°C and refluxed and stirred for 21 hours. Sodium fluoride (1.3 g, 31 mmol) was added to the resulting reaction solution, and the mixture was heated to 50°C and stirred for 13 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1n) as a white solid (1.5 g, yield 68%). 1 H NMR (CD3CN) σ1.43, 1.59, 4.15, 4.71ppm 19 F NMR (CD3CN) σ49.5, -88.2ppm

[0159] Synthesis Example 1-15 (Synthesis example of compound (1o) represented by general formula (1))

[0160] Lithium hydride (0.1 g, 13 mmol) was added to oxazolidine-2,4,5-trione (1.2 g, 10 mmol) in 50 mL of ethyl methyl carbonate, and the mixture was stirred for 15 hours. Sulfur trioxide (0.9 g, 11 mmol) was added to the suspension, and the mixture was stirred at room temperature for 30 minutes. The resulting suspension was filtered to obtain the target compound (1o) as a residue (1.8 g, yield 86%).

[0161] Synthesis Example 2-1 (Synthesis example of compound (2a) represented by general formula (2))

[0162] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, methyl chloroformate (1.1 g, 1.2 mmol) was added, and then sodium hydride (0.3 g, 13 mmol) was added portionwise at room temperature and stirred for 1 hour. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the intermediate N-methoxycarbonyl-5-methyloxazolidine-2,4-dione. Next, 50 ml of acetonitrile and 1.3 g (10 mmol) of lithium iodide were added, and the mixture was heated to 50°C and stirred for 20 hours. The reaction solution was concentrated under reduced pressure to obtain (2a) (1.3 g, yield 79%). 1 H NMR (CD3CN) σ1.57, 5.11ppm

[0163] Synthesis Example 2-2 (Synthesis example of compound (2b) represented by general formula (2))

[0164] To oxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 12 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 19 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-chlorocarbonyl-oxazolidine-2,4-dione as an intermediate. Next, 50 ml of acetonitrile was added and the mixture was ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added, and hydrogen sulfide (0.3 g, 10 mmol) was introduced into the reaction mixture. The mixture was warmed to room temperature and stirred for 12 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-thiolcarbonyl-oxazolidine-2,4-dione as an intermediate. Next, 30 ml of water was added, followed by the addition of potassium peroxymonosulfate (3.8 g, 25 mmol) and potassium chloride (0.7 g, 10 mmol), and the mixture was stirred at room temperature for 2 hours. Sodium fluoride (0.4 g, 10 mmol) was then added, and the mixture was stirred at room temperature for 24 hours. The resulting reaction solution was washed with 30 ml of ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure to obtain the target compound (2b) (0.4 g, 19% yield). 1 H NMR (CD3CN) σ5.04ppm 19 F NMR (CD3CN) σ49.3ppm

[0165] Synthesis Example 2-3 (Synthesis example of compound (2c) represented by general formula (2))

[0166] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 19 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-chlorocarbonyl-5-methyloxazolidine-2,4-dione as an intermediate. Next, 50 ml of acetonitrile was added, and then lithium fluorosulfate (1.1 g, 10 mmol) was added, and the mixture was stirred at room temperature for 23 hours. The resulting reaction mixture was concentrated under reduced pressure to obtain the target compound (2c) (1.6 g, yield 66%). 1 H NMR (CD3CN) σ1.65, 5.37ppm 19 F NMR (CD3CN) σ47.3ppm

[0167] Synthesis Example 2-4 (Synthesis example of compound (2d) represented by general formula (2))

[0168] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 19 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-chlorocarbonyl-5-methyloxazolidine-2,4-dione as an intermediate. Next, 50 ml of acetonitrile was added, followed by the addition of dichlorohydroxyphosphine (1.2 g, 10 mmol), and the mixture was stirred at room temperature for 23 hours. Subsequently, sodium fluoride (0.8 g, 20 mmol) was added, and the mixture was stirred at room temperature for 25 hours. The resulting reaction mixture was concentrated under reduced pressure to obtain the target compound (2d) (0.9 g, yield 40%). 1 H NMR (CD3CN) σ1.61, 5.21ppm 19 F NMR (CD3CN) σ-71.5, -68.6ppm

[0169] Synthesis Example 2-5 (Synthesis example of compound (2e) represented by general formula (2))

[0170]

[0171] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 19 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-chlorocarbonyl-5-methyloxazolidine-2,4-dione as an intermediate. Next, 50 ml of acetonitrile was added, and then 2-propynyl phosphite (2.0 g, 10 mmol) was added, and the mixture was stirred at room temperature for 23 hours. The resulting reaction mixture was concentrated under reduced pressure to obtain the target compound (2e) (1.5 g, yield 48%). 1 H NMR (CD3CN) σ1.57, 5.11ppm

[0172] Synthesis Example 2-6 (Synthesis example of compound (2f) represented by general formula (2))

[0173] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 20 hours. Sodium fluoride (0.6 g, 14 mmol) was added to the resulting suspension, and the mixture was stirred at room temperature for 15 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (2f) as a white solid (1.0 g, yield 60%). 1 H NMR (CD3CN) σ1.51, 4.95ppm 19 F NMR (CD3CN) σ-68.2ppm

[0174] Synthesis Example 3-1 (Synthesis example of compound (3a) represented by general formula (3))

[0175] To oxazolidine-2,4-dione (1.0 g, 10 mmol) in 50 mL of acetonitrile was added fluorosulfonyl isocyanate (1.4 g, 11 mmol), and then lithium hydride (0.1 g, 13 mmol) was added portionwise at room temperature and stirred for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (3a) (2.1 g, yield 91%). 1 H NMR (CD3CN) σ4.76ppm 19 F NMR (CD3CN) σ49.5ppm

[0176] Synthesis Example 3-2 (Synthesis example of compound (3b) represented by general formula (3))

[0177] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile was added fluorosulfonyl isocyanate (1.4 g, 11 mmol), and then sodium hydride (0.3 g, 13 mmol) was added portionwise at room temperature and stirred for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (3b) (2.4 g, yield 88%). 1 H NMR (CD3CN) σ1.55, 5.09ppm 19 F NMR (CD3CN) σ49.7ppm

[0178] Synthesis Example 3-3 (Synthesis example of compound (3c) represented by general formula (3))

[0179] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, fluorosulfonyl isocyanate (1.4 g, 11 mmol) was added, and then lithium hydride (0.2 g, 25 mmol) was added portionwise at room temperature and stirred for 3 hours. Next, propargyl alcohol (0.7 g, 12 mmol) was added, and the mixture was heated to 50°C and stirred for 5 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (3c) (2.5 g, yield 85%). 1 H NMR (CD3CN) σ1.55, 3.65, 5.09ppm

[0180] Synthesis Example 3-4 (Synthesis example of compound (3d) represented by general formula (3))

[0181] Difluorophosphoryl isocyanate (1.4 g, 11 mmol) was added to oxazolidine-2,4-dione (1.0 g, 10 mmol) in 50 mL of acetonitrile, and then lithium hydride (0.1 g, 13 mmol) was added portionwise at room temperature, followed by stirring for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (3d) (2.1 g, yield 91%). 1 H NMR (CD3CN) σ4.76ppm 19 F NMR (CD3CN) σ -74.7, -71.8ppm

[0182] Synthesis Example 3-5 (Synthesis example of compound (3e) represented by general formula (3))

[0183] Diethyl phosphoryl isocyanate (2.0 g, 11 mmol) was added to 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and then lithium hydride (0.1 g, 13 mmol) was added portionwise at room temperature, followed by stirring for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (3e) (2.6 g, yield 83%). 1 H NMR (CD3CN) σ1.55, 1.59, 4.27, 5.09ppm

[0184] Synthesis Example 3-6 (Synthesis example of compound (3f) represented by general formula (3))

[0185] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 5 hours. To the resulting suspension, iminodiacetonitrile (1.0 g, 10 mmol) was added portionwise under ice-cooling. The mixture was warmed to room temperature and stirred for 17 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (3f) as a white solid (1.5 g, yield 61%). 1 H NMR (CD3CN) σ1.54, 4.22, 5.08ppm

[0186] Synthesis Example 4-1 (Synthesis example of compound (4a) represented by general formula (4))

[0187] To oxazolidine-2,4-dione (1.0 g, 10 mmol) in 50 mL of acetonitrile was added triphosgene (1.5 g, 5.1 mmol), and then sodium hydride (0.3 g, 13 mmol) was added portionwise at room temperature, followed by stirring for 21 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (4a) (1.0 g, yield 89%). 1 H NMR (CD3CN) σ4.84ppm

[0188] Synthesis Example 4-2 (Synthesis example of compound (4b) represented by general formula (4))

[0189] To 5-methyloxazolidine-2,4-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile was added triphosgene (1.5 g, 5.1 mmol), and then sodium hydride (0.3 g, 13 mmol) was added portionwise at room temperature, followed by stirring for 21 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (4b) (1.1 g, yield 90%). 1 H NMR (CD3CN) σ1.57, 5.11ppm

[0190] Synthesis Example 4-3 (Synthesis example of compound (4c) represented by general formula (4))

[0191] Compound (4c) was synthesized (1.3 g, yield 85%) in the same manner as in the synthesis example for compound (4a), except that 10 mmol of 5,5-difluorooxazolidine-2,4-dione was used instead of 10 mmol of oxazolidine-2,4-dione. 19 F NMR (CD3CN) σ-85.2ppm

[0192] Synthesis Example 4-4 (Synthesis example of compound (4d) represented by general formula (4))

[0193] Compound (4d) was synthesized (1.3 g, yield 85%) in the same manner as in the synthesis example for compound (4a), except that 10 mmol of 5,5-dimethyloxazolidine-2,4-dione was used instead of 10 mmol of oxazolidine-2,4-dione. 1 H NMR (CD3CN) σ1.56ppm

[0194] Synthesis Example 5-1 (Synthesis example of compound (5a) represented by general formula (5))

