JP2010215512A - Ionic liquid, method for producing ionic liquid, electrolyte and lithium secondary battery - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new ionic liquid for obtaining an electrolyte that has excellent electroconductivity, particularly electroconductivity at a low temperature, is excellently safe and is therefore useful for a lithium secondary battery, and to provide an electrolyte comprising the same and a lithium secondary battery. <P>SOLUTION: The ionic liquid comprises a β-carbonyl-enolate anion. The electrolyte comprises the ionic liquid (A) comprising the β-carbonyl-enolate anion and a salt of an electrolyte (B). The lithium secondary battery comprises the same. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a novel ionic liquid and a method for producing the same, and further, an ionic liquid useful for a lithium secondary battery excellent in electrochemical properties such as conductivity and excellent in safety, an ionic liquid electrolyte, and The present invention relates to a lithium secondary battery using the same.

  In recent years, lithium secondary batteries have been widely used in information electronic devices such as notebook computers, mobile phones, and PDAs, and the demand for more comfortable portability has led to rapid reductions in size, thickness, weight, and performance of batteries. Is going on. In addition, the application of lithium secondary batteries is also being studied in electric vehicles that are expected as next-generation vehicles, and further miniaturization, weight reduction, and higher performance are required.

  On the other hand, the safety of current lithium secondary batteries has become a problem, such as the firing and explosion of information electronic equipment. Since current lithium secondary batteries use a flammable and volatile organic solvent as an electrolyte, there is always a risk of ignition or explosion. These risks increased as the capacity of the battery increased, and hindered the spread of electric vehicles.

  Therefore, lithium secondary batteries using a flame-retardant and low-volatile ionic liquid as an electrolyte have been studied. The ionic liquid referred to here is a salt composed of a cation and an anion, and is a compound having a melting point near room temperature or lower.

  As an ionic liquid for electrolyte, for example, an ionic liquid composed of a specific sulfonium cation and a specific imide anion has been proposed (see, for example, Patent Document 1).

JP 2004-203763 A

  However, in the ionic liquid of the above disclosed technology, the melting point and the electrical conductivity are still not sufficient as an electrolyte for a lithium secondary battery. In particular, next-generation batteries for electric vehicles and the like need to operate even at low temperatures. For example, they do not freeze at −30 ° C., and must maintain a conductivity of 0.001 mS / cm or higher at −30 ° C. Further improvements are required to meet the required performance.

  Therefore, in the present invention, a novel ionic liquid useful for a lithium secondary battery having excellent electrochemical characteristics such as conductivity and safety and an electrolyte, and further a lithium secondary battery are provided. It is intended to provide.

  However, as a result of intensive studies in view of such circumstances, the present inventors have achieved excellent electrochemical properties and safety by using an ionic liquid having a β-carbonylenolate-based anion, and in particular, conductivity at low temperatures. The inventors have found that an excellent electrolyte can be obtained and completed the present invention.

  The reason why the electrochemical characteristics are improved by using an ionic liquid composed of a β-carbonylenolate anion is not clear, but it is presumed that the chemical structure of the anion greatly contributes to the lithium ion conductivity. That is, the size and polarizability of such anions are thought to improve conductivity because they help the movement of lithium ions in the electrolyte.

  The ionic liquid of the present invention is useful as an electrolyte material, and an electrolyte obtained therefrom has excellent electrochemical characteristics such as conductivity and safety, and particularly has an effect of excellent conductivity at low temperatures. .

The present invention is described in detail below.
In addition, the ionic liquid in this invention represents the ionic substance which consists of a cation and an anion which hold | maintains a liquid at the fixed temperature of the range of 0-150 degreeC.

  The ionic liquid of the present invention is an ionic liquid having a β-carbonyl enolate anion represented by the following general formula (1) or (2).

（ここで、Ｒ₁、Ｒ₂は同じでも異なっても良く、ハロゲンやエーテル結合を含んでも良い炭素数１〜１０のアルキル基、もしくは、ハロゲンやエーテル結合を含んでも良い炭素数１〜１０のアルコキシ基である。Ｒ₃は、フェニル基、ハロゲンやエーテル結合を含んでも良い炭素数１〜１０のアルキル基、もしくはハロゲンやエーテル結合を含んでも良い炭素数１〜１０のアルコキシ基である。）

(Here, R ₁ and R ₂ may be the same or different, and an alkyl group having 1 to 10 carbon atoms which may contain a halogen or an ether bond, or a C 1-10 carbon atom which may contain a halogen or an ether bond. R ₃ is a phenyl group, an alkyl group having 1 to 10 carbon atoms which may contain a halogen or an ether bond, or an alkoxy group having 1 to 10 carbon atoms which may contain a halogen or an ether bond.

（ここでＲ₁₂は、ハロゲンやエーテル結合を含んでも良い炭素数１〜１０のアルキレン基である。Ｒ₄は、フェニル基、ハロゲンやエーテル結合を含んでも良い炭素数１〜１０のアルキル基、もしくはハロゲンやエーテル結合を含んでも良い炭素数１〜１０のアルコキシ基である。）

(Wherein R ₁₂ is an alkylene group having 1 to 10 carbon atoms which may contain a halogen or an ether bond. R ₄ is a phenyl group, an alkyl group having 1 to 10 carbon atoms which may contain a halogen or an ether bond, Or it is a C1-C10 alkoxy group which may contain a halogen or an ether bond.)

Examples of the β-carbonyl enolate anion in the present invention include 2,4-pentanedionate (R ₁ : CH ₃ , R ₂ : CH ₃ ), 3-methyl-2,4-pentanedionate, 3-ethyl. -2,4-pentanedionate, 3-propyl-2,4-pentanedionate, 3-methoxy-2,4-pentanedionate, 3-ethoxy-2,4-pentanedionate, 3-propoxy-2 , 4-pentanedionate, 3-phenyl-2,4-pentanedionate, 2,4-hexanedionate (R ₁ : CH ₃ , R ₂ : CH ₂ CH ₃ ), 3-methyl-2,4- Hexanedionate, 3-ethyl-2,4-hexanedionate, 3-propyl-2,4-hexanedionate, 3-methoxy-2,4-hexanedionate, 3-ethoxy-2,4- Hexane Geo diisocyanate, 3-propoxy-2,4-hexanedionato diisocyanate, 3-phenyl-2,4-hexanedionato diisocyanate,

2,4-heptane dionate (R ₁ : CH ₃ , R ₂ : CH ₂ CH ₂ CH ₃ ), 3,5-heptane dionate (R ₁ : CH ₂ CH ₃ , R ₂ : CH ₂ CH ₃ ), 2,4-octane dionate (R ₁ : CH ₃ , R ₂ : CH ₂ CH ₂ CH ₂ CH ₃ ), 3,5-octane dionate (R ₁ : CH ₂ CH ₃ , R ₂ : CH ₂ CH ₂ CH ₃ ), 1,3-cyclobutane dionate (R ₁₂ : CH ₂ ), 1,3-cyclopentane dionate (R ₁₂ : CH ₂ CH ₂ ), 1,3-cyclohexane dionate (R ₁₂ : CH ₂ CH ₂ CH ₂ ), 1,3-cycloheptane dionate (R ₁₂ : CH ₂ CH ₂ CH ₂ CH ₂ ), 1,3-cyclooctane dionate (R ₁₂ : CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ ), 1-fluoro-2,4-pentanedionate _{(R 1: CH 2 F,} R 2 CH _3), 1,1-difluoro-2,4-pentanedionate _{(R 1: CHF 2, R} 2: CH 3), 1,1,1- trifluoro-2,4-pentanedionate (R ₁ : CF ₃ , R ₂ : CH ₃ ), 1,1,1,5-tetrafluoro-2,4-pentanedionate (R ₁ : CF ₃ , R ₂ : CH ₂ F), 1,1,1, 5,5-pentafluoro-2,4-pentanedionate (R ₁ : CF ₃ , R ₂ : CHF ₂ ), 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate (R ₁ : CF ₃ , R ₂ : CF ₃ ),

1-fluoro-2,4-hexane dionate (R ₁ : CH ₂ F, R ₂ : CH ₂ CH ₃ ), 1,1-difluoro-2,4-hexane dionate (R ₁ : CHF ₂ , R ₂ : CH ₂ CH ₃ ), 1,1,1-trifluoro-2,4-hexane dionate (R ₁ : CF ₃ , R ₂ : CH ₂ CH ₃ ), 6-fluoro-2,4-hexane dionate (R ₁ : CH ₃ , R ₂ : CH ₂ CH ₂ F), 6,6-difluoro-2,4-hexane dionate (R ₁ : CH ₃ , R ₂ : CH ₂ CHF ₂ ), 6, 6, 6-trifluoro-2,4-hexane dionate (R ₁ : CH ₃ , R ₂ : CH ₂ CF ₃ ), 1,6,6,6-tetrafluoro-2,4-hexane dionate (R ₁ : _{CH 2 F, R 2: CH} 2 CF 3), 1,1,6,6,6- pentafluoro-2,4-hexanediol Over preparative _{(R 1: CHF 2, R} 2: CH 2 CF 3), 1,1,1,6,6,6- hexafluoro-2,4-hexanedionato Inert _{(R 1: CF 3, R} 2: CH ₂ CF ₃ ), 5,5,6,6,6-pentafluoro-2,4-hexanedionate (R ₁ : CH ₃ , R ₂ : CF ₂ CF ₃ ), 1,1,1,5 5,6,6,6-octafluoro-2,4-hexanedionate (R ₁ : CF ₃ , R ₂ : CF ₂ CF ₃ ),

1-fluoro-2,4-heptane dionate (R ₁ : CH ₂ F, R ₂ : CH ₂ CH ₂ CH ₃ ), 1,1,1-trifluoro-2,4-heptane dionate (R ₁ : CF ₃ , R ₂ : CH ₂ CH ₂ CH ₃ ), 7-fluoro-2,4-heptanedionate (R ₁ : CH ₃ , R ₂ : CH ₂ CH ₂ CH ₂ F), 7,7,7- Trifluoro-2,4-heptane dionate (R ₁ : CH ₃ , R ₂ : CH ₂ CH ₂ CF ₃ ), 6,6,7,7,7-pentafluoro-2,4-heptane dionate (R ₁ : CH ₃ , R ₂ : CH ₂ CF ₂ CF ₃ ), 5, 5, 6, 6, 7, 7, 7-heptafluoro-2,4-heptane dionate (R ₁ : CH ₃ , R ₂ : _{CF 2 CF 2 CF 3),} 1,1,1,5,5,6,6,7,7,7- decafluoro 2,4 heptanedionate diisocyanate ( _{1: CF 3, R 2:} CF 2 CF 2 CF 3),

1-fluoro-3,5-heptane dionate (R ₁ : CH ₂ CH ₂ F, R ₂ : CH ₂ CH ₃ ), 1,1,1-trifluoro-3,5-heptane dionate (R ₁ : CH ₂ CF ₃ , R ₂ : CH ₂ CH ₃ ), 1,1,1,2,2-pentafluoro-3,5-heptanedionate (R ₁ : CF ₂ CF ₃ , R ₂ : CH ₂ CH ₃ ), 1,1,1,2,2,6,6,6-octafluoro-3,5-heptanedionate (R ₁ : CF ₂ CF ₃ , R ₂ : CH ₂ CF ₃ ), 1,1, Β-diketone type enolate such as 1,2,2,5,5,6,6,6-decafluoro-3,5-heptanedionate (R ₁ : CF ₂ CF ₃ , R ₂ : CH ₂ CF ₃ ) System anions;

Enolate anion of methyl acetoacetate, enolate anion of ethyl acetoacetate, enolate anion of trifluoromethyl acetoacetate, enolate anion of 2,2,2-trifluoroethyl acetoacetate, enolate anion of pentafluoroethyl acetoacetate, 2-methylacetate Enolate anion of methyl acetate, enolate anion of methyl 2-ethylacetoacetate, enolate anion of methyl trifluoroacetoacetate, enolate anion of ethyl trifluoroacetoacetate, enolate anion of trifluoromethyl trifluoroacetoacetate, trifluoroacetoacetate 2, Β-ketoester type enolates such as enolate anion of 2,2-trifluoroethyl and enolate anion of pentafluoroethyl trifluoroacetoacetate ON, enolate anion of dimethyl malonate, enolate anion of diethyl malonate, enolate anion of dimethyl 2-methylmalonate, enolate anion of diethyl 2-methylmalonate, enolate anion of dimethyl 2-ethylmalonate, 2-ethylmalon Β-diester type enolate system such as enolate anion of diethyl sulfonate, enolate anion of ditrifluoromethyl malonate, enolate anion of bis (2,2,2-trifluoroethyl) malonate, enolate anion of dipentafluoroethyl malonate Anions.

  Among the above, 2,4-pentanedionate (acetylacetonate), 2,4-hexanedionate, 2,4-heptanedionate, 3,5-heptanedionate from the viewpoint of electrochemical stability 1,3-cyclobutane dionate, 1,3-cyclopentane dionate, 1,3-cyclohexane dionate, 1,3-cycloheptane dionate, 1-fluoro-2,4-pentanedionate, 1,1 -Difluoro-2,4-pentanedionate, 1,1,1-trifluoro-2,4-pentanedionate (trifluoroacetylacetonate), 1,1,1,5-tetrafluoro-2,4- Pentandionate, 1,1,1,5,5-pentafluoro-2,4-pentanedionate, 1,1,1,5,5,5-hexafluoro-2,4-pe Tandionate (hexafluoroacetylacetonate), 6-fluoro-2,4-hexane dionate, 1-fluoro-2,4-hexane dionate, 1,1-difluoro-2,4-hexane dionate, 1,1 1,6-trifluoro-2,4-hexanedionate, 6-fluoro-2,4-hexanedionate, 6,6-difluoro-2,4-hexanedionate, 6,6,6-trifluoro-2 , 4-hexane dionate, 1,6,6,6-tetrafluoro-2,4-hexane dionate, 1,1,6,6,6-pentafluoro-2,4-hexane dionate, 1,1 , 1,6,6,6-Hexafluoro-2,4-hexane dionate, 5,5,6,6,6-pentafluoro-2,4-hexane dionate, 1,1,1,5,5 , 6, Preferably β- diketone enolate based anions such as 6-octafluoro-2,4-hexanedionato diisocyanate,

Further, from the viewpoint of lowering the melting point, 2,4-hexane dionate, 2,4-heptane dionate, 2,4-octane dionate, 3,5-octane dionate, 1-fluoro-2,4- Pentandionate, 1,1-difluoro-2,4-pentandionate, 1,1,1-trifluoro-2,4-pentanedionate, 1,1,1,5-tetrafluoro-2,4- Pentane dionate, 1,1,1,5,5-pentafluoro-2,4-pentane dionate, 1-fluoro-2,4-hexane dionate, 1,1-difluoro-2,4-hexane dionate 1,1,1-trifluoro-2,4-hexanedionate, 6-fluoro-2,4-hexanedionate, 6,6-difluoro-2,4-hexanedionate, 6,6,6- Trifluoro- , 4-hexane dionate, 1,6,6,6-tetrafluoro-2,4-hexane dionate, 1,1,6,6,6-pentafluoro-2,4-hexane dionate, 1,1 , 1,6,6,6-hexafluoro-2,4-hexane dionate, 5,5,6,6,6-pentafluoro-2,4-hexane dionate, 1,1,1,5,5 Β-diketone type enolate anion having an asymmetric structure such as, 6,6,6-octafluoro-2,4-hexanedionate,

Particularly, 1,1,1-trifluoro-2,4-pentanedionate (trifluoroacetylacetonate), 1,1,1-trifluoro-2,4-hexanedionate from the viewpoint of lowering the viscosity. , Fluorinated alkyl groups such as 6,6,6-trifluoro-2,4-hexanedionate, 1,1,1,5,5,6,6,6-octafluoro-2,4-hexanedionate A β-diketone enolate anion having an asymmetric structure is most preferable. These β-carbonyl enolate anions may be used in combination of two or more.

  Examples of the cation of the ionic liquid of the present invention include an organic cation, and a nitrogen-containing organic cation is more preferable from the viewpoint of a low melting point. Examples of the nitrogen-containing organic cation include an imidazolium cation, a pyrrolidinium cation, a piperidinium cation, and a quaternary ammonium cation. Among these, an imidazolium cation is preferable from the viewpoint of conductivity.

  As such an imidazolium-based cation, an N-substituted imidazolium cation (N-1 substituted type, N, N-2 substituted type) in which an alkyl group is bonded to a nitrogen atom of an imidazolium skeleton, for ease of synthesis, Further, an N, C substituted imidazolium cation (N, C-2 substituted type, N, N, C-3 substituted type, N, N, C, C--) in which an alkyl group is bonded to the carbon atom of the imidazolium skeleton. 4-substitution type, N, N, C, C, C-total substitution type) is preferred. Note that the alkyl group herein may include a halogen, ether oxygen, ether sulfur, and / or a cyano group. More preferably, from the viewpoint of viscosity reduction, imidazolium having 3 or less substitutions such as N-1 substitution type, N, N-2 substitution type, N, C-2 substitution type, N, N, C-3 substitution type, etc. More preferably, from the viewpoint of lowering the viscosity, imidazolium having 10 or less carbon atoms in each substituted alkyl group is preferred.

  Specifically, examples of the imidazolium cation used in the present invention include the following. In addition, halogenated alkyl groups such as partially fluorinated alkyl groups and fully fluorinated alkyl groups of the following examples are also exemplified.

Examples of N-1 substituted imidazolium-based cations include:
1-methylimidazolium, 1-ethylimidazolium, 1-propylimidazolium, 1-butylimidazolium, 1-pentylimidazolium, 1-hexylimidazolium, 1-heptylimidazolium, 1-octylimidazolium, 1- Alkyl substituted imidazoliums such as nonylimidazolium, 1-decylimidazolium;

1-methoxymethylimidazolium, 1- (2-methoxyethyl) imidazolium, 1- (3-methoxypropyl) imidazolium, 1- (4-methoxybutyl) imidazolium, 1- (5-methoxypentyl) imidazolium 1- (6-methoxyhexyl) imidazolium, 1- (7-methoxyheptyl) imidazolium, 1- (8-methoxyoctyl) imidazolium, 1-ethoxymethylimidazolium, 1- (2-ethoxyethyl) imidazole 1- (3-ethoxypropyl) imidazolium, 1- (4-ethoxybutyl) imidazolium, 1- (5-ethoxypentyl) imidazolium, 1- (6-ethoxyhexyl) imidazolium, 1-propoxymethyl Imidazolium, 1- (2-propoxyethyl) imidazolium Substituted with alkyl groups containing ether oxygen such as 1- (3-propoxypropyl) imidazolium, 1- (4-propoxybutyl) imidazolium, 1- (5-propoxypentyl) imidazolium, 1-ethoxyethoxyethylimidazolium Made imidazolium;

1-methylthiomethylimidazolium, 1- (2-methylthioethyl) imidazolium, 1- (3-methylthiopropyl) imidazolium, 1- (4-methylthiobutyl) imidazolium, 1-ethylthiomethylimidazolium, 1- Imidazolium substituted with an alkyl group containing ether sulfur such as (2-ethylthioethyl) imidazolium, 1- (3-ethylthiopropyl) imidazolium, 1- (3-ethylthiobutyl) imidazolium;

1-cyanomethylimidazolium, 1- (2-cyanoethyl) imidazolium, 1- (3-cyanopropyl) imidazolium, 1- (4-cyanobutyl) imidazolium, 1-dicyanomethylimidazolium, 1- (2, And imidazolium substituted with an alkyl group containing a cyano group such as 3-dicyanoethyl) imidazolium and 1- (2,3-dicyanopropyl) imidazolium. These N-1 substituted imidazoliums all have asymmetric structures.