[0195] Lithium hydride (0.1 g, 13 mmol) was added to 4,4-dimethyloxazolidine-2,5-dione (1.3 g, 10 mmol) in 50 mL of ethyl methyl carbonate, and the mixture was stirred for 15 hours. Sulfur trioxide (0.9 g, 11 mmol) was added to the suspension, and the mixture was stirred at room temperature for 30 minutes. The resulting suspension was filtered to obtain the target compound (5a) as a residue (1.9 g, yield 88%). 1 H NMR (CD3CN) σ1.61ppm

[0196] Synthesis Example 5-2 (Synthesis example of compound (5b) represented by general formula (5))

[0197] Lithium hydride (0.1 g, 13 mmol) was added to 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Subsequently, sulfuryl fluoride (1.2 g, 12 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 20 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (5b) as a white solid (1.4 g, yield 68%). 1 H NMR (CD3CN) σ1.57, 5.21ppm 19 F NMR (CD3CN) σ41.0ppm

[0198] Synthesis Example 5-3 (Synthesis example of compound (5c) represented by general formula (5))

[0199] Phosphoryl chloride (1.6 g, 10 mmol) was added to 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, and the reaction solution was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added portionwise to the reaction solution, and the mixture was warmed to room temperature and stirred for 1 hour. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the intermediate N-dichlorophosphoryl-4-methyloxazolidine-2,5-dione. Next, 50 ml of acetonitrile was added, and potassium fluoride (1.4 g, 24 mmol) was added, followed by stirring at room temperature for 23 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (5c) (1.3 g, yield 66%). 1 H NMR (CD3CN) σ1.53, 4.96ppm 19 F NMR (CD3CN) σ -71.8, -68.9ppm

[0200] Synthesis Example 5-4 (Synthesis example of compound (5d) represented by general formula (5))

[0201] Dimethyl chlorophosphate (1.6 g, 11 mmol) was added to 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, which was then warmed to room temperature and stirred for 14 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (1m) as a white solid (2.0 g, 86% yield). 1 H NMR (CD3CN) σ1.59, 4.29, 4.79ppm

[0202] Synthesis Example 6-1 (Synthesis example of compound (6a) represented by general formula (6))

[0203] To 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, methyl chloroformate (1.1 g, 1.2 mmol) was added, and then sodium hydride (0.3 g, 13 mmol) was added portionwise at room temperature and stirred for 1 hour. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the intermediate N-methoxycarbonyl-4-methyloxazolidine-2,5-dione. Next, 50 ml of acetonitrile and lithium iodide (1.3 g, 10 mmol) were added, and the mixture was heated to 50°C and stirred for 20 hours. The reaction mixture was concentrated under reduced pressure to obtain the target compound (6a) (1.2 g, 70% yield). 1 H NMR (CD3CN) σ1.63, 5.28ppm

[0204] Synthesis Example 6-2 (Synthesis example of compound (6b) represented by general formula (6))

[0205] To 4,4-dimethyloxazolidine-2,5-dione (1.3 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Sodium hydride (0.3 g, 13 mmol) was then added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 20 hours. Sodium fluoride (0.6 g, 14 mmol) was added to the resulting suspension, and the mixture was stirred at room temperature for 15 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (6b) as a white solid (1.0 g, yield 57%). 1 H NMR (CD3CN) σ1.51ppm 19 F NMR (CDCN) σ-62.3 ppm

[0206] Synthesis Example 6-3 (Synthesis example of compound (6c) represented by general formula (6))

[0207] To oxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 19 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-chlorocarbonyl-oxazolidine-2,5-dione as an intermediate. Next, 50 ml of acetonitrile was added, and the mixture was ice-cooled. Sodium hydride (0.3 g, 13 mmol) was added, and hydrogen sulfide (0.3 g, 10 mmol) was introduced into the reaction mixture. The mixture was warmed to room temperature and stirred for 12 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-thiolcarbonyl-oxazolidine-2,5-dione as an intermediate. Next, 30 ml of water was added, followed by the addition of potassium peroxymonosulfate (3.8 g, 25 mmol) and potassium chloride (0.7 g, 10 mmol), and the mixture was stirred at room temperature for 3 hours. 30 ml of ethyl acetate was added to the resulting reaction solution for washing, and anhydrous sodium sulfate was added to the organic layer for drying and filtration. The resulting filtrate was concentrated under reduced pressure to obtain N-chlorosulfonylcarbonyl-oxazolidine-2,5-dione as an intermediate. 50 ml of acetonitrile was then added and the mixture was ice-cooled. Propargyl alcohol (0.6 g, 10 mmol) was then added, sodium hydride (0.3 g, 13 mmol) was added, and the mixture was warmed to room temperature and stirred for 20 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (6c) (0.3 g, 12% yield). 1 H NMR (CD3CN) σ2.96, 4.57, 4.94ppm

[0208] Synthesis Example 6-4 (Synthesis example of compound (6d) represented by general formula (6))

[0209] To 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, triphosgene (1.5 g, 5.1 mmol) was added, and the mixture was then ice-cooled. Subsequently, sodium hydride (0.3 g, 13 mmol) was added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 19 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain N-chlorocarbonyl-4-methyloxazolidine-2,5-dione as an intermediate. Next, 50 ml of acetonitrile was added and the mixture was ice-cooled. Subsequently, difluorophosphoric acid (1.0 g, 10 mmol) and sodium hydride (0.3 g, 13 mmol) were added to the reaction mixture, and the mixture was warmed to room temperature and stirred for 18 hours. The resulting suspension was filtered and concentrated under reduced pressure to obtain the target compound (6d) (1.1 g, yield 45%). 1 H NMR (CD3CN) σ1.65, 5.31ppm 19 F NMR (CD3CN) σ-73.2, -70.3ppm

[0210] Synthesis Example 7-1 (Synthesis example of compound (7a) represented by general formula (7))

[0211] To oxazolidine-2,5-dione (1.0 g, 10 mmol) in 50 mL of acetonitrile was added fluorosulfonyl isocyanate (1.4 g, 11 mmol), and then lithium hydride (0.1 g, 13 mmol) was added portionwise at room temperature and stirred for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (7a) (2.0 g, yield 87%). 1 H NMR (CD3CN) σ4.82ppm 19 F NMR (CD3CN) σ50.4ppm

[0212] Synthesis Example 7-2 (Synthesis example of compound (7b) represented by general formula (7))

[0213] To 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 mL of acetonitrile was added bis(2,2,2-trifluoroethyl)phosphoryl isocyanate (3.1 g, 11 mmol), and then lithium hydride (0.1 g, 13 mmol) was added portionwise at room temperature, followed by stirring for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (7b) (3.0 g, yield 71%). 1 H NMR (CD3CN) σ1.55, 4.27, 5.09ppm 19 F NMR (CD3CN) σ-81.4ppm

[0214] Synthesis Example 7-3 (Synthesis example of compound (7c) represented by general formula (7))

[0215] Difluorophosphoryl isocyanate (1.4 g, 11 mmol) was added to 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile, and the mixture was stirred for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to give the target compound (7c) (2.0 g, yield 86%). 1 H NMR (CD3CN) σ1.61, 5.23ppm 19 F NMR (CD3CN) σ-74.3, -71.4ppm

[0216] Synthesis Example 8-1 (Synthesis example of compound (8a) represented by general formula (8))

[0217] To 4-methyloxazolidine-2,5-dione (1.2 g, 10 mmol) in 50 ml of acetonitrile was added triphosgene (1.5 g, 5.1 mmol), and then sodium hydride (0.3 g, 13 mmol) was added portionwise at room temperature, followed by stirring for 21 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure to obtain the target compound (8a) (1.1 g, yield 82%). 1 H NMR (CD3CN) σ1.62, 5.22ppm

[0218] Synthesis Example 8-2 (Synthesis example of compound (8b) represented by general formula (8))

[0219] Compound (8b) was synthesized (1.2 g, yield 78%) in the same manner as in the synthesis example for compound (8a) above, except that 10 mmol of 4,4-ditrifluoromethyloxazolidine-2,5-dione was used instead of 10 mmol of 4-methyloxazolidine-2,5-dione. 19 F NMR (CD3CN) σ-83.2ppm

[0220] Comparative Example Compounds: In the following Examples and Comparative Examples, the following compounds were used as control compounds.

[0221] Here, comparative compound 1 corresponds to the compound used in Example 1 of Patent Document 1 or Example 23 of Patent Document 2, comparative compound 2 corresponds to the compound used in Example 2 of Patent Document 1 or Example 24 of Patent Document 2, comparative compound 3 corresponds to the compound used in Example 3 of Patent Document 1 or Example 25 of Patent Document 2, comparative compound 4 corresponds to the compound used in Example 4 of Patent Document 1 or Example 26 of Patent Document 2, comparative compound 5 corresponds to the compound used in Examples 1 to 3 of Patent Document 3, comparative compound 6 corresponds to the compound used in Example 5 of Patent Document 3, and comparative compound 7 corresponds to the compound used in Example 4 of Patent Document 3.

[0222] [Preparation of Nonaqueous Electrolytes in Examples and Comparative Examples] Comparative Example 1-1 (Preparation of Comparative Nonaqueous Electrolyte 0 as Base) A solvent in which EC, DMC, and EMC were mixed at a volume ratio of EC:DMC:EMC = 2.5:3.5:4 was used as the nonaqueous organic solvent, and LiPF6 was dissolved as a solute in the solvent so that the content in the nonaqueous electrolyte was 1.00 mol / L to prepare Comparative Nonaqueous Electrolyte 0.

[0223] Examples 1-1 to 1-15 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compounds shown in Table 1 were dissolved as component (III) in the amounts shown in Table 1.

[0224] Comparative Examples 1-2 to 1-8 Comparative nonaqueous electrolyte solutions 1 to 7 were prepared in the same manner as in Example 1-1, except that comparative compounds 1 to 7 shown in Table 1 were dissolved in place of component (III) to give the contents shown in Table 1.