  Examples of N, N-2 substituted imidazolium-based cations include 1,3-dimethylimidazolium, 1,3-diethylimidazolium, 1,3-dipropylimidazolium, 1,3-dibutylimidazolium, 1,3-dipentyl imidazolium, 1,3-dihexyl imidazolium, 1,3-bis (methoxymethyl) imidazolium, 1,3-bis (2-methoxyethyl) imidazolium, 1,3-bis (ethoxy) Methyl) imidazolium, 1,3-bis (2-ethoxyethyl) imidazolium, 1,3-bis (methylthiomethyl) imidazolium, 1,3-bis (2-methylthioethyl) imidazolium, 1,3-bis (Ethylthiomethyl) imidazolium, 1,3-bis (2-ethylthioethyl) imidazolium, 1,3-bis ( Aminomethyl) imidazolium, 1,3-bis (2-cyanoethyl) imidazolium, 1,3-bis (3-cyanopropyl) imidazolium, 1,3-bis (4-cyanobutyl) imidazolium, etc. N, N-2 substituted imidazolium;

1-methyl-3-ethylimidazolium, 1-methyl-3-propylimidazolium, 1-methyl-3-butylimidazolium, 1-methyl-3-propylimidazolium, 1-methyl-3-butylimidazolium, 1-methyl-3-pentylimidazolium, 1-methyl-3-hexylimidazolium, 1-methyl-3-heptylimidazolium, 1-methyl-3-octylimidazolium, 1-methyl-3-nonylimidazolium, 1-methyl-3-decylimidazolium, 1-ethyl-3-propylimidazolium, 1-ethyl-3-butylimidazolium, 1-ethyl-3-pentylimidazolium, 1-ethyl-3-hexylimidazolium, 1-ethyl-3-heptyluimidazolium, 1-ethyl-3-octylloumidazolium , 1-propyl-3-butyl imidazolium, 1-propyl-3-pentyl imidazolium, 1-propyl-3-hexyl imidazolium, 1-butyl-3-pentyl imidazolium,

1-butyl-3-hexylimidazolium, 1-methyl-3-methoxymethylimidazolium, 1-methyl-3- (2-methoxyethyl) imidazolium, 1-methyl-3- (3-methoxypropyl) imidazolium 1-methyl-3- (4-methoxybutyl) imidazolium, 1-methyl-3-ethoxymethylimidazolium, 1-methyl-3- (2-ethoxyethyl) imidazolium, 1-methyl-3- (3 -Ethoxypropyl) imidazolium, 1-methyl-3- (4-ethoxybutyl) imidazolium, 1-ethyl-3-methoxymethylimidazolium, 1-ethyl-3- (2-methoxyethyl) imidazolium, 1- Ethyl-3- (3-methoxypropyl) imidazolium, 1-ethyl-3-ethoxymethylimidazolium, 1- Til-3- (2-ethoxyethyl) imidazolium, 1-ethyl-3- (3-ethoxypropyl) imidazolium, 1-ethyl-3- (4-ethoxybutyl) imidazolium, 1-ethyl-3-propoxy Methyl imidazolium,

1-ethyl-3- (2-propoxyethyl) imidazolium, 1-ethyl-3- (3-propoxypropyl) imidazolium, 1-propyl-3-methoxymethylimidazolium, 1-propyl-3- (2- Methoxyethyl) imidazolium, 1-propyl-3- (3-methoxypropyl) imidazolium, 1-propyl-3-ethoxymethylimidazolium, 1-propyl-3- (2-ethoxyethyl) imidazolium, 1-propyl -3- (3-ethoxypropyl) imidazolium, 1-propyl-3- (4-ethoxybutyl) imidazolium, 1-propyl-3-propoxymethylimidazolium, 1-propyl-3- (2-propoxyethyl) Imidazolium, 1-propyl-3- (3-propoxypropyl) imidazolium, 1- Chill -3-methoxy-methylimidazolium, 1-butyl-3- (2-methoxyethyl) imidazolium,

1-butyl-3- (3-methoxypropyl) imidazolium, 1-butyl-3-ethoxymethylimidazolium, 1-butyl-3- (2-ethoxyethyl) imidazolium, 1-butyl-3- (3- Ethoxypropyl) imidazolium, 1-butyl-3-propoxymethylimidazolium, 1-butyl-3- (2-propoxyethyl) imidazolium, 1-butyl-3- (3-propoxypropyl) imidazolium, 1-pentyl -3-methoxymethylimidazolium, 1-pentyl-3- (2-methoxyethyl) imidazolium, 1-pentyl-3- (3-methoxypropyl) imidazolium, 1-pentyl-3-ethoxymethylimidazolium, 1 -Pentyl-3- (2-ethoxyethyl) imidazolium, 1-hexyl-3-methoxy Chill imidazolium, 1-hexyl-3- (2-methoxyethyl) imidazolium, 1-hexyl-3-ethoxy-methylimidazolium,

1-hexyl-3- (2-ethoxyethyl) imidazolium, 1-methyl-3-methylthiomethylimidazolium, 1-methyl-3- (2-methylthioethyl) imidazolium, 1-methyl-3- (3- Methylthiopropyl) imidazolium, 1-methyl-3- (4-methylthiobutyl) imidazolium, 1-methyl-3-ethylthiomethylimidazolium, 1-methyl-3- (2-ethylthioethyl) imidazolium, 1 -Methyl-3- (3-ethylthiopropyl) imidazolium, 1-methyl-3- (4-ethylthiobutyl) imidazolium, 1-ethyl-3- (methylthiomethyl) imidazolium, 1-ethyl-3- (2-methylthioethyl) imidazolium, 1-ethyl-3- (3-methylthiopropyl) imidazolium, 1-ethyl -3-ethylthiomethylimidazolium, 1-ethyl-3- (2-ethylthioethyl) imidazolium, 1-ethyl-3- (3-ethylthiopropyl) imidazolium, 1-ethyl-3- (4- Ethylthiobutyl) imidazolium, 1-ethyl-3-propylthiomethylimidazolium, 1-ethyl-3- (2-propylthioethyl) imidazolium, 1-ethyl-3- (3-propylthiopropyl) imidazolium 1-propyl-3-methylthiomethylimidazolium, 1-propyl-3- (2-methylthioethyl) imidazolium, 1-propyl-3- (3-methylthiopropyl) imidazolium, 1-propyl-3-ethylthio Methyl imidazolium, 1-propyl-3- (2-ethylthioethyl) imidazolium,

1-propyl-3- (3-ethylthiopropyl) imidazolium, 1-propyl-3- (4-ethylthiobutyl) imidazolium, 1-propyl-3-propylthiomethylimidazolium, 1-propyl-3- (2-propylthioethyl) imidazolium, 1-propyl-3- (3-propylthiopropyl) imidazolium, 1-butyl-3-methylthiomethylimidazolium, 1-butyl-3- (2-methylthioethyl) imidazo 1-butyl-3- (3-methylthiopropyl) imidazolium, 1-butyl-3-ethylthiomethylimidazolium, 1-butyl-3- (2-ethylthioethyl) imidazolium, 1-butyl-3 -(3-ethylthiopropyl) imidazolium, 1-butyl-3-propylthiomethylimidazolium, -Butyl-3- (2-propylthioethyl) imidazolium, 1-butyl-3- (3-propylthiopropyl) imidazolium, 1-pentyl-3-methylthiomethylimidazolium, 1-pentyl-3- (2 -Methylthioethyl) imidazolium, 1-pentyl-3- (3-methylthiopropyl) imidazolium, 1-pentyl-3-ethylthiomethylimidazolium, 1-pentyl-3- (2-ethylthioethyl) imidazolium, 1-hexyl-3-methylthiomethylimidazolium, 1-hexyl-3- (2-methylthioethyl) imidazolium, 1-hexyl-3-ethylthiomethylimidazolium, 1-hexyl-3- (2-ethylthioethyl) ) Imidazolium, 1-methyl-3-cyanomethylimidazolium,

1-methyl-3- (2-cyanoethyl) imidazolium, 1-methyl-3- (3-cyanopropyl) imidazolium, 1-methyl-3- (4-cyanobutyl) imidazolium, 1-methyl-3- ( 5-cyanopentyl) imidazolium, 1-methyl-3- (6-cyanohexyl) imidazolium, 1-ethyl-3-cyanomethylimidazolium, 1-ethyl-3- (2-cyanoethyl) imidazolium, 1- Ethyl-3- (3-cyanopropyl) imidazolium, 1-ethyl-3- (4-cyanobutyl) imidazolium, 1-ethyl-3- (5-cyanopentyl) imidazolium, 1-ethyl-3- (6 -Cyanohexyl) imidazolium, 1-propyl-3-cyanomethylimidazolium, 1-propyl-3- (2-cyanoethyl) imidazole 1-propyl-3- (3-cyanopropyl) imidazolium, 1-propyl-3- (4-cyanobutyl) imidazolium, 1-butyl-3-cyanomethylimidazolium, 1-butyl-3- (2 -Cyanoethyl) imidazolium, 1-butyl-3- (3-cyanopropyl) imidazolium, 1-butyl-3- (4-cyanobutyl) imidazolium, 1-methyl-3-dicyanomethylimidazolium, 1-methyl- 3- (2,3-dicyanoethyl) imidazolium, 1-methyl-3- (2,3-dicyanopropyl) imidazolium, 1-ethyl-3-dicyanomethylimidazolium, 1-ethyl-3- (2, 3-dicyanoethyl) imidazolium, 1-ethyl-3- (2,3-dicyanopropyl) imidazolium, 1-propyl-3 Dicyano-methylimidazolium, 1-propyl-3- (2,3-dicyano-ethyl) imidazolium,

1-propyl-3- (2,3-dicyanopropyl) imidazolium, 1-methoxymethyl-3- (2-methoxyethyl) imidazolium, 1-methoxymethyl-3- (2-methoxypropyl) imidazolium, 1 -(2-methoxyethyl) -3-ethoxymethylimidazolium, 1- (2-methoxyethyl) -3- (3-methoxypropyl) imidazolium, 1- (2-methoxyethyl) -3- (2-ethoxy Ethyl) imidazolium, 1-ethoxymethyl-3- (2-ethoxyethyl) imidazolium, 1-ethoxymethyl-3- (2-ethoxypropyl) imidazolium, 1- (2-ethoxyethyl) -3- (3 -Ethoxypropyl) imidazolium, 1- (2-ethoxyethyl) -3- (3-propoxypropyl) imidazolium, 1 Methoxymethyl-3- (2-methylthiomethyl) imidazolium, 1-methoxymethyl-3- (2-methylthioethyl) imidazolium, 1-methoxymethyl-3- (2-ethylthioethyl) imidazolium, 1- ( 2-methoxyethyl) -3-methylthiomethylimidazolium, 1- (2-methoxyethyl) -3- (2-methylthioethyl) imidazolium, 1- (2-methoxyethyl) -3-ethylthiomethylimidazolium, 1- (2-methoxyethyl) -3- (2-ethylthioethyl) imidazolium, 1-ethoxymethyl-3-methylthiomethylimidazolium, 1-ethoxymethyl-3- (2-methylthioethyl) imidazolium,

1-ethoxymethyl-3-ethylthiomethylimidazolium, 1-ethoxymethyl-3- (2-ethylthioethyl) imidazolium, 1- (2-ethoxyethyl) -3-methylthiomethylimidazolium, 1- (2 -Ethoxyethyl) -3- (2-methylthioethyl) imidazolium, 1- (2-ethoxyethyl) -3- (2-ethylthioethyl) imidazolium, 1-methoxymethyl-3-cyanomethylimidazolium, 1 -Methoxymethyl-3- (2-cyanoethyl) imidazolium, 1-methoxymethyl-3- (3-cyanopropyl) imidazolium, 1-methoxymethyl-3- (4-cyanobutyl) imidazolium, 1-methoxymethyl- 3- (5-Cyanopentyl) imidazolium, 1-methoxymethyl-3- (6-cyanohexyl ) Imidazolium, 1- (2-methoxyethyl) -3-cyanomethylimidazolium, 1- (2-methoxyethyl) -3- (2-cyanoethyl) imidazolium, 1- (2-methoxyethyl) -3- (3-cyanopropyl) imidazolium, 1- (2-methoxyethyl) -3- (4-cyanobutyl) imidazolium, 1- (2-methoxyethyl) -3- (5-cyanopentyl) imidazolium, 1- (2-methoxyethyl) -3- (6-cyanohexyl) imidazolium, 1- (3-methoxypropyl) -3-cyanomethylimidazolium, 1- (3-methoxypropyl) -3- (2-cyanoethyl) Imidazolium, 1- (3-methoxypropyl) -3- (3-cyanopropyl) imidazolium, 1- (3-methoxypropyl) -3- ( -Cyanobutyl) imidazolium, 1- (4-methoxybutyl) -3-cyanomethylimidazolium, 1- (4-methoxybutyl) -3- (2-cyanoethyl) imidazolium, 1- (4-methoxybutyl)- 3- (3-cyanopropyl) imidazolium,

1- (4-methoxybutyl) -3- (4-cyanobutyl) imidazolium, 1-ethoxymethyl-3-cyanomethylimidazolium, 1-ethoxymethyl-3- (2-cyanoethyl) imidazolium, 1-ethoxymethyl -3- (3-cyanopropyl) imidazolium, 1-ethoxymethyl-3- (4-cyanobutyl) imidazolium, 1-ethoxymethyl-3- (5-cyanopentyl) imidazolium, 1-ethoxymethyl-3- (6-cyanohexyl) imidazolium, 1- (2-ethoxyethyl) -3-cyanomethylimidazolium, 1- (2-ethoxyethyl) -3- (2-cyanoethyl) imidazolium, 1- (2-ethoxy Ethyl) -3- (3-cyanopropyl) imidazolium, 1- (2-ethoxyethyl) -3- (4-sia) Butyl) imidazolium, 1- (2-ethoxyethyl) -3- (5-cyanopentyl) imidazolium, 1- (2-ethoxyethyl) -3- (6-cyanohexyl) imidazolium, 1- (3- Ethoxypropyl) -3-cyanomethylimidazolium, 1- (3-ethoxypropyl) -3- (2-cyanoethyl) imidazolium, 1- (3-ethoxypropyl) -3- (3-cyanopropyl) imidazolium, 1- (3-ethoxypropyl) -3- (4-cyanobutyl) imidazolium,

1- (4-ethoxybutyl) -3-cyanomethylimidazolium, 1- (4-ethoxybutyl) -3- (2-cyanoethyl) imidazolium, 1- (4-ethoxybutyl) -3- (3-cyano Propyl) imidazolium, 1- (4-ethoxybutyl) -3- (4-cyanobutyl) imidazolium, 1-propoxymethyl-3-cyanomethylimidazolium, 1-propoxymethyl-3- (2-cyanoethyl) imidazolium 1-propoxymethyl-3- (3-cyanopropyl) imidazolium, 1-propoxymethyl-3- (4-cyanobutyl) imidazolium, 1-propoxymethyl-3- (5-cyanopentyl) imidazolium, 1- Propoxymethyl-3- (6-cyanohexyl) imidazolium, 1- (2-propoxyethyl)- -Cyanomethylimidazolium, 1- (2-propoxyethyl) -3- (2-cyanoethyl) imidazolium, 1- (2-propoxyethyl) -3- (3-cyanopropyl) imidazolium, 1- (2- Propoxyethyl) -3- (4-cyanobutyl) imidazolium, 1- (2-propoxyethyl) -3- (5-cyanopentyl) imidazolium, 1- (2-propoxyethyl) -3- (6-cyanohexyl) ) Imidazolium, 1- (3-propoxypropyl) -3-cyanomethylimidazolium, 1- (3-propoxypropyl) -3- (2-cyanoethyl) imidazolium, 1- (3-propoxypropyl) -3- (3-Cyanopropyl) imidazolium, 1- (3-propoxypropyl) -3- (4-cyanobutyl) imidazolium ,

1-merthiomethyl-3- (2-methylthioethyl) imidazolium, 1-methylthiomethyl-3- (2-ethylthioethyl) imidazolium, 1- (2-methylthioethyl) -3- (2-ethylthioethyl) Imidazolium, 1- (2-ethylthiomethyl) -3- (2-ethylthioethyl) imidazolium, 1- (2-ethylthioethyl) -3- (3-methylthiopropyl) imidazolium, 1- (2 -Ethylthioethyl) -3- (2-propylthioethyl) imidazolium, 1-methylthiomethyl-3-cyanomethylimidazolium, 1-methylthiomethyl-3- (2-cyanoethyl) imidazolium, 1-methylthiomethyl- 3- (3-Cyanopropyl) imidazolium, 1-methylthiomethyl-3- (4-cyanobutyl) imidazoli 1-methylthiomethyl-3- (5-cyanopentyl) imidazolium, 1-methylthiomethyl-3- (6-cyanohexyl) imidazolium, 1- (2-methylthioethyl) -3-cyanomethylimidazolium, 1- (2-methylthioethyl) -3- (2-cyanoethyl) imidazolium,

1- (2-Merylthioethyl) -3- (3-cyanopropyl) imidazolium, 1- (2-methylthioethyl) -3- (4-cyanobutyl) imidazolium, 1- (2-methylthioethyl) -3 -(5-cyanopentyl) imidazolium, 1- (2-methylthioethyl) -3- (6-cyanohexyl) imidazolium, 1- (3-methylthiopropyl) -3-cyanomethylimidazolium, 1- (3 -Methylthiopropyl) -3- (2-cyanoethyl) imidazolium, 1- (3-methylthiopropyl) -3- (3-cyanopropyl) imidazolium, 1- (3-methylthiopropyl) -3- (4-cyanobutyl) ) Imidazolium, 1- (4-methylthiobutyl) -3-cyanomethylimidazolium, 1- (4-methylthiobutyl) -3- ( -Cyanoethyl) imidazolium, 1- (4-methylthiobutyl) -3- (3-cyanopropyl) imidazolium, 1- (4-methylthiobutyl) -3- (4-cyanobutyl) imidazolium, 1-ethylthiomethyl -3-Cyanomethylimidazolium, 1-ethylthiomethyl-3- (2-cyanoethyl) imidazolium, 1-ethylthiomethyl-3- (3-cyanopropyl) imidazolium, 1-ethylthiomethyl-3- ( 4-cyanobutyl) imidazolium, 1-ethylthiomethyl-3- (5-cyanopentyl) imidazolium, 1-ethylthiomethyl-3- (6-cyanohexyl) imidazolium, 1- (2-ethylthioethyl) -3-Cyanomethylimidazolium, 1- (2-ethylthioethyl) -3- (2-cyanoethyl) imi Zoriumu, 1- (2-ethyl thioethyl) -3- (3-cyanopropyl) imidazolium, 1- (2-ethyl thioethyl) -3- (4-cyanobutyl) imidazolium,

1- (2-ethylthioethyl) -3- (5-cyanopentyl) imidazolium, 1- (2-ethylthioethyl) -3- (6-cyanohexyl) imidazolium, 1- (3-ethylthiopropyl) ) -3-Cyanomethylimidazolium, 1- (3-ethylthiopropyl) -3- (2-cyanoethyl) imidazolium, 1- (3-ethylthiopropyl) -3- (3-cyanopropyl) imidazolium 1- (3-ethylthiopropyl) -3- (4-cyanobutyl) imidazolium, 1- (4-ethylthiobutyl) -3-cyanomethylimidazolium, 1- (4-ethylthiobutyl) -3- (2-cyanoethyl) imidazolium, 1- (4-ethylthiobutyl) -3- (3-cyanopropyl) imidazolium, 1- (4-ethylthiobutyl) -3- 4-cyanobutyl) imidazolium, 1-cyanomethyl-3- (2-cyanoethyl) imidazolium, 1-cyanomethyl-3- (3-cyanopropyl) imidazolium, 1-cyanomethyl-3- (4-cyanobutyl) imidazolium, 1-cyanomethyl-3- (5-cyanopentyl) imidazolium, 1-cyanomethyl-3- (6-cyanohexyl) imidazolium, 1- (2-cyanoethyl) -3- (3-cyanopropyl) imidazolium, 1 -(2-cyanoethyl) -3- (4-cyanobutyl) imidazolium, 1- (2-cyanoethyl) -3- (5-cyanopentyl) imidazolium, 1- (2-cyanoethyl) -3- (6-cyano (Hexyl) imidazolium, 1- (3-cyanopropyl) -3- (4-cyanobutyl) imidazolium N having an asymmetric structure such as, include imidazolium N-2 substituted.