[0225] <Preparation of non-aqueous electrolyte secondary battery> (Preparation of NCM811 positive electrode) LiNi 0.8 Mn 0.1 Co 0.1 92.0 mass% of O2 powder was mixed with 3.5 mass% of polyvinylidene fluoride (hereinafter also referred to as "PVDF") as a binder and 4.5 mass% of acetylene black as a conductive material, and further N-methyl-2-pyrrolidone (hereinafter also referred to as "NMP") was added to LiNi 0.8 Mn 0.1 Co 0.1 The positive electrode active material layer was formed on the current collector by punching out a 4 cm × 5 cm piece of aluminum foil (A1085) with the paste applied to both sides.

[0226] (Fabrication of Graphite Negative Electrode) 97% by mass of natural graphite powder was mixed with 2% by mass of styrene butadiene rubber (hereinafter also referred to as "SBR"), 1% by mass of sodium carboxymethyl cellulose (hereinafter also referred to as "CMC"), and water to prepare a negative electrode composite paste. This paste was applied to copper foil, dried and pressed, and then punched out to 4.5 cm x 5.5 cm to obtain a test graphite negative electrode having a negative electrode active material layer formed on a current collector.

[0227] (Preparation of Silicon-Containing Graphite (Also Described as "Si-Graphite") Negative Electrode) 85% by mass of artificial graphite powder was mixed with 7% by mass of nanosilicon, 3% by mass of conductive material (HS-100 manufactured by Denka), 2% by mass of carbon nanofiber (VGCF manufactured by Showa Denko), 2% by mass of SBR, 1% by mass of CMC, and water to prepare a negative electrode composite paste. This paste was applied to copper foil, dried, pressed, and then punched out to 4.5 cm x 5.5 cm to obtain a test silicon-containing graphite negative electrode having a negative electrode active material layer formed on a current collector.

[0228] (Preparation of Nonaqueous Electrolyte Battery) In an argon atmosphere with a dew point of −50° C. or less, a terminal was welded to the above-mentioned NCM811 positive electrode, and then the positive electrode was sandwiched between two polyethylene separators (5 cm × 6 cm). The outer surface of the separator was further sandwiched between two graphite negative electrodes or silicon-containing graphite negative electrodes previously welded to terminals, with the negative electrode active material surface facing the positive electrode active material surface. These were then placed in an aluminum laminate bag with an opening on one side, and the nonaqueous electrolyte prepared above was vacuum-injected into the bag. The opening was then heat-sealed to prepare aluminum laminate nonaqueous electrolyte batteries according to the examples and comparative examples shown in the tables below.

[0229] [Evaluation Conditions] (Initial Charge / Discharge) Each of the nonaqueous electrolyte batteries (cells) prepared as described above was left to stand for 12 hours (impregnation time: 12 hours) at an ambient temperature of 25° C., and then conditioned under the following conditions at an ambient temperature of 25° C. That is, as the initial charge / discharge, the battery was charged at a constant current / constant voltage of 0.1 C rate (9 mA) to an upper charge voltage of 4.3 V, and discharged at a constant current of 0.2 C rate to a discharge cut-off voltage of 2.7 V. Thereafter, the battery was charged at a constant current / constant voltage of 0.2 C rate to an upper charge voltage of 4.3 V, and discharged at a constant current of 0.2 C rate to a discharge cut-off voltage of 2.7 V. This charge / discharge cycle was repeated three times.

[0230] (Initial Resistance Measurement) The cell that had been subjected to the above conditioning was charged to 4.3 V at 25° C. and a rate of 0.2 C, and then impedance measurement was carried out in an environment of −20° C. to measure the resistance value.

[0231] (Cycle Test) A charge / discharge test was carried out at an ambient temperature of 25°C on the cells whose initial resistances had been measured, and the cycle characteristics were evaluated. A charge / discharge cycle was repeated at a current value of 90 mA using a constant current / constant voltage method, with an upper charge voltage limit of 4.3 V and a lower discharge voltage limit of 2.7 V. The discharge capacity retention rate at the 400th cycle in the charge / discharge test at an ambient temperature of 25°C was calculated as follows to evaluate the degree of cell deterioration. The "discharge capacity retention rate after cycling," expressed as the discharge capacity retention rate at the 400th cycle, was calculated using the following formula. The discharge capacity at the first cycle in the charge / discharge test at an ambient temperature of 25°C was defined as the initial discharge capacity. Discharge capacity retention rate after cycling (%) = (discharge capacity at the 400th cycle / initial discharge capacity) x 100

[0232] (Evaluation of Gas Generation Amount) Before and after the above cycle characteristic evaluation, the cell volume was measured by Archimedes' method using silicone oil (silicone oil KF54, manufactured by Shin-Etsu Chemical Co., Ltd.), and the gas generation amount V (unit: cm 3 ) (gas generation amount V = cell volume V2 after cycle characteristic evaluation - cell volume V1 before cycle characteristic evaluation) was calculated. Based on this gas generation amount V, the "cycle test gas generation amount" was evaluated.

[0233] The initial resistance and capacity retention rate in the cycle test were evaluated for the nonaqueous electrolyte solutions 1-1, 1-2-1 to 1-2-5, 1-3 to 1-15 prepared above, and the comparative nonaqueous electrolyte solutions 0 to 7, as described above, and the results are shown in the following Table 1. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and capacity retention rate in the cycle test when comparative nonaqueous electrolyte solution 0 was used were 100.

[0234]

[0235] From the results shown in Table 1, it can be seen that by including the compound represented by general formula (1) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0236] Comparative Example 2-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 0 as Base) The comparative non-aqueous electrolyte solution was the same as the comparative non-aqueous electrolyte solution 0 prepared in Comparative Example 1-1.

[0237] Examples 2-1 to 2-6 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compound shown in Table 2 was dissolved as component (III) in the amount shown in Table 2.

[0238] Comparative Examples 2-2 to 2-8 Comparative nonaqueous electrolyte solutions according to Comparative Examples 2-2 to 2-8 are similar to the comparative nonaqueous electrolyte solutions 1 to 7 prepared in Comparative Examples 1-2 to 1-8.

[0239] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 2-1 to 2-6 and the comparative nonaqueous electrolyte solutions 0 to 7 prepared as described above were evaluated as described above, and the results are shown in the following Table 2. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 0 was used were evaluated as 100.

[0240]

[0241] From the results shown in Table 2, it can be seen that by including the compound represented by general formula (2) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0242] Comparative Example 3-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 0 as Base) This is the same as the comparative non-aqueous electrolyte solution 0 prepared in Comparative Example 1-1.

[0243] Examples 3-1-1 to 3-1-5 and 3-2 to 3-6 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compounds shown in Table 3 were dissolved as component (III) in the amounts shown in Table 3.

[0244] Comparative Examples 3-2 to 3-8 Comparative nonaqueous electrolyte solutions according to Comparative Examples 3-2 to 3-8 are similar to the comparative nonaqueous electrolyte solutions 1 to 7 prepared in Comparative Examples 1-2 to 1-8.

[0245] The initial resistance and capacity retention rate in the cycle test were evaluated for the nonaqueous electrolyte solutions 3-1-1 to 3-1-5 and 3-2 to 3-6 prepared above, and the comparative nonaqueous electrolyte solutions 0 to 7, as described above, and the results are shown in Table 3 below. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and capacity retention rate in the cycle test when comparative nonaqueous electrolyte solution 0 was used were 100.

[0246]

[0247] From the results shown in Table 3, it can be seen that by including the compound represented by general formula (3) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0248] Comparative Example 4-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 0 as Base) The comparative non-aqueous electrolyte solution was the same as the comparative non-aqueous electrolyte solution 0 prepared in Comparative Example 1-1.

[0249] Examples 4-1, 4-2-1 to 4-2-5, 4-3, and 4-4 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compounds shown in Table 4 were dissolved as component (III) in the amounts shown in Table 4.

[0250] Comparative Examples 4-2 to 4-8 The comparative nonaqueous electrolyte solutions according to Comparative Examples 4-2 to 4-8 are the same as the comparative nonaqueous electrolyte solutions 1 to 7 prepared in Comparative Examples 1-2 to 1-8.

[0251] The initial resistance and capacity retention rate in the cycle test were evaluated for the nonaqueous electrolyte solutions 4-1, 4-2-1 to 4-2-5, 4-3, and 4-4 prepared above, and the comparative nonaqueous electrolyte solutions 0 to 7, as described above, and the results are shown in Table 4. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and capacity retention rate in the cycle test when comparative nonaqueous electrolyte solution 0 was used were 100.

[0252]

[0253] From the results shown in Table 4, it can be seen that by including the compound represented by general formula (4) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0254] Comparative Example 5-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 0 as Base) This is the same as the comparative non-aqueous electrolyte solution 0 prepared in Comparative Example 1-1.

[0255] Examples 5-1-1 to 5-1-5 and 5-2 to 5-4 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compounds shown in Table 5 were dissolved as component (III) to the contents shown in Table 5.

[0256] Comparative Examples 5-2 to 5-8 Comparative nonaqueous electrolyte solutions according to Comparative Examples 5-2 to 5-8 are similar to the comparative nonaqueous electrolyte solutions 1 to 7 prepared in Comparative Examples 1-2 to 1-8.

[0257] The initial resistance and capacity retention rate in the cycle test were evaluated for the nonaqueous electrolyte solutions 5-1-1 to 5-1-5 and 5-2 to 5-4 prepared above, and the comparative nonaqueous electrolyte solutions 0 to 7, as described above, and the results are shown in Table 5. Note that these values ​​are relative values, and evaluation was performed assuming that the initial resistance and capacity retention rate in the cycle test when comparative nonaqueous electrolyte solution 0 was used were 100.

[0258]

[0259] From the results shown in Table 5, it can be seen that by including the compound represented by general formula (5) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0260] Comparative Example 6-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 0 as Base) This is the same as the comparative non-aqueous electrolyte solution 0 prepared in Comparative Example 1-1.

[0261] Examples 6-1 to 6-4 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compounds shown in Table 6 were dissolved as component (III) in the amounts shown in Table 6.

[0262] Comparative Examples 6-2 to 6-8 The comparative nonaqueous electrolyte solutions according to Comparative Examples 6-2 to 6-8 are similar to the comparative nonaqueous electrolyte solutions 1 to 7 prepared in Comparative Examples 1-2 to 1-8.