  Examples of the N, C-2 substituted imidazolium cation include 1,2-dimethylimidazolium, 1-methyl-2-ethylimidazolium, 1-methyl-2-propylimidazolium, and 1-methyl-2. -Butylimidazolium, 1-methyl-2-propylimidazolium, 1-methyl-2-butylimidazolium, 1-methyl-2-pentylimidazolium, 1-methyl-2-hexylimidazolium, 1-methyl-2 -Heptylimidazolium, 1-methyl-2-octylimidazolium, 1-methyl-2-nonylimidazolium, 1-methyl-2-decylimidazolium, 1-ethyl-2-methylimidazolium, 1,2-diethyl Imidazolium, 1-ethyl-2-propylimidazolium, 1-ethyl-2-butylimidazolium 1-ethyl-2-pentylimidazolium, 1-ethyl-2-hexylimidazolium, 1-ethyl-2-heptyluimidazolium, 1-ethyl-2-octylruylimidazolium, 1-propyl-2-methylimidazolium 1-propyl-2-ethylimidazolium, 1,2-dipropylimidazolium, 1-propyl-2-butylimidazolium, 1-propyl-2-pentylimidazolium, 1-propyl-2-hexylimidazolium 1-butyl-2-methylimidazolium, 1-butyl-2-ethylimidazolium,

1-butyl-2-propylimidazolium, 1,2-dibutylimidazolium, 1-butyl-2-pentylimidazolium, 1-butyl-2-hexylimidazolium, 1-pentyl-2-methylimidazolium, 1-butyl-2-propylimidazolium Pentyl-2-ethylimidazolium, 1-pentyl-2-propylimidazolium, 1-pentyl-2-butylimidazolium, 1,2-dipentyl imidazolium, 1-hexyl-2-methylimidazolium, 1-hexyl 2-ethylimidazolium, 1-hexyl-2-propylimidazolium, 1-hexyl-2-butylimidazolium, 1-hexyl-2-pentylimidazolium, 1-heptyl-2-methylimidazolium, 1-heptyl 2-Ethylimidazolium, 1-octyl-2-methylimidazole Um, 1-octyl-2-ethyl imidazolium, 1-nonyl-2-methylimidazolium, 1-decyl-2-methylimidazolium, 1,2-dihexyl imidazolium,

1-methyl-2-methoxymethylimidazolium, 1-methyl-2- (2-methoxyethyl) imidazolium, 1-methyl-2- (3-methoxypropyl) imidazolium, 1-methyl-2- (4- Methoxybutyl) imidazolium, 1-methyl-2-ethoxymethylimidazolium, 1-methyl-2- (2-ethoxyethyl) imidazolium, 1-methyl-2- (3-ethoxypropyl) imidazolium, 1-methyl 2- (4-Ethoxybutyl) imidazolium, 1-ethyl-2-methoxymethylimidazolium, 1-ethyl-2- (2-methoxyethyl) imidazolium, 1-ethyl-2- (3-methoxypropyl) Imidazolium, 1-ethyl-2-ethoxymethylimidazolium, 1-ethyl-2- (2-ethoxyethyl) imidazole 1-ethyl-2- (3-ethoxypropyl) imidazolium, 1-ethyl-2- (4-ethoxybutyl) imidazolium, 1-ethyl-2-propoxymethylimidazolium, 1-ethyl-2- ( 2-propoxyethyl) imidazolium, 1-ethyl-2- (3-propoxypropyl) imidazolium, 1-propyl-2-methoxymethylimidazolium, 1-propyl-2- (2-methoxyethyl) imidazolium, 1 -Propyl-2- (3-methoxypropyl) imidazolium, 1-propyl-2-ethoxymethylimidazolium, 1-propyl-2- (2-ethoxyethyl) imidazolium, 1-propyl-2- (3-ethoxy Propyl) imidazolium, 1-propyl-2- (4-ethoxybutyl) imidazolium, Propyl-2-propoxymethyl imidazolium, 1-propyl-2- (2-propoxy-ethyl) imidazolium, 1-propyl-2- (3-propoxy-propyl) imidazolium,

1-butyl-2-methoxymethylimidazolium, 1-butyl-2- (2-methoxyethyl) imidazolium, 1-butyl-2- (3-methoxypropyl) imidazolium, 1-butyl-2-ethoxymethylimidazolium 1-butyl-2- (2-ethoxyethyl) imidazolium, 1-butyl-2- (3-ethoxypropyl) imidazolium, 1-butyl-2-propoxymethylimidazolium, 1-butyl-2- ( 2-propoxyethyl) imidazolium, 1-butyl-2- (3-propoxypropyl) imidazolium, 1-pentyl-2-methoxymethylimidazolium, 1-pentyl-2- (2-methoxyethyl) imidazolium, 1 -Pentyl-2- (3-methoxypropyl) imidazolium, 1-pentyl-2-ethoxymethyl Imidazolium, 1-pentyl-2- (2-ethoxyethyl) imidazolium, 1-hexyl-2-methoxy-methylimidazolium, 1-hexyl-2- (2-methoxyethyl) imidazolium,

1-hexyl-2-ethoxymethylimidazolium, 1-hexyl-2- (2-ethoxyethyl) imidazolium, 1-methyl-2-methylthiomethylimidazolium, 1-methyl-2- (2-methylthioethyl) imidazole 1-methyl-2- (3-methylthiopropyl) imidazolium, 1-methyl-2- (4-methylthiobutyl) imidazolium, 1-methyl-2-ethylthiomethylimidazolium, 1-methyl-2- (2-ethylthioethyl) imidazolium, 1-methyl-2- (3-ethylthiopropyl) imidazolium, 1-methyl-2- (4-ethylthiobutyl) imidazolium, 1-ethyl-2-methylthiomethyl Imidazolium, 1-ethyl-2- (2-methylthioethyl) imidazolium,

1-ethyl-2- (3-methylthiopropyl) imidazolium, 1-ethyl-2-ethylthiomethylimidazolium, 1-ethyl-2- (2-ethylthioethyl) imidazolium, 1-ethyl-2- ( 3-ethylthiopropyl) imidazolium, 1-ethyl-2- (4-ethylthiobutyl) imidazolium, 1-ethyl-2-propylthiomethylimidazolium, 1-ethyl-2- (2-propylthioethyl) Imidazolium, 1-ethyl-2- (3-propylthiopropyl) imidazolium, 1-propyl-2-methylthiomethylimidazolium, 1-propyl-2- (2-methylthioethyl) imidazolium, 1-propyl-2 -(3-methylthiopropyl) imidazolium, 1-propyl-2-ethylthiomethylimidazolium, 1- Lopyl-2- (2-ethylthioethyl) imidazolium, 1-propyl-2- (3-ethylthiopropyl) imidazolium, 1-propyl-2- (4-ethylthiobutyl) imidazolium, 1-propyl- 2-propylthiomethylimidazolium, 1-propyl-2- (2-propylthioethyl) imidazolium, 1-propyl-2-(-propylthiopropyl) imidazolium, 1-butyl-2-methylthiomethylimidazolium, 1-butyl-2- (2-methylthioethyl) imidazolium, 1-butyl-2- (3-methylthiopropyl) imidazolium, 1-butyl-2-ethylthiomethylimidazolium, 1-butyl-2- (2 -Ethylthioethyl) imidazolium, 1-butyl-2- (3-ethylthiopropyl) imidazolium

1-butyl-2-propylthiomethylimidazolium, 1-butyl-2- (2-propylthioethyl) imidazolium, 1-butyl-2- (3-propylthiopropyl) imidazolium, 1-pentyl-2- Methylthiomethylimidazolium, 1-pentyl-2- (2-methylthioethyl) imidazolium, 1-pentyl-2- (3-methylthiopropyl) imidazolium, 1-pentyl-2-ethylthiomethylimidazolium, 1-pentyl 2- (2-ethylthioethyl) imidazolium, 1-hexyl-2-methylthiomethylimidazolium, 1-hexyl-2- (2-methylthioethyl) imidazolium, 1-hexyl-2-ethylthiomethylimidazole 1-hexyl-2- (2-ethylthioethyl) imidazolium, 1-hexyl Chill-2-cyano-methylimidazolium, 1-methyl-2-dicyano-methylimidazolium, 1-methyl-2- (2-cyanoethyl) imidazolium,

1-methyl-2- (2,3-dicyanoethyl) imidazolium, 1-methyl-2- (3-cyanopropyl) imidazolium, 1-methyl-2- (2,3-dicyanopropyl) imidazolium, 1 -Methyl-2- (4-cyanobutyl) imidazolium, 1-methyl-2- (5-cyanopentyl) imidazolium, 1-methyl-2- (6-cyanohexyl) imidazolium, 1-ethyl-2-cyano Methylimidazolium, 1-ethyl-2-dicyanomethylimidazolium, 1-ethyl-2- (2-cyanoethyl) imidazolium, 1-ethyl-2- (2,3-dicyanoethyl) imidazolium, 1-ethyl- 2- (3-cyanopropyl) imidazolium, 1-ethyl-2- (2,3-dicyanopropyl) imidazolium, 1-ethyl-2- (4 Cyanobutyl) imidazolium, 1-ethyl-2- (5-cyanopentyl) imidazolium, 1-ethyl-2- (6-cyanohexyl) imidazolium, 1-propyl-2-cyanomethylimidazolium, 1-propyl- 2-dicyanomethylimidazolium, 1-propyl-2- (2-cyanoethyl) imidazolium, 1-propyl-2- (2,3-dicyanoethyl) imidazolium, 1-propyl-2- (3-cyanopropyl) Imidazolium, 1-propyl-2- (2,3-dicyanopropyl) imidazolium, 1-propyl-2- (4-cyanobutyl) imidazolium, 1-butyl-2-cyanomethylimidazolium, 1-butyl-2 -(2-Cyanoethyl) imidazolium, 1-butyl-2- (3-cyanopropyl) imidazolium 1-butyl-2- (4-cyanobutyl) imidazolium, 1-methoxy-2-methyl imidazolium, 1- (2-methoxyethyl) -2-methylimidazolium,