[0263] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 6-1 to 6-4 and the comparative nonaqueous electrolyte solutions 0 to 7 prepared as described above were evaluated as described above, and the results are shown in the following Table 6. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the comparative nonaqueous electrolyte solution 0 were evaluated as 100.

[0264]

[0265] From the results shown in Table 6, it can be seen that by including the compound represented by general formula (6) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0266] Comparative Example 7-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 0 as Base) This is the same as the comparative non-aqueous electrolyte solution 0 prepared in Comparative Example 1-1.

[0267] Examples 7-1 to 7-3 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compounds shown in Table 7 were dissolved as component (III) in the amounts shown in Table 7.

[0268] Comparative Examples 7-2 to 7-8 Comparative nonaqueous electrolyte solutions according to Comparative Examples 7-2 to 7-8 are similar to the comparative nonaqueous electrolyte solutions 1 to 7 prepared in Comparative Examples 1-2 to 1-8.

[0269] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 7-1 to 7-3 and the comparative nonaqueous electrolyte solutions 0 to 7 prepared as described above were evaluated as described above, and the results are shown in the following Table 7. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 0 was used were evaluated as 100.

[0270]

[0271] From the results shown in Table 7, it can be seen that by including the compound represented by general formula (7) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0272] Comparative Example 8-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 0 as Base) This is the same as the comparative non-aqueous electrolyte solution 0 prepared in Comparative Example 1-1.

[0273] Examples 8-1-1 to 8-1-5 and 8-2 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 0, except that the compounds shown in Table 8 were dissolved as component (III) to the contents shown in Table 8.

[0274] Comparative Examples 8-2 to 8-8 The comparative nonaqueous electrolyte solutions according to Comparative Examples 8-2 to 8-8 are similar to the comparative nonaqueous electrolyte solutions 1 to 7 prepared in Comparative Examples 1-2 to 1-8.

[0275] The initial resistance and capacity retention rate in the cycle test were evaluated for the nonaqueous electrolyte solutions 8-1-1 to 8-1-5 and 8-2 prepared above, and the comparative nonaqueous electrolyte solutions 0 to 7, as described above, and the results are shown in Table 8. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and capacity retention rate in the cycle test when comparative nonaqueous electrolyte solution 0 was used were 100.

[0276]

[0277] From the results shown in Table 8, it can be seen that by including the compound represented by general formula (8) as component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0278] Comparative Example 9-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 9-0 as Base) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive, and they were mixed so that the volume ratio of EC:FEC:DMC:EMC was 3:0.2:3:3.8. Next, LiPF was added and dissolved as a solute so that the content in the non-aqueous electrolyte solution was 1.00 mol / L, thereby preparing comparative non-aqueous electrolyte solution 9-0.

[0279] Examples 9-1 to 9-19 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 9-0, except that the compounds shown in Table 9 were dissolved as component (III) to the contents shown in Table 9.

[0280] Comparative Examples 9-2 to 9-8 Comparative nonaqueous electrolyte solutions 9-1 to 9-7 were prepared in the same manner as in Example 9-1, except that comparative compounds 1 to 7 shown in Table 9 were dissolved in place of component (III) to the contents shown in Table 9.

[0281] For the nonaqueous electrolyte solutions 9-1 to 9-19 and the comparative nonaqueous electrolyte solutions 9-0 to 9-7 prepared as described above, a nonaqueous electrolyte battery was used in which Si-graphite was used instead of graphite as the negative electrode active material, and the initial resistance and capacity retention rate in the cycle test were evaluated as described above, and the results are shown in Table 9 below. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and capacity retention rate in the cycle test when comparative nonaqueous electrolyte solution 0 was used are 100.

[0282]

[0283] From the results shown in Table 9, it can be seen that by including component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as a negative electrode active material exhibits excellent cycle characteristics and also excellent initial resistance characteristics compared to when an additive disclosed in the prior art is used.

[0284] Comparative Example 10-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 10-0 as Base) This is the same as the comparative non-aqueous electrolyte solution 9-0 prepared in Comparative Example 9-1.

[0285] Examples 10-1 to 10-19 Non-aqueous electrolyte solutions according to each example were prepared in the same manner as in the comparative non-aqueous electrolyte solution 10-0, except that the compounds shown in Table 10 were dissolved as component (III) to the contents shown in Table 10.

[0286] The amounts of gas generated in the cycle test for the nonaqueous electrolyte solutions 10-1 to 10-19 and the comparative nonaqueous electrolyte solution 10-0 prepared as described above were evaluated as described above, and the results are shown in the following Table 10. Note that this value is a relative value, and the amount of gas generated in the cycle test when the comparative nonaqueous electrolyte solution 10-0 was used was evaluated as 100.

[0287]

[0288] From the results shown in Table 10, it can be seen that by containing component (III) of the present disclosure, the amount of gas generated in a nonaqueous electrolyte battery using graphite as the negative electrode active material is suppressed during a cycle test.

[0289] Comparative Example 11-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 8 as Base) A solvent in which EC, DMC, and EMC were mixed at a volume ratio of EC:DMC:EMC=3:3:4 was used as the non-aqueous organic solvent, and LiPF was dissolved in the solvent as a solute so that the content in the non-aqueous electrolyte solution was 1.00 mol / L. Furthermore, VC and DFOB were each dissolved as other additives so that the contents were as shown in Table 11 below, to prepare comparative non-aqueous electrolyte solution 8.

[0290] Examples 11-1 to 11-14 and Comparative Examples 11-2 to 11-8 Component (III) or a comparative compound shown in Table 11 was dissolved in the comparative nonaqueous electrolyte solution 8 to the content shown in Table 11, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0291] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 11-1 to 11-14 and the comparative nonaqueous electrolyte solutions 8 to 15 prepared as described above were evaluated as described above, and the results are shown in the following Table 11. Note that these values ​​are relative values, and the initial resistance value and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 8 was used were evaluated as 100.

[0292]

[0293] From the results shown in Table 11, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where the comparative example compound is used.

[0294] Comparative Example 12-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 16 as Base) Comparative non-aqueous electrolyte solution 16 was prepared in the same manner as in the preparation of comparative non-aqueous electrolyte solution 8, except that VC and BOB were dissolved as other additives in the amounts shown in Table 12 below.

[0295] Examples 12-1 to 12-14 and Comparative Examples 12-2 to 12-8 Component (III) or a comparative compound shown in Table 12 was dissolved in the comparative nonaqueous electrolyte solution 16 to the content shown in Table 12, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0296] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 12-1 to 12-14 and the comparative nonaqueous electrolyte solutions 16 to 23 prepared as described above were evaluated as described above, and the results are shown in the following Table 12. Note that these values ​​are relative values, and the initial resistance value and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 16 was used were evaluated as 100.

[0297]

[0298] From the results shown in Table 12, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where the comparative example compound is used.

[0299] Comparative Example 13-1 (Preparation of Base Comparative Non-Aqueous Electrolyte Solution 24) Comparative non-aqueous electrolyte solution 24 was prepared in the same manner as comparative non-aqueous electrolyte solution 8, except that VC and TFOP were dissolved as other additives to the contents shown in Table 13 below.

[0300] Examples 13-1 to 13-14 and Comparative Examples 13-2 to 13-8 Component (III) or a comparative compound shown in Table 13 was dissolved in the comparative nonaqueous electrolyte solution 24 to the content shown in Table 13, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0301] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 13-1 to 13-14 and the comparative nonaqueous electrolyte solutions 24 to 31 prepared as described above were evaluated as described above, and the results are shown in the following Table 13. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 24 was used were evaluated as 100.

[0302]

[0303] From the results shown in Table 13, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where the comparative example compound is used.

[0304] Comparative Example 14-1 (Preparation of Base Comparative Non-Aqueous Electrolyte Solution 32) Comparative non-aqueous electrolyte solution 32 was prepared in the same manner as in the preparation of comparative non-aqueous electrolyte solution 8, except that VC and DFBOP were dissolved as other additives to the contents shown in Table 14 below.

[0305] Examples 14-1 to 14-14 and Comparative Examples 14-2 to 14-8 Component (III) or a comparative compound shown in Table 14 was dissolved in the comparative nonaqueous electrolyte solution 32 to give the content shown in Table 14, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0306] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 14-1 to 14-14 and the comparative nonaqueous electrolyte solutions 32 to 39 prepared as described above were evaluated as described above, and the results are shown in the following Table 14. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 32 was used were evaluated as 100.

[0307]

[0308] From the results shown in Table 14, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where the comparative example compound is used.

[0309] Comparative Example 15-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 40 as Base) Comparative non-aqueous electrolyte solution 40 was prepared in the same manner as in the preparation of comparative non-aqueous electrolyte solution 8, except that DFP, FS, and VC were dissolved as other additives to the contents shown in Table 15 below.

[0310] Examples 15-1 to 15-14 and Comparative Examples 15-2 to 15-8 Component (III) or a comparative compound shown in Table 15 was dissolved in the comparative nonaqueous electrolyte solution 40 to give the content shown in Table 15, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0311] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 15-1 to 15-14 and the comparative nonaqueous electrolyte solutions 40 to 47 prepared as described above were evaluated as described above, and the results are shown in the following Table 15. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 40 was used were evaluated as 100.

[0312]

[0313] From the results shown in Table 15, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where the comparative example compound is used.

[0314] Comparative Example 16-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 48 as Base) Comparative non-aqueous electrolyte solution 48 was prepared in the same manner as comparative non-aqueous electrolyte solution 8, except that DFP, VC, and DFPFSI were dissolved as other additives to the contents shown in Table 16 below.

[0315] Examples 16-1 to 16-14 and Comparative Examples 16-2 to 16-8 Component (III) or a comparative compound shown in Table 16 was dissolved in the comparative nonaqueous electrolyte solution 48 to give the content shown in Table 16, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0316] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 16-1 to 16-14 and the comparative nonaqueous electrolyte solutions 48 to 55 prepared as described above were evaluated as described above, and the results are shown in the following Table 16. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 48 was used were evaluated as 100.

[0317]

[0318] From the results shown in Table 16, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where the comparative example compound is used.

[0319] Comparative Example 17-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 56 as Base) Comparative non-aqueous electrolyte solution 56 was prepared in the same manner as in the preparation of comparative non-aqueous electrolyte solution 8, except that FSI was dissolved as an additional solute and DTD and VC as other additives to the contents shown in Table 17 below.

[0320] Examples 17-1 to 17-14 and Comparative Examples 17-2 to 17-8 Component (III) or a comparative compound shown in Table 17 was dissolved in the comparative nonaqueous electrolyte solution 56 to give the content shown in Table 17, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0321] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 17-1 to 17-14 and the comparative nonaqueous electrolyte solutions 56 to 63 prepared as described above were evaluated as described above, and the results are shown in the following Table 17. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 56 was used were evaluated as 100.

[0322]

[0323] From the results shown in Table 17, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing an additional solute and other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0324] Comparative Example 18-1 (Preparation of Base Comparative Non-Aqueous Electrolyte Solution 64) Comparative non-aqueous electrolyte solution 64 was prepared in the same manner as in the preparation of comparative non-aqueous electrolyte solution 8, except that FSI was dissolved as an additional solute and VC and TDUTO were dissolved as other additives to the contents shown in Table 18 below.

[0325] Examples 18-1 to 18-14 and Comparative Examples 18-2 to 18-8 Component (III) or a comparative compound shown in Table 18 was dissolved in the comparative nonaqueous electrolyte solution 64 to the content shown in Table 18, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0326] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 18-1 to 18-14 and the comparative nonaqueous electrolyte solutions 64 to 71 prepared as described above were evaluated as described above, and the results are shown in the following Table 18. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 64 was used were evaluated as 100.

[0327]

[0328] From the results shown in Table 18, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using graphite as the negative electrode active material and a nonaqueous electrolyte containing an additional solute and other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0329] Comparative Example 19-1 (Preparation of Comparative Non-aqueous Electrolyte 72 as Base) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive. They were mixed so that the volume ratio of EC:FEC:DMC:EMC was 3:0.2:3:3.8. Next, LiPF6 was added and dissolved as a solute so that the content in the non-aqueous electrolyte was 1.00 mol / L, and VC and DFOB were further dissolved as other additives so that the contents were as shown in Table 19 below, to prepare comparative non-aqueous electrolyte 72.

[0330] Examples 19-1 to 19-14 and Comparative Examples 19-2 to 19-8 Component (III) or a comparative compound shown in Table 19 was dissolved in the comparative nonaqueous electrolyte solution 72 to give the content shown in Table 19, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0331] For the nonaqueous electrolyte solutions 19-1 to 19-14 and the comparative nonaqueous electrolyte solutions 72 to 79 prepared as described above, the initial resistance and the capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in the following Table 19. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and the capacity retention rate in the cycle test when comparative nonaqueous electrolyte 72 was used are 100.

[0332]

[0333] From the results shown in Table 19, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0334] Comparative Example 20-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 80 as Base) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive. They were mixed so that the volume ratio of EC:FEC:DMC:EMC was 3:0.2:3:3.8. Next, LiPF6 was added and dissolved as a solute so that the content in the non-aqueous electrolyte solution was 1.00 mol / L, and VC and BOB were further dissolved as other additives so that the contents were as shown in Table 20 below, to prepare comparative non-aqueous electrolyte solution 80.

[0335] Examples 20-1 to 20-14 and Comparative Examples 20-2 to 20-8 Component (III) or a comparative compound shown in Table 20 was dissolved in 80% of the comparative nonaqueous electrolyte solution to give the content shown in Table 20, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0336] For the nonaqueous electrolyte solutions 20-1 to 20-14 and the comparative nonaqueous electrolyte solutions 80 to 87 prepared as described above, the initial resistance and the capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in Table 20 below. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and the capacity retention rate in the cycle test when comparative nonaqueous electrolyte 80 was used are 100.

[0337]

[0338] From the results shown in Table 20, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0339] Comparative Example 21-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 88 as Base) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive, and they were mixed so that the volume ratio thereof was EC:FEC:DMC:EMC = 3:0.2:3:3.8. Next, LiPF6 was added and dissolved as a solute so that its content in the non-aqueous electrolyte solution was 1.00 mol / L, and further VC and TFOP were each dissolved as other additives so that the contents were as shown in Table 21 below, to prepare Comparative Non-aqueous Electrolyte Solution 88.

[0340] Examples 21-1 to 21-14 and Comparative Examples 21-2 to 21-8 Component (III) or a comparative compound shown in Table 21 was dissolved in the comparative nonaqueous electrolyte solution 88 to the content shown in Table 21, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0341] For the nonaqueous electrolyte solutions 21-1 to 21-14 and comparative nonaqueous electrolyte solutions 88 to 95 prepared as described above, the initial resistance and capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in the following Table 21. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and capacity retention rate in the cycle test when comparative nonaqueous electrolyte solution 88 was used are 100.

[0342]

[0343] From the results shown in Table 21, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0344] Comparative Example 22-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 96 as Base) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive. They were mixed so that the volume ratio of EC:FEC:DMC:EMC was 3:0.2:3:3.8. Next, LiPF6 was added and dissolved as a solute so that its content in the non-aqueous electrolyte solution was 1.00 mol / L, and VC and DFBOP were further dissolved as other additives so that their contents were as shown in Table 22 below, to prepare Comparative Non-aqueous Electrolyte Solution 96.

[0345] Examples 22-1 to 22-14 and Comparative Examples 22-2 to 22-8 Component (III) or a comparative compound shown in Table 22 was dissolved in the comparative nonaqueous electrolyte solution 96 to give the content shown in Table 22, to prepare nonaqueous electrolyte solutions according to the respective examples and comparative examples.

[0346] For the nonaqueous electrolyte solutions 22-1 to 22-14 and the comparative nonaqueous electrolyte solutions 96 to 103 prepared as described above, the initial resistance and the capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in Table 22 below. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and the capacity retention rate in the cycle test when comparative nonaqueous electrolyte 96 was used are 100.

[0347]

[0348] From the results shown in Table 22, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics as well as excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0349] Comparative Example 23-1 (Preparation of Comparative Non-aqueous Electrolyte 104 as a Base) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive. They were mixed so that the volume ratio of EC:FEC:DMC:EMC was 3:0.2:3:3.8. Next, LiPF6 was added and dissolved as a solute so that the content in the non-aqueous electrolyte was 1.00 mol / L. Furthermore, DFP, VC, and FS were each dissolved as other additives so that the contents were as shown in Table 23 below, to prepare a comparative non-aqueous electrolyte 104.

[0350] Examples 23-1 to 23-14 and Comparative Examples 23-2 to 23-8 Component (III) or a comparative compound shown in Table 23 was dissolved in the comparative nonaqueous electrolyte solution 104 to the content shown in Table 23, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0351] For the nonaqueous electrolyte solutions 23-1 to 23-14 and the comparative nonaqueous electrolyte solutions 104 to 111 prepared as described above, the initial resistance and the capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in Table 23 below. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and the capacity retention rate in the cycle test when comparative nonaqueous electrolyte 104 was used are 100.

[0352]

[0353] From the results shown in Table 23, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics and overall improved initial resistance characteristics compared to the case where the comparative example compound is used.

[0354] Comparative Example 24-1 (Preparation of Comparative Non-aqueous Electrolyte 112 as a Base) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive. They were mixed so that the volume ratio of EC:FEC:DMC:EMC was 3:0.2:3:3.8. Next, LiPF6 was added and dissolved as a solute so that the content in the non-aqueous electrolyte was 1.00 mol / L. Furthermore, DFP, VC, and DFPFSI were each dissolved as other additives so that the contents were as shown in Table 24 below, to prepare a comparative non-aqueous electrolyte 112.

[0355] Examples 24-1 to 24-14 and Comparative Examples 24-2 to 24-8 Component (III) or a comparative compound shown in Table 23 was dissolved in the comparative nonaqueous electrolyte solution 112 to give the content shown in Table 24, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0356] For the nonaqueous electrolyte solutions 24-1 to 24-14 and the comparative nonaqueous electrolyte solutions 112 to 119 prepared as described above, the initial resistance and the capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in Table 24 below. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and the capacity retention rate in the cycle test when the comparative nonaqueous electrolyte solution 112 was used are 100.

[0357]

[0358] From the results shown in Table 24, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics and overall improved initial resistance characteristics compared to the case where the comparative example compound is used.

[0359] Comparative Example 25-1 (Preparation of Base Comparative Non-Aqueous Electrolyte 120) EC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive. They were mixed so that the volume ratio of EC:FEC:DMC:EMC was 3:0.2:3:3.8. Next, LiPF6 was added and dissolved as a solute so that the content in the non-aqueous electrolyte was 1.00 mol / L. Furthermore, FSI was added as an additional solute, and VC and DTD were dissolved as other additives so that the contents were as shown in Table 25 below. A comparative non-aqueous electrolyte 120 was prepared.

[0360] Examples 25-1 to 25-14 and Comparative Examples 25-2 to 25-8 Component (III) or a comparative compound shown in Table 25 was dissolved in 120 ml of the comparative nonaqueous electrolyte solution to give the content shown in Table 25, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0361] For the nonaqueous electrolyte solutions 25-1 to 25-14 and the comparative nonaqueous electrolyte solutions 120 to 127 prepared as described above, the initial resistance and the capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in Table 25. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and the capacity retention rate in the cycle test when comparative nonaqueous electrolyte 120 was used are 100.

[0362]

[0363] From the results shown in Table 25, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and using a nonaqueous electrolyte containing an additional solute and other additives exhibits excellent cycle characteristics and overall improved initial resistance characteristics compared to the case where a comparative example compound is used.