1- (3-methoxypropyl) -2-methylimidazolium, 1- (4-methoxybutyl) -2-methylimidazolium, 1-ethoxymethyl-2-methylimidazolium, 1- (2-ethoxyethyl)- 2-methylimidazolium, 1- (3-ethoxypropyl) -2-methylimidazolium, 1- (4-ethoxybutyl) -2-methylimidazolium, 1-methoxymethyl-2-ethylimidazolium, 1- ( 2-methoxyethyl) -2-ethylimidazolium, 1- (3-methoxypropyl) -2-ethylimidazolium, 1-ethoxymethyl-2-ethylimidazolium, 1- (2-ethoxyethyl) -2-ethyl Imidazolium, 1- (3-ethoxypropyl) -2-ethylimidazolium, 1- (4-ethoxybutyl) -2-e Louis imidazolium, 1-propoxymethyl-2-ethylimidazolium, 1- (2-propoxyethyl) -2-ethylimidazolium, 1- (3-propoxypropyl) -2-ethylimidazolium, 1-methoxymethyl- 2-propylimidazolium, 1- (2-methoxyethyl) -2-propylimidazolium, 1- (3-methoxypropyl) -2-propylimidazolium, 1-ethoxymethyl-2-propylimidazolium, 1- ( 2-Ethoxyethyl) -2-propylimidazolium, 1- (3-ethoxypropyl) -2-propylimidazolium, 1- (4-ethoxybutyl) -2-propylimidazolium, 1-propoxymethyl-2-propyl Imidazolium, 1- (2-propoxyethyl) -2-propylimidazolium 1- (3-propoxy-propyl) -2-propyl imidazolium, 1-methoxy-2-butyl imidazolium, 1- (2-methoxyethyl) -2-butyl-imidazolium,

1- (3-methoxypropyl) -2-butylimidazolium, 1-ethoxymethyl-2-butylimidazolium, 1- (2-ethoxyethyl) -2-butylimidazolium, 1- (3-ethoxypropyl)- 2-butylimidazolium, 1-propoxymethyl-2-butylimidazolium, 1- (2-propoxyethyl) -2-butylimidazolium, 1- (3-propoxypropyl) -2-butylimidazolium, 1-methoxy Methyl-2-pentylimidazolium, 1- (2-methoxyethyl) -2-pentylimidazolium, 1- (3-methoxypropyl) -2-pentylimidazolium, 1-ethoxymethyl-2-pentylimidazolium, 1 -(2-Ethoxyethyl) -2-pentylimidazolium, 1-methoxymethyl-2-he Silimimidazolium, 1- (2-methoxyethyl) -2-hexylimidazolium, 1-ethoxymethyl-2-hexylimidazolium, 1- (2-ethoxyethyl) -2-hexylimidazolium, 1,2-bis (Methoxymethyl) imidazolium, 1-methoxymethyl-2- (2-methoxyethyl) imidazolium, 1-methoxymethyl-2-ethoxymethylimidazolium, 1-methoxymethyl-2- (2-ethoxyethyl) imidazolium 1- (2-methoxyethyl) -2-methoxymethylimidazolium, 1- (2-methoxyethyl) -2-ethoxymethylimidazolium, 1,2-bis (2-methoxyethyl) imidazolium, 1- ( 2-methoxyethyl) -2- (2-ethoxyethyl) imidazolium, 1-ethoxymethyl 2-methoxymethylimidazolium, 1-ethoxymethyl-2- (2-methoxyethyl) imidazolium, 1,2-bis (ethoxymethyl) imidazolium, 1-ethoxymethyl-2- (2-ethoxyethyl) imidazole 1- (2-ethoxyethyl) -2-methoxymethylimidazolium, 1- (2-ethoxyethyl) -2- (2-methoxyethyl) imidazolium, 1- (2-ethoxyethyl) -2-ethoxy Methyl imidazolium,

1,2-bis (2-ethoxyethyl) imidazolium, 1- (2-ethoxyethyl) -2- (3-ethoxypropyl) imidazolium, 1- (2-ethoxyethyl) -2- (3-propoxypropyl) ) Imidazolium, 1- (3-ethoxypropyl) -2-methoxymethylimidazolium, 1- (3-ethoxypropyl) -2- (2-methoxyethyl) imidazolium, 1- (3-ethoxypropyl) -2 -(2-ethoxymethyl) imidazolium, 1- (3-ethoxypropyl) -2- (2-ethoxyethyl) imidazolium, 1-methoxymethyl-2- (2-methylthioethyl) imidazolium, 1- (2 -Methoxyethyl) -2-ethylthiomethylimidazolium, 1- (2-methoxyethyl) -2- (2-ethylthioethyl) imidazole 1-ethoxymethyl-2- (2-ethylthioethyl) imidazolium, 1- (2-ethoxyethyl) -2- (3-ethylthiopropyl) imidazolium, 1- (2-ethoxyethyl) -2 -(3-propylthiopropyl) imidazolium, 1-methoxymethyl-2-cyanomethylimidazolium, 1-methoxymethyl-2- (2-cyanoethyl) imidazolium, 1-methoxymethyl-2- (3-cyanopropyl) ) Imidazolium, 1-methoxymethyl-2- (4-cyanobutyl) imidazolium, 1-methoxymethyl-2- (5-cyanopentyl) imidazolium, 1-methoxymethyl-2- (6-cyanohexyl) imidazolium ,

1- (2-methoxyethyl) -2-cyanomethylimidazolium, 1- (2-methoxyethyl) -2- (2-cyanoethyl) imidazolium, 1- (2-methoxyethyl) -2- (3-cyano Propyl) imidazolium, 1- (2-methoxyethyl) -2- (4-cyanobutyl) imidazolium, 1- (2-methoxyethyl) -2- (5-cyanopentyl) imidazolium, 1- (2-methoxy) Ethyl) -2- (6-cyanohexyl) imidazolium, 1- (3-methoxypropyl) -2-cyanomethylimidazolium, 1- (3-methoxypropyl) -2- (2-cyanoethyl) imidazolium, 1 -(3-methoxypropyl) -2- (3-cyanopropyl) imidazolium, 1- (3-methoxypropyl) -2- (4-cyanobutyl) Dazoriumu, 1- (4-methoxybutyl) -2-cyano-methylimidazolium, 1- (4-methoxybutyl) -2- (2-cyanoethyl) imidazolium,

1- (4-methoxybutyl) -2- (3-cyanopropyl) imidazolium, 1- (4-methoxybutyl) -2- (4-cyanobutyl) imidazolium, 1-ethoxymethyl-2-cyanomethylimidazolium 1-ethoxymethyl-2- (2-cyanoethyl) imidazolium, 1-ethoxymethyl-2- (3-cyanopropyl) imidazolium, 1-ethoxymethyl-2- (4-cyanobutyl) imidazolium, 1-ethoxy Methyl-2- (5-cyanopentyl) imidazolium, 1-ethoxymethyl-2- (6-cyanohexyl) imidazolium, 1- (2-ethoxyethyl) -2-cyanomethylimidazolium, 1- (2- Ethoxyethyl) -2- (2-cyanoethyl) imidazolium, 1- (2-ethoxyethyl) -2- (3-sia Propyl) imidazolium, 1- (2-ethoxyethyl) -2- (5-cyanobutyl) imidazolium, 1- (2-ethoxyethyl) -2- (5-cyanopentyl) imidazolium, 1- (2-ethoxy) Ethyl) -2- (6-cyanohexyl) imidazolium, 1- (3-ethoxypropyl) -2-cyanomethylimidazolium, 1- (3-ethoxypropyl) -2- (2-cyanoethyl) imidazolium, 1 -(3-Ethoxypropyl) -2- (3-cyanopropyl) imidazolium, 1- (3-Ethoxypropyl) -2- (4-cyanobutyl) imidazolium, 1- (4-Ethoxybutyl) -2-cyano Methyl imidazolium, 1- (4-ethoxybutyl) -2- (2-cyanoethyl) imidazolium,

1- (4-ethoxybutyl) -2- (3-cyanopropyl) imidazolium, 1- (4-ethoxybutyl) -2- (4-cyanobutyl) imidazolium, 1-propoxymethyl-2-cyanomethylimidazolium 1-propoxymethyl-2- (2-cyanoethyl) imidazolium, 1-propoxymethyl-2- (3-cyanopropyl) imidazolium, 1-propoxymethyl-2- (4-cyanobutyl) imidazolium, 1-propoxy Methyl-2- (5-cyanopentyl) imidazolium, 1-propoxymethyl-2- (6-cyanohexyl) imidazolium, 1- (2-propoxyethyl) -2-cyanomethylimidazolium,

1- (2-propoxyethyl) -2- (2-cyanoethyl) imidazolium, 1- (2-propoxyethyl) -2- (3-cyanopropyl) imidazolium, 1- (2-propoxyethyl) -2- (4-cyanobutyl) imidazolium, 1- (2-propoxyethyl) -2- (5-cyanopentyl) imidazolium, 1- (2-propoxyethyl) -2- (6-cyanohexyl) imidazolium, 1- (3-propoxypropyl) -2-cyanomethylimidazolium, 1- (3-propoxypropyl) -2- (2-cyanoethyl) imidazolium, 1- (3-propoxypropyl) -2- (3-cyanopropyl) Imidazolium, 1- (3-propoxypropyl) -2- (4-cyanobutyl) imidazolium, 1-methylthiomethyl-2-methyl Louis imidazolium, 1- (2-methylthioethyl) -2-methylimidazolium, 1- (3-methylthiopropyl) -2-methylimidazolium, 1- (4-methylthiobutyl) -2-methylimidazolium, 1 -Ethylthiomethyl-2-methylimidazolium, 1- (2-ethylthioethyl) -2-methylimidazolium, 1- (3-ethylthiopropyl) -2-methylimidazolium, 1- (4-ethylthio) Butyl) -2-methylimidazolium, 1-methylthiomethyl-2-ethylimidazolium, 1- (2-methylthioethyl) -2-ethylimidazolium, 1- (3-methylthiopropyl) -2-ethylimidazolium,