[0364] <Comparative Example 26-1> (Preparation of Comparative Non-aqueous Electrolyte 128 as Base) PC, DMC, and EMC were used as non-aqueous organic solvents, and FEC was used as other additives. They were mixed so that the volume ratio of PC:FEC:DMC:EMC was 2:0.5:4:3.5. Next, LiPF6 was added and dissolved as a solute so that the content in the non-aqueous electrolyte was 1.00 mol / L. Furthermore, LiBF4 was added as an additional solute, and VC and TDUTO were dissolved as other additives so that the contents were as shown in Table 26 below. Comparative non-aqueous electrolyte 128 was prepared.

[0365] Examples 26-1 to 26-14 and Comparative Examples 26-2 to 26-8 Component (III) or a comparative compound shown in Table 26 was dissolved in the comparative nonaqueous electrolyte solution 128 to the content shown in Table 26, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0366] For the nonaqueous electrolyte solutions 26-1 to 26-14 and the comparative nonaqueous electrolyte solutions 128 to 135 prepared as described above, the initial resistance and the capacity retention rate in the cycle test were evaluated as described above in nonaqueous electrolyte batteries using Si-graphite as the negative electrode active material, and the results are shown in Table 26 below. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and the capacity retention rate in the cycle test when comparative nonaqueous electrolyte 128 was used are 100.

[0367]

[0368] From the results shown in Table 26, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using Si-graphite as the negative electrode active material and using a nonaqueous electrolyte containing an additional solute and other additives exhibits excellent cycle characteristics and overall improved initial resistance characteristics compared to the case where a comparative example compound is used.

[0369] (Sodium ion battery positive electrode: NaNi 0.5 Ti 0.3 Mn 0.2 Preparation of O2 cathode) NaNi as the cathode active material 0.5 Ti 0.3 Mn 0.2 A slurry solution was prepared by mixing 90% by mass of O2, 5% by mass of acetylene black as a conductive agent, and 5% by mass of PVDF as a binder, and then adding NMP as a solvent in an amount of 50% by mass relative to the total mass of the positive electrode active material, conductive agent, and binder. This slurry solution was applied to both sides of an aluminum foil (A1085) serving as a positive electrode current collector, dried at 150°C for 12 hours, and then punched out to 4 cm x 5 cm to obtain a test NaNi foil having a positive electrode active material layer formed on the current collector. 0.5 Ti 0.3 Mn 0.2 An O2 positive electrode was obtained.

[0370] (Preparation of Hard Carbon Negative Electrode) 90% by mass of hard carbon powder (Carbotron P, manufactured by Kureha Corporation) and 10% by mass of PVDF as a binder were mixed, and NMP as a solvent was further added in an amount of 50% by mass relative to the total mass of the negative electrode active material and the binder to prepare a slurry solution. This slurry solution was applied to an aluminum foil negative electrode current collector, dried at 150°C for 12 hours, and then punched out to 4.5 cm x 5.5 cm to obtain a test hard carbon negative electrode having a negative electrode active material layer formed on the current collector.

[0371] (Preparation of non-aqueous electrolyte battery) The above-mentioned NaNi 0.5 Ti 0.3 Mn 0.2 After a terminal was welded to the O2 positive electrode, the positive electrode was sandwiched between two polyethylene separators (5 cm x 6 cm), and the outer surface of the separator was sandwiched between two hard carbon negative electrodes, each of which had a terminal welded to it, so that the negative electrode active material surface faced the positive electrode active material surface. These components were then placed in an aluminum-laminated bag with an opening on one side. A nonaqueous electrolyte solution, which will be described later, was vacuum-injected into the bag, and the opening was then heat-sealed to produce aluminum-laminated nonaqueous electrolyte batteries according to the examples and comparative examples shown in the tables below.

[0372] [Evaluation Conditions] (Initial Charge / Discharge) Each of the nonaqueous electrolyte batteries (cells) prepared as described above was left to stand for 12 hours (impregnation time: 12 hours) at an ambient temperature of 25° C., and then conditioned under the following conditions at an ambient temperature of 25° C. That is, as the initial charge / discharge, the battery was charged at a constant current / constant voltage of 0.1 C rate (9 mA) to an upper charge voltage of 4.1 V, and discharged at a constant current of 0.2 C rate to a discharge cut-off voltage of 1.5 V. Thereafter, the battery was charged at a constant current / constant voltage of 0.2 C rate to an upper charge voltage of 4.1 V, and discharged at a constant current of 0.2 C rate to a discharge cut-off voltage of 1.5 V. This charge / discharge cycle was repeated three times.

[0373] (Initial Resistance Measurement) The cell that had been subjected to the above conditioning was charged to 4.3 V at 25° C. and a rate of 0.2 C, and then impedance measurement was carried out in an environment of −20° C. to measure the resistance value.

[0374] (Cycle Test) A charge / discharge test was carried out at an ambient temperature of 25°C on the cells whose initial resistances had been measured, and the cycle characteristics were evaluated. A charge / discharge cycle was repeated at a current value of 90 mA using a constant current / constant voltage method, with an upper charge voltage limit of 4.1 V and a lower discharge voltage limit of 1.5 V. The discharge capacity retention rate at the 400th cycle in the charge / discharge test at an ambient temperature of 25°C was calculated as follows to evaluate the degree of cell deterioration. The "discharge capacity retention rate after cycling," expressed as the discharge capacity retention rate at the 400th cycle, was calculated using the following formula. The discharge capacity at the first cycle in the charge / discharge test at an ambient temperature of 25°C was defined as the initial discharge capacity. Discharge capacity retention rate after cycling (%) = (discharge capacity at the 400th cycle / initial discharge capacity) x 100

[0375] Comparative Example 27-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 136 as Base) EC, PC, and EMC were used as non-aqueous organic solvents, and FEC was used as another additive, and they were mixed so that the volume ratio of EC:PC:FEC:EMC was 1:2:0.2:6. Next, NaPF was added as a solute and dissolved so that the content in the non-aqueous electrolyte solution was 1.00 mol / L, thereby preparing Comparative Non-aqueous Electrolyte Solution 136.

[0376] Examples 27-1 to 27-14 and Comparative Examples 27-2 to 27-8 Component (III) or a comparative compound shown in Table 27 was dissolved in the comparative nonaqueous electrolyte solution 136 to give the content shown in Table 27, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0377] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 27-1 to 27-14 and the comparative nonaqueous electrolyte solutions 136 to 143 prepared as described above were evaluated as described above, and the results are shown in the following Table 27. Note that these values ​​are relative values, and are evaluated assuming that the initial resistance and capacity retention rate in the cycle test for the comparative nonaqueous electrolyte solution 136 are 100.

[0378]

[0379] From the results shown in Table 27, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using hard carbon as a negative electrode active material exhibits excellent cycle characteristics and excellent initial resistance characteristics compared to the case where the comparative example compound is used.

[0380] Comparative Example 28-1 (Preparation of Comparative Non-aqueous Electrolyte Solution 144 as Base) A solvent in which PC, DMC, and EMC were mixed at a volume ratio of PC:DMC:EMC=3:4:3 was used as the non-aqueous organic solvent, and NaPF was dissolved as a solute in the solvent so that its content in the non-aqueous electrolyte solution was 1.00 mol / L. Furthermore, VC and Na-DFOB shown below were dissolved as other additives so that their contents were as shown in Table 28 below, to prepare comparative non-aqueous electrolyte solution 144.

[0381]

[0382] Examples 28-1 to 28-14 and Comparative Examples 28-2 to 28-8 Component (III) or a comparative compound shown in Table 28 was dissolved in the comparative nonaqueous electrolyte solution 144 to give the content shown in Table 28, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0383] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 28-1 to 28-14 and the comparative nonaqueous electrolyte solutions 144 to 151 prepared as described above were evaluated as described above, and the results are shown in the following Table 28. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 144 was used were evaluated as 100.

[0384]

[0385] From the results shown in Table 28, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using hard carbon as a negative electrode active material and a nonaqueous electrolyte containing other additives exhibits superior cycle characteristics and superior initial resistance characteristics compared to the case where a comparative example compound is used.

[0386] Comparative Example 29-1 (Preparation of Base Comparative Non-Aqueous Electrolyte Solution 152) Comparative non-aqueous electrolyte solution 152 was prepared in the same manner as in Comparative Example 28-1, except that, as an additive, instead of 1.0 mass % Na-DFOB, Na-TFOP shown below was dissolved to the content shown in Table 29 below.

[0387]

[0388] Examples 29-1 to 29-14 and Comparative Examples 29-2 to 29-8 Component (III) or a comparative compound shown in Table 29 was dissolved in the comparative nonaqueous electrolyte solution 152 to give the content shown in Table 29, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0389] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 29-1 to 29-14 and the comparative nonaqueous electrolyte solutions 152 to 159 prepared as described above were evaluated as described above, and the results are shown in the following Table 29. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 152 was used were evaluated as 100.

[0390]

[0391] From the results shown in Table 29, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using hard carbon as a negative electrode active material and a nonaqueous electrolyte containing other additives exhibits superior cycle characteristics and superior initial resistance characteristics compared to the case where a comparative example compound is used.

[0392] Comparative Example 30-1 (Preparation of Base Comparative Non-Aqueous Electrolyte Solution 160) Comparative non-aqueous electrolyte solution 160 was prepared in the same manner as in Comparative Example 28-1, except that, as an additive, instead of 1.0 mass % Na-DFOB, Na-DFBOP shown below was dissolved to the content shown in Table 30 below.

[0393]

[0394] Examples 30-1 to 30-14 and Comparative Examples 30-2 to 30-8 Component (III) or a comparative compound shown in Table 30 was dissolved in 160 ml of the comparative nonaqueous electrolyte solution to give the content shown in Table 30, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0395] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 30-1 to 30-14 and the comparative nonaqueous electrolyte solutions 160 to 167 prepared as described above were evaluated as described above, and the results are shown in the following Table 30. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 160 was used were evaluated as 100.

[0396]

[0397] From the results shown in Table 30, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using hard carbon as a negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics and excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0398] Comparative Example 31-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 168 as Base) Comparative non-aqueous electrolyte solution 168 was prepared in the same manner as in Comparative Example 28-1, except that, as an additive, Na-DFP represented by the following formula was dissolved in place of 1.0 mass% Na-DFOB so as to obtain the content shown in Table 31 below.

[0399]

[0400] Examples 31-1 to 31-14 and Comparative Examples 31-2 to 31-8 Component (III) or a comparative compound shown in Table 31 was dissolved in 168 of the comparative nonaqueous electrolyte solution to give the content shown in Table 31, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0401] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 31-1 to 31-14 and the comparative nonaqueous electrolyte solutions 168 to 175 prepared as described above were evaluated as described above, and the results are shown in the following Table 31. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 168 was used were evaluated as 100.

[0402]

[0403] From the results shown in Table 31, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using hard carbon as a negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics and excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0404] Comparative Example 32-1 (Preparation of Comparative Non-Aqueous Electrolyte Solution 176 as Base) Comparative non-aqueous electrolyte solution 176 was prepared in the same manner as in Comparative Example 28-1, except that, as an additive, Na-FS represented by the following formula was dissolved in place of 1.0 mass % Na-DFOB so as to obtain the content shown in Table 32 below.

[0405]

[0406] Examples 32-1 to 32-14 and Comparative Examples 32-2 to 32-8 Component (III) or a comparative compound shown in Table 32 was dissolved in the comparative nonaqueous electrolyte solution 176 to give the content shown in Table 32, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0407] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 32-1 to 32-14 and the comparative nonaqueous electrolyte solutions 176 to 183 prepared as described above were evaluated as described above, and the results are shown in the following Table 32. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 176 was used were evaluated as 100.

[0408]

[0409] From the results shown in Table 32, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using hard carbon as a negative electrode active material and a nonaqueous electrolyte containing other additives exhibits excellent cycle characteristics and excellent initial resistance characteristics compared to the case where a comparative example compound is used.

[0410] Comparative Example 33-1 (Preparation of Base Comparative Non-Aqueous Electrolyte Solution 184) Comparative non-aqueous electrolyte solution 184 was prepared in the same manner as in Comparative Example 28-1, except that, as an additive, DTD was dissolved in place of 1.0 mass% Na-DFOB to achieve the content shown in Table 33 below.

[0411] Examples 33-1 to 33-14 and Comparative Examples 33-2 to 33-8 Component (III) or a comparative compound shown in Table 33 was dissolved in the comparative nonaqueous electrolyte solution 184 to give the content shown in Table 33, to prepare nonaqueous electrolyte solutions according to the respective Examples and Comparative Examples.

[0412] The initial resistance and capacity retention rate in the cycle test for the nonaqueous electrolyte solutions 33-1 to 33-14 and the comparative nonaqueous electrolyte solutions 184 to 191 prepared as described above were evaluated as described above, and the results are shown in the following Table 33. Note that these values ​​are relative values, and the initial resistance and capacity retention rate in the cycle test for the case where comparative nonaqueous electrolyte solution 184 was used were evaluated as 100.

[0413]

[0414] From the results shown in Table 33, it can be seen that by containing component (III) of the present disclosure, a nonaqueous electrolyte battery using hard carbon as a negative electrode active material and a nonaqueous electrolyte containing other additives exhibits superior cycle characteristics and superior initial resistance characteristics compared to the case where a comparative example compound is used.

Claims

1. A non-aqueous electrolyte solution comprising: (I) a solute; (II) a non-aqueous organic solvent; and (III) at least one selected from the group consisting of a compound represented by the following general formula (1), a compound represented by the general formula (2), a compound represented by the general formula (3), a compound represented by the general formula (4), a compound represented by the general formula (5), a compound represented by the general formula (6), a compound represented by the general formula (7), and a compound represented by the general formula (8). In the general formula (1), m represents an integer of 0 or 1. a is a hydrogen atom or (M A+ ) a where M A+ represents a metal cation or an onium cation, A represents the valence of the cation, and a represents a number such that A×a=1. 1 is -S(=O)2R a , or -P(=O)(R b ) (R c ) represents R a , R b and R c are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M2 B+ ) b where M B+ represents a proton, a metal cation, or an onium cation, B represents the valence of the cation, and b represents a number such that B×b=1. b and R c may be taken together with each other to form a 5- or 6-membered ring together with the phosphorus atom. 2 and R 3 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 2 and R 3 may be united to form a carbonyl group. [In general formula (2), R 4 is a halogen atom, -(O) x1 -S(=O)2R d , -(O) y1 -P(=O)(R e ) (R f ), or -O - (M3 C+ ) c where M3 C+ represents a proton, a metal cation or an onium cation, C represents the valence of the cation, c represents a number such that C×c=1, and x1 and y1 each represent an integer of 0 or 1. d , R e and R f are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M4 D+ ) d where M4 D+ represents a proton, a metal cation or an onium cation, D represents the valence of the cation, and d represents a number such that D×d=1. 5 and R 6 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 5 and R 6 may be united to form a carbonyl group. [In general formula (3), M b is a hydrogen atom or (M E+ ) e where M5 E+ represents a metal cation or an onium cation, E represents the valence of the cation, and e represents a number such that E×e=1. 7 and R 7 each ' is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryl group having 6 to 1 a hydrocarbon group selected from an aryloxy group having 0 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group), -S(=O)R g , or -P(=O)(R h ) (R i ) represents R g , R h and R i are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M6 F+ ) f where M6 F+ represents a proton, a metal cation or an onium cation, F represents the valence of the cation, and f represents a number such that F×f=1. 8 and R 9 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 8 and R 9 may be united to form a carbonyl group. [In general formula (4), R 10 , R 11 , R 12 and R 13 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 10 and R 11 Or R 12 and R 13 may each independently and together form a carbonyl group. In the general formula (5), n represents an integer of 0 or 1. c is a hydrogen atom or (M G+ ) g where M7 G+ represents a metal cation or an onium cation, G represents the valence of the cation, and g represents a number such that G×g=1. 14 is -S(=O)2R j , or -P(=O)(R k ) (R l ), where R j , R k and R l are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M8 H+ ) h where M8 H+ represents a proton, a metal cation or an onium cation, H represents the valence of the cation, and h represents a number such that H×h=1. 15 and R 16 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 15 and R 16 may be united to form a carbonyl group. [In general formula (6), R 17 is a halogen atom, -(O) x2 -S(=O)2R m , -(O) y2 -P(=O)(R n ) (R o ), or -O - (M9 I+ ) i where M9 I+ represents a proton, a metal cation or an onium cation, I represents the valence of the cation, and i represents a number such that I×i=1. x2 and y2 represent integers of 0 or 1. m , R n and R o are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M 10 J+ ) j where M 10 J+ represents a proton, a metal cation or an onium cation, J represents the valence of the cation, and j represents a number such that J×j=1. 18 and R 19 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 18 and R 19 may be united to form a carbonyl group. [In general formula (7), M d is a hydrogen atom or (M 11 K+ ) k where M 11 K+ represents a metal cation or an onium cation, K represents the valence of the cation, and k represents a number such that K×k=1. 20 and R 20’ each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydrocarbon group selected from an aryloxy group represented by the formula (I), a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group), -S(=O)R p , or -P(=O)(R q ) (R r ) represents R p , R q and R r are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M 12 L+ ) l where M 12 L+ represents a proton, a metal cation or an onium cation, L represents the valence of the cation, and l represents a number such that L×l=1. 21 and R 22 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 21 and R 22 may be united to form a carbonyl group. [In general formula (8), R 23 , R 24 , R 25 and R 26 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 23 and R 24 , or R 25 and R 26 may each independently and together form a carbonyl group.

2. The nonaqueous electrolyte according to claim 1, wherein the concentration of said (III) is 0.009 to 11.5 mass % based on the total amount of said nonaqueous electrolyte.

3. The nonaqueous electrolyte solution according to claim 1, wherein the (III) is at least one selected from the group consisting of a compound represented by general formula (1), a compound represented by general formula (2), a compound represented by general formula (3), a compound represented by general formula (4), a compound represented by general formula (5), a compound represented by general formula (6), and a compound represented by general formula (7).

4. The nonaqueous electrolyte solution according to claim 1, wherein the (III) is at least one selected from the group consisting of a compound represented by general formula (1), a compound represented by general formula (2), a compound represented by general formula (3), and a compound represented by general formula (4).

5. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (1) is at least one selected from the following compounds:

6. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (2) is at least one selected from the following compounds:

7. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (3) is at least one selected from the following compounds:

8. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (4) is at least one selected from the following compounds:

9. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (5) is at least one selected from the following compounds:

10. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (6) is at least one selected from the following compounds:

11. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (7) is at least one selected from the following compounds:

12. The nonaqueous electrolyte according to claim 1, wherein the compound represented by the general formula (8) is at least one selected from the following compounds:

13. The nonaqueous electrolyte according to claim 1, wherein (I) is at least one selected from the group consisting of LiPF6, LiBF4, LiSbF6, LiAsF6, LiClO4, LiN(SO2F)2, LiAlO2, LiAlCl4, LiCl, and LiI, or at least one selected from the group consisting of NaPF6, NaBF4, NaSbF6, NaAsF6, NaClO4, NaN(SO2F)2, NaAlO2, NaAlCl4, NaCl, and NaI.

14. The nonaqueous electrolyte according to claim 1, wherein the (II) 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.

15. The nonaqueous electrolyte according to claim 14, wherein the cyclic ester comprises a cyclic carbonate.

16. The nonaqueous electrolyte according to claim 15, wherein the cyclic carbonate comprises at least one selected from the group consisting of ethylene carbonate and propylene carbonate.

17. The nonaqueous electrolyte according to claim 14, wherein the chain ester comprises a chain carbonate.

18. The nonaqueous electrolyte according to claim 17, wherein the chain carbonate comprises at least one selected from the group consisting of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, and methyl propyl carbonate.