1-ethylthiomethyl-2-ethylimidazolium, 1- (2-ethylthioethyl) -2-ethylimidazolium, 1- (3-ethylthiopropyl) -2-ethylimidazolium, 1- (4-ethyl Thiobutyl) -2-ethylimidazolium, 1-propylthiomethyl-2-ethylimidazolium, 1- (2-propylthioethyl) -2-ethylimidazolium, 1- (3-propylthiopropyl) -2- Ethylimidazolium, 1-methylthiomethyl-2-propylimidazolium, 1- (2-methylthioethyl) -2-propylimidazolium, 1- (3-methylthiopropyl) -2-propylimidazolium, 1-ethylthiomethyl 2-propylimidazolium, 1- (2-ethylthioethyl) -2-propylimidazolium, 1- 3-ethylthiopropyl) -2-propylimidazolium, 1- (4-ethylthiobutyl) -2-propylimidazolium, 1-propylthiomethyl-2-propylimidazolium, 1- (2-propylthioethyl) 2-propylimidazolium,

1- (3-propylthiopropyl) -2-propylimidazolium, 1-methylthiomethyl-2-butylimidazolium, 1- (2-methylthioethyl) -2-butylimidazolium, 1- (3-methylthiopropyl) 2-butylimidazolium, 1-ethylthiomethyl-2-butylimidazolium, 1- (2-ethylthioethyl) -2-butylimidazolium, 1- (3-ethylthiopropyl) -2-butylimidazolium 1-propylthiomethyl-2-butylimidazolium, 1- (2-propylthioethyl) -2-butylimidazolium, 1- (3-propylthiopropyl) -2-butylimidazolium, 1-methylthiomethyl- 2-pentylimidazolium, 1- (2-methylthioethyl) -2-pentylimidazolium, 1- 3-methylthiopropyl) -2-pentylimidazolium, 1-ethylthiomethyl-2-pentylimidazolium, 1- (2-ethylthioethyl) -2-pentylimidazolium, 1-methylthiomethyl-2-hexylimidazolium 1- (2-methylthioethyl) -2-hexylimidazolium, 1-ethylthiomethyl-2-hexylimidazolium, 1- (2-ethylthioethyl) -2-hexylimidazolium, 1-methylthiomethyl-2 -Methoxymethylimidazolium, 1-methylthiomethyl-2- (2-methoxyethyl) imidazolium, 1-methylthiomethyl-2- (3-methoxypropyl) imidazolium, 1-methylthiomethyl-2-ethoxymethylimidazolium, 1-methylthiomethyl-2- (2-ethoxyethyl) ) Imidazolium, 1- (2-methylthioethyl) -2-methoxy-methylimidazolium,

1- (2-methylthioethyl) -2- (2-methoxyethyl) imidazolium, 1- (2-methylthioethyl) -2- (2-ethoxyethyl) imidazolium, 1- (2-ethylthioethyl)- 2-methoxymethylimidazolium, 1- (2-ethylthioethyl) -2- (2-methoxyethyl) imidazolium, 1- (2-ethylthioethyl) -2- (2-ethoxyethyl) imidazolium, 1 -(3-methylthiopropyl) -2-methoxymethylimidazolium, 1- (3-methylthiopropyl) -2- (2-methoxyethyl) imidazolium, 1- (3-methylthiopropyl) -2- (2-ethoxy Ethyl) imidazolium, 1-propylthiomethyl-2-methoxymethylimidazolium, 1-propylthiomethyl-2- (2-methoxy) Til) imidazolium, 1,2-bis (methylthiomethyl) imidazolium, 1-methylthiomethyl-2- (2-methylthioethyl) imidazolium, 1-methylthiomethyl-2-ethylthiomethylimidazolium, 1-methylthiomethyl 2- (2-ethylthioethyl) imidazolium, 1- (2-methylthioethyl) -2-methylthiomethylimidazolium, 1,2-bis (2-methylthioethyl) imidazolium, 1- (2-methylthioethyl) ) -2-ethylthiomethylimidazolium, imidazolium, 1- (2-methylthioethyl) -2- (2-ethylthioethyl) imidazolium, 1- (2-ethylthioethyl) 2-methylthiomethylimidazolium, 1- (2-ethylthioethyl) 2- (2-methylthioethyl) imidazoli 1,2-bis (2-ethylthioethyl) imidazolium, 1-methylthiomethyl-2-cyanomethylimidazolium, 1- (2-methylthioethyl) -2-cyanomethylimidazolium, 1- (3- Methylthiopropyl) -2-cyanomethylimidazolium,

1- (4-methylthiobutyl) -2-cyanomethylimidazolium, 1-ethylthiomethyl-2-cyanomethylimidazolium, 1- (2-ethylthioethyl) -2-cyanomethylimidazolium, 1- (3 -Ethylthiopropyl) -2-cyanomethylimidazolium, 1- (4-ethylthiobutyl) -2-cyanomethylimidazolium, 1-methylthiomethyl-2- (2-cyanoethyl) imidazolium, 1- (2- Methylthioethyl) -2- (2-cyanoethyl) imidazolium, 1- (3-methylthiopropyl) -2- (2-cyanoethyl) imidazolium, 1-ethylthiomethyl-2- (2-cyanoethyl) imidazolium, 1 -(2-ethylthioethyl) -2- (2-cyanoethyl) imidazolium, 1- (3-ethylthiopropiyl) ) -2- (2-cyanoethyl) imidazolium, 1- (4-ethylthiobutyl) -2- (2-cyanoethyl) imidazolium, 1-propylthiomethyl-2- (2-cyanoethyl) imidazolium, 1- (2-propylthioethyl) -2- (2-cyanoethyl) imidazolium, 1- (3-propylthiopropyl) -2- (2-cyanoethyl) imidazolium, 1-methylthiomethyl-2- (3-cyanopropyl) ) Imidazolium, 1- (2-methylthioethyl) -2- (3-cyanopropyl) imidazolium, 1- (3-methylthiopropyl) -2- (3-cyanopropyl) imidazolium, 1-ethylthiomethyl- 2- (3-Cyanopropyl) imidazolium, 1- (2-ethylthioethyl) -2- (3-cyanopropyl) imidazoli Arm, 1- (3-ethyl thio propyl) -2- (3-cyanopropyl) imidazolium,

1- (4-ethylthiobutyl) -2- (3-cyanopropyl) imidazolium, 1-propylthiomethyl-2- (3-cyanopropyl) imidazolium, 1- (2-propylthioethyl) -2- (3-cyanopropyl) imidazolium, 1- (3-propylthiopropyl) -2- (3-cyanopropyl) imidazolium, 1-methylthiomethyl-2- (4-cyanobutyl) imidazolium, 1- (2- Methylthioethyl) -2- (4-cyanobutyl) imidazolium, 1- (3-methylthiopropyl) -2- (4-cyanobutyl) imidazolium, 1-ethylthiomethyl-2- (4-cyanobutyl) imidazolium, 1 -(2-ethylthioethyl) -2- (4-cyanobutyl) imidazolium, 1- (3-ethylthiopropyl) -2- (4- Anobutyl) imidazolium, 1-propylthiomethyl-2- (4-cyanobutyl) imidazolium, 1- (2-propylthioethyl) -2- (4-cyanobutyl) imidazolium, 1- (3-propylthiopropyl) 2- (4-cyanobutyl) imidazolium, 1-methylthiomethyl-2- (5-cyanopentyl) imidazolium, 1- (2-methylthioethyl) -2- (5-cyanopentyl) imidazolium, 1- ( 3-methylthiopropyl) -2- (5-cyanopentyl) imidazolium, 1-ethylthiomethyl-2- (5-cyanopentyl) imidazolium, 1- (2-ethylthioethyl) -2- (5-cyano Pentyl) imidazolium, 1-methylthiomethyl-2- (6-cyanohexyl) imidazolium, 1- (2-methyl) Oethyl) -2- (6-cyanohexyl) imidazolium, 1-ethylthiomethyl-2- (6-cyanohexyl) imidazolium, 1- (2-ethylthioethyl) -2- (6-cyanohexyl) imidazole Lithium, 1-cyanomethyl-2-methylimidazolium, 1-dicyanomethyl-2-methylimidazolium, 1- (2-cyanoethyl) -2-methylimidazolium, 1- (2,3-dicyanoethyl) -2- Methyl imidazolium,

1- (3-cyanopropyl) -2-methylimidazolium, 1- (2,3-dicyanopropyl) -2-methylimidazolium, 1- (4-cyanobutyl) -2-methylimidazolium, 1- (3 -Cyanopentyl) -2-methylimidazolium, 1- (6-cyanohexyl) -2-methylimidazolium, 1-cyanomethyl-2-ethylimidazolium, 1-dicyanomethyl-2-ethylimidazolium, 1- ( 2-cyanoethyl) -2-ethylimidazolium, 1- (2,3-dicyanoethyl) -2-ethylimidazolium, 1- (3-cyanopropyl) -2-ethylimidazolium, 1- (2,3- Dicyanopropyl) -2-ethylimidazolium, 1- (4-cyanobutyl) -2-ethylimidazolium, 1- (5-cyanopentyl) 2-ethylimidazolium, 1- (6-cyanohexyl) -2-ethylimidazolium, 1-cyanomethyl-2-propylimidazolium, 1-dicyanomethyl-2-propylimidazolium, 1- (2-cyanoethyl)- 2-propylimidazolium, 1- (2,3-dicyanoethyl) -2-propylimidazolium, 1- (3-cyanopropyl) -2-propylimidazolium, 1- (2,3-dicyanopropyl) -2 -Propylimidazolium, 1- (4-cyanobutyl) -2-propylimidazolium, 1-cyanomethyl-2-butylimidazolium, 1- (2-cyanoethyl) -2-butylimidazolium, 1- (3-cyanopropyl ) -2-Butylimidazolium, 1- (4-cyanobutyl) -2-butylimidazolium, 1 Cyanomethyl-2-methoxymethylimidazolium, 1- (2-cyanoethyl) -2-methoxymethylimidazolium, 1- (3-cyanopropyl) -2-methoxymethylimidazolium, 1- (4-cyanobutyl) -2- Methoxymethylimidazolium, 1- (5-cyanopentyl) -2-methoxymethylimidazolium, 1- (6-cyanohexyl) -2-methoxymethylimidazolium, 1-cyanomethyl-2- (2-methoxyethyl) imidazole 1- (2-cyanoethyl) -2- (2-methoxyethyl) imidazolium, 1- (3-cyanopropyl) -2- (2-methoxyethyl) imidazolium,

1- (4-cyanobutyl) -2- (2-methoxyethyl) imidazolium, 1- (5-cyanopentyl) -2- (2-methoxyethyl) imidazolium, 1- (6-cyanohexyl) -2- (2-methoxyethyl) imidazolium, 1-cyanomethyl-2- (3-methoxypropyl) imidazolium, 1- (2-cyanoethyl) -2- (3-methoxypropyl) imidazolium, 1- (3-cyanopropyl ) -2- (3-methoxypropyl) imidazolium, 1- (4-cyanobutyl) -2- (3-methoxypropyl) imidazolium, 1-cyanomethyl-2- (4-methoxybutyl) imidazolium, 1- ( 2-cyanoethyl) -2- (4-methoxybutyl) imidazolium, 1- (3-cyanopropyl) -2- (4-methoxybutyl) Dazolium, 1- (4-cyanobutyl) -2- (4-methoxybutyl) imidazolium, 1-cyanomethyl-2-ethoxymethylimidazolium, 1- (2-cyanoethyl) -2-ethoxymethylimidazolium, 1- ( 3-cyanopropyl) -2-ethoxymethylimidazolium, 1- (4-cyanobutyl) -2-ethoxymethylimidazolium, 1- (5-cyanopentyl) -2-ethoxymethylimidazolium, 1- (6-cyano Hexyl) -2-ethoxymethylimidazolium, 1-cyanomethyl-2- (2-ethoxyethyl) imidazolium, 1- (2-cyanoethyl) -2- (2-ethoxyethyl) imidazolium, 1- (3-cyano Propyl) -2- (2-ethoxyethyl) imidazolium, 1- (3-cyanobutyl) -2 (2-ethoxyethyl) imidazolium, 1- (5-cyanopentyl) -2- (2-ethoxyethyl) imidazolium, 1- (6-cyanohexyl) -2- (2-ethoxyethyl) imidazolium, 1 -Cyanomethyl-2- (3-ethoxypropyl) imidazolium,

1- (2-cyanoethyl) -2- (3-ethoxypropyl) imidazolium, 1- (3-cyanopropyl) -2- (3-ethoxypropyl) imidazolium, 1- (4-cyanobutyl) -2- ( 3-Ethoxypropyl) imidazolium, 1-cyanomethyl-2- (4-ethoxybutyl) imidazolium, 1- (2-cyanoethyl) -2- (4-ethoxybutyl) imidazolium, 1- (3-cyanopropyl) 2- (4-ethoxybutyl) imidazolium, 1- (4-cyanobutyl) -2- (4-ethoxybutyl) imidazolium, 1-cyanomethyl-2-propoxymethylimidazolium, 1- (2-cyanoethyl)- 2-propoxymethylimidazolium, 1- (3-cyanopropyl) -2-propoxymethylimidazolium, 1- (4 Cyanobutyl) -2-propoxymethylimidazolium, 1- (5-cyanopentyl) -2-propoxymethylimidazolium, 1- (6-cyanohexyl) -2-propoxymethylimidazolium, 1-cyanomethyl-2- (2 -Propoxyethyl) imidazolium, 1- (2-cyanoethyl) -2- (2-propoxyethyl) imidazolium, 1- (3-cyanopropyl) -2- (2-propoxyethyl) imidazolium, 1- (4 -Cyanobutyl) -2- (2-propoxyethyl) imidazolium, 1- (5-cyanopentyl) -2- (2-propoxyethyl) imidazolium, 1- (6-cyanohexyl) -2- (2-propoxy) Ethyl) imidazolium, 1-cyanomethyl-2- (3-propoxypropyl) imidazolium, 1 (2-cyanoethyl) -2- (3-propoxypropyl) imidazolium, 1- (3-cyanopropyl) -2- (3-propoxypropyl) imidazolium, 1- (4-cyanobutyl) -2- (3- Propoxypropyl) imidazolium, 1-cyanomethyl-2-methylthiomethylimidazolium, 1- (2-cyanoethyl) -2-methylthiomethylimidazolium, 1- (3-cyanopropyl) -2-methylthiomethylimidazolium,

1- (4-cyanobutyl) -2-methylthiomethylimidazolium, 1- (5-cyanopentyl) -2-methylthiomethylimidazolium, 1- (6-cyanohexyl) -2-methylthiomethylimidazolium, 1-cyanomethyl 2- (2-methylthioethyl) imidazolium, 1- (2-cyanoethyl) -2- (2-methylthioethyl) imidazolium, 1- (3-cyanopropyl) -2- (2-methylthioethyl) imidazolium 1- (4-cyanobutyl) -2- (2-methylthioethyl) imidazolium, 1- (5-cyanopentyl) -2- (2-methylthioethyl) imidazolium, 1- (6-cyanohexyl) -2 -(2-methylthioethyl) imidazolium, 1-cyanomethyl-2- (3-methylthiopropyl) imidazoli 1- (2-cyanoethyl) -2- (3-methylthiopropyl) imidazolium, 1- (3-cyanopropyl) -2- (3-methylthiopropyl) imidazolium, 1- (4-cyanobutyl) -2 -(3-methylthiopropyl) imidazolium, 1-cyanomethyl-2- (4-methylthiobutyl) imidazolium, 1- (2-cyanoethyl) -2- (4-methylthiobutyl) imidazolium, 1- (3-cyano Propyl) -2- (4-methylthiobutyl) imidazolium, 1- (4-cyanobutyl) -2- (4-methylthiobutyl) imidazolium, 1-cyanomethyl-2-ethylthiomethylimidazolium, 1- (2- Cyanoethyl) -2-ethylthiomethylimidazolium, 1- (3-cyanopropyl) -2-ethylthiomethylimid Zolium, 1- (4-cyanobutyl) -2-ethylthiomethylimidazolium, 1- (5-cyanopentyl) -2-ethylthiomethylimidazolium, 1- (6-cyanohexyl) -2-ethylthiomethylimidazole 1- (3-cyanopropyl) -2- (1-cyanomethyl-2- (2-ethylthioethyl) imidazolium, 1- (2-cyanoethyl) -2- (2-ethylthioethyl) imidazolium, 2-ethylthioethyl) imidazolium,

1- (3-cyanobutyl) -2- (2-ethylthioethyl) imidazolium, 1- (5-cyanopentyl) -2- (2-ethylthioethyl) imidazolium, 1- (6-cyanohexyl)- 2- (2-ethylthioethyl) imidazolium, 1-cyanomethyl-2- (3-ethylthiopropyl) imidazolium, 1- (2-cyanoethyl) -2- (3-ethylthiopropyl) imidazolium, 1- (3-cyanopropyl) -2- (3-ethylthiopropyl) imidazolium, 1- (4-cyanobutyl) -2- (3-ethylthiopropyl) imidazolium, 1-cyanomethyl-2- (4-ethylthio) Butyl) imidazolium, 1- (2-cyanoethyl) -2- (4-ethylthiobutyl) imidazolium, 1- (3-cyanopropyl) -2- (4- Tilthiobutyl) imidazolium, 1- (4-cyanobutyl) -2- (4-ethylthiobutyl) imidazolium, 1-cyanomethyl-2-propylthiomethylimidazolium, 1- (2-cyanoethyl) -2-propylthiomethyl Imidazolium, 1- (3-cyanopropyl) -2-propylthiomethylimidazolium, 1- (4-cyanobutyl) -2-propylthiomethylimidazolium, 1- (5-cyanopentyl) -2-propylthiomethyl Imidazolium, 1- (6-cyanohexyl) -2-propylthiomethylimidazolium, 1-cyanomethyl-2- (2-propylthioethyl) imidazolium, 1- (2-cyanoethyl) -2- (2-propyl) Thioethyl) imidazolium, 1- (3-cyanopropyl) -2- (2-propiyl) Thioethyl) imidazolium, 1- (4-cyanobutyl) -2- (2-propylthioethyl) imidazolium, 1- (5-cyanopentyl) -2- (2-propylthioethyl) imidazolium, 1- (6 -Cyanohexyl) -2- (2-propylthioethyl) imidazolium,

1-cyanomethyl-2- (3-propylthiopropyl) imidazolium, 1- (2-cyanoethyl) -2- (3-propylthiopropyl) imidazolium, 1- (3-cyanopropyl) -2- (3- Propylthiopropyl) imidazolium, 1- (4-cyanobutyl) -2- (3-propylthiopropyl) imidazolium, 1,2-bis (cyanomethyl) imidazolium, 1-cyanomethyl-2- (2-cyanoethyl) imidazo 1-cyanomethyl-2- (3-cyanopropyl) imidazolium, 1-cyanomethyl-2- (4-cyanobutyl) imidazolium, 1-cyanomethyl-2- (5-cyanopentyl) imidazolium, 1-cyanomethyl- 2- (6-Cyanohexyl) imidazolium, 1- (2-cyanoethyl) -2-cyano Tyrimidazolium, 1,2-bis (2-cyanoethyl) imidazolium, 1- (2-cyanoethyl) -2- (3-cyanopropyl) imidazolium, 1- (2-cyanoethyl) -2- (4-cyanobutyl) ) Imidazolium, 1- (2-cyanoethyl) -2- (5-cyanopentyl) imidazolium,

1- (2-cyanoethyl) -2- (6-cyanohexyl) imidazolium, 1- (3-cyanopropyl) -2-cyanomethylimidazolium, 1- (3-cyanopropyl) -2- (2-cyanoethyl) ) Imidazolium, 1,2-bis (3-cyanopropyl) imidazolium, 1- (3-cyanopropyl) -2- (4-cyanobutyl) imidazolium, 1- (4-cyanobutyl) -2-cyanomethylimidazole 1- (4-cyanobutyl) -2- (2-cyanoethyl) imidazolium, 1- (4-cyanobutyl) -2- (3-cyanopropyl) imidazolium, 1,2-bis (4-cyanobutyl) imidazole 1- (5-cyanopentyl) -2-cyanomethylimidazolium, 1- (5-cyanopentyl) -2- (2-cyanoethyl) Midazoriumu, 1- (6-cyano-hexyl) -2-cyano-methylimidazolium, 