19. In addition, cyclohexylbenzene, cyclohexylfluorobenzene, biphenyl, 2-fluorobiphenyl, t-butylbenzene, t-amylbenzene, 2-fluorotoluene, fluorobenzene, vinylene carbonate, vinylene carbonate oligomers (having a number average molecular weight of 170 to 5000 calculated as polystyrene), vinylethylene carbonate, difluoroanisole, fluoroethylene carbonate, 1,6-diisocyanatohexane, ethynylethylene carbonate, trans-difluoroethylene carbonate, methylpropargyl carbonate, sultone, ethyl propargyl carbonate, dipropargyl carbonate, maleic anhydride, succinic anhydride, 1,3-propane sultone, 1,3-propene sultone, 1,4-butane sultone, dimethylvinylene carbonate, 1,3,2-dioxathiolane-2,2-dioxide, 4-propyl-1,3,2-dioxathiolane-2,2-dioxide, methylenemethane disulfonate, dimethylmethane disulfonate, trimethylenemethane disulfonate, methyl methanesulfonate, methanesulfonyl fluoride, ethenesulfonyl fluoride, diphenyl ether Phenyl fluorophosphate, 1,2-ethanedisulfonic anhydride, tris(trimethylsilyl)borate, succinonitrile, (ethoxy)pentafluorocyclotriphosphazene, tetrafluoro(picolinato)phosphate, difluoro(picolinato)borate, 1,3-dimethyl-1,3-divinyl-1,3-di(1,1,1,3,3,3-hexafluoroisopropyl)disiloxane, lithium difluorophosphate, sodium difluorophosphate, lithium fluorosulfate, sodium fluorosulfate, lithium trifluoromethanesulfonate, trifluoro sodium fluoromethanesulfonate, lithium nonafluorobutanesulfonate, sodium nonafluorobutanesulfonate, lithium difluorobis(oxalato)phosphate, sodium difluorobis(oxalato)phosphate, lithium difluorooxalatoborate, sodium difluorooxalatoborate, lithium bis(oxalato)borate, sodium bis(oxalato)borate, lithium tetrafluorooxalatophosphate, sodium tetrafluorooxalatophosphate, lithium tris(oxalato)phosphate, sodium tris(oxalato)phosphate,Lithium difluoro(malonato)borate, sodium difluoro(malonato)borate, lithium tetrafluoro(malonato)phosphate, sodium tetrafluoro(malonato)phosphate, lithium monofluorophosphate, sodium monofluorophosphate, lithium bis(difluorophosphoryl)imide, sodium bis(difluorophosphoryl)imide, lithium (difluorophosphoryl)(fluorosulfonyl)imide, sodium (difluorophosphoryl)(fluorosulfonyl)imide, lithium bis(trifluoromethanesulfonyl)imide, sodium bis(trifluoromethanesulfonyl)imide, lithium bis(pentafluoroethanesulfonyl)imide, sodium bis(pentafluoroethanesulfonyl)imide, lithium (trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)imide, lithium (trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)imide, (trifluoromethanesulfonyl)(pentafluoroethanesulfonyl)imide The non-aqueous electrolyte according to claim 1, which contains at least one selected from the group consisting of sodium (fluoroethanesulfonyl)imide, sodium (trifluoromethanesulfonyl)(fluorosulfonyl)imide, lithium (trifluoromethanesulfonyl)(fluorosulfonyl)imide, sodium (trifluoromethanesulfonyl)(fluorosulfonyl)imide, lithium (pentafluoroethanesulfonyl)(fluorosulfonyl)imide, sodium (pentafluoroethanesulfonyl)(fluorosulfonyl)imide, lithium tris(trifluoromethanesulfonyl)methide, sodium tris(trifluoromethanesulfonyl)methide, lithium acrylate, sodium acrylate, lithium methacrylate, sodium methacrylate, lithium methyl sulfate, sodium methyl sulfate, lithium ethyl sulfate, sodium ethyl sulfate, lithium nitrate, lithium nitrite, sodium nitrite, and sodium nitrite.

20. The nonaqueous electrolyte according to claim 1, further comprising a compound represented by the following general formula (9): [In general formula (9), R 27 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, and an oxygen atom may be contained between any carbon atom-carbon atom bond in the alkyl group. In addition, any hydrogen atom in the alkyl group may be substituted with a fluorine atom.

21. The compound represented by the general formula (9) is the following compound: The nonaqueous electrolyte according to claim 20, which is at least one selected from the group consisting of:

22. The nonaqueous electrolyte according to claim 1, further comprising a compound represented by the following general formula (10): [In general formula (10), R 28 ~R 31 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, or an aryl group; and X represents an oxygen atom, a sulfur atom, or an SO2 group.

23. The nonaqueous electrolyte according to claim 22, wherein the compound of formula (10) is a compound represented by the following formula:

24. A nonaqueous electrolyte battery comprising at least a positive electrode, a negative electrode, a separator, and the nonaqueous electrolyte according to any one of claims 1 to 23.

25. A compound represented by any one of the following general formulas (1) to (8): In the general formula (1), m represents an integer of 0 or 1. a is a hydrogen atom or (M A+ ) a where M A+ represents a metal cation or an onium cation, A represents the valence of the cation, and a represents a number such that A×a=1. 1 is -S(=O)2R a , or -P(=O)(R b ) (R c ) represents R a , R b and R c are each independently a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M2 B+ ) b where M B+ represents a proton, a metal cation, or an onium cation, B represents the valence of the cation, and b represents a number such that B×b=1. b and R c may be taken together with each other to form a 5- or 6-membered ring together with the phosphorus atom. 2 and R 3 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 2 and R 3 may be united to form a carbonyl group. [In general formula (2), R 4 is a halogen atom, -(O) x1 -S(=O)2R d , -(O) y1 -P(=O)(R e ) (R f ), or -O - (M3 C+ ) c where M3 C+ represents a proton, a metal cation or an onium cation, C represents the valence of the cation, c represents a number such that C×c=1, and x1 and y1 each represent an integer of 0 or 1. d , R e and R f are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M4 D+ ) d where M4 D+ represents a proton, a metal cation or an onium cation, D represents the valence of the cation, and d represents a number such that D×d=1. 5 and R 6 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 5 and R 6 may be united to form a carbonyl group. [In general formula (3), M b is a hydrogen atom or (M E+ ) e where M5 E+ represents a metal cation or an onium cation, E represents the valence of the cation, and e represents a number such that E×e=1. 7 and R 7 each ' is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryl group having 6 to 1 a hydrocarbon group selected from an aryloxy group having 0 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group), -S(=O)R g , or -P(=O)(R h ) (R i ) represents R g , R h and R i are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M6 F+ ) f where M6 F+ represents a proton, a metal cation or an onium cation, F represents the valence of the cation, and f represents a number such that F×f=1. 8 and R 9 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 8 and R 9 may be united to form a carbonyl group. [In general formula (4), R 10 , R 11 , R 12 and R 13 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 10 and R 11 Or R 12 and R 13 may each independently and together form a carbonyl group. In the general formula (5), n represents an integer of 0 or 1. c is a hydrogen atom or (M G+ ) g where M7 G+ represents a metal cation or an onium cation, G represents the valence of the cation, and g represents a number such that G×g=1. 14 is -S(=O)2R j , or -P(=O)(R k ) (R l ), where R j , R k and R l are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M8 H+ ) h where M8 H+ represents a proton, a metal cation or an onium cation, H represents the valence of the cation, and h represents a number such that H×h=1. 15 and R 16 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 15 and R 16 may be united to form a carbonyl group. [In general formula (6), R 17 is a halogen atom, -(O) x2 -S(=O)2R m , -(O) y2 -P(=O)(R n ) (R o ), or -O - (M9 I+ ) i where M9 I+ represents a proton, a metal cation or an onium cation, I represents the valence of the cation, and i represents a number such that I×i=1. x2 and y2 represent integers of 0 or 1. m , R n and R o are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M 10 J+ ) j where M 10 J+ represents a proton, a metal cation or an onium cation, J represents the valence of the cation, and j represents a number such that J×j=1. 18 and R 19 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 18 and R 19 may be united to form a carbonyl group. [In general formula (7), M d is a hydrogen atom or (M 11 K+ ) k where M 11 K+ represents a metal cation or an onium cation, K represents the valence of the cation, and k represents a number such that K×k=1. 20 and R 20’ each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydrocarbon group selected from an aryloxy group represented by the formula (I), a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group), -S(=O)R p , or -P(=O)(R q ) (R r ) represents R p , R q and R r are each independently a hydrocarbon group selected from a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkoxy group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, a cycloalkenyloxy group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 10 carbon atoms, and a heteroaryloxy group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms of the hydrocarbon group may each be independently substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms of the hydrocarbon group), or -O - (M 12 L+ ) l where M 12 L+ represents a proton, a metal cation or an onium cation, L represents the valence of the cation, and l represents a number such that L×l=1. 21 and R 22 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 21 and R 22 may be united to form a carbonyl group. [In general formula (8), R 23 , R 24 , R 25 and R 26 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group selected from an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a heteroaryl group having 6 to 10 carbon atoms (a part or all of the hydrogen atoms in the hydrocarbon group may each independently be substituted with a halogen atom, a cyano group, an isocyano group, a cycloalkyl group, or an aryl group, and a carbonyl group, an oxygen atom, a sulfur atom, or a nitrogen atom may be present between any carbon-carbon atoms in the hydrocarbon group). 23 and R 24 , or R 25 and R 26 may each independently and together form a carbonyl group.

26. The compound according to claim 25, wherein the compound represented by the general formula (1) is selected from the following compounds:

27. The compound according to claim 25, wherein the compound represented by the general formula (2) is selected from the following compounds:

28. The compound according to claim 25, wherein the compound represented by the general formula (3) is selected from the following compounds:

29. The compound according to claim 25, wherein the compound represented by the general formula (4) is selected from the following compounds:

30. The compound according to claim 25, wherein the compound represented by the general formula (5) is selected from the following compounds:

31. The compound according to claim 25, wherein the compound represented by the general formula (6) is selected from the following compounds:

32. The compound according to claim 25, wherein the compound represented by the general formula (7) is selected from the following compounds:

33. The compound according to claim 25, wherein the compound represented by the general formula (8) is selected from the following compounds:

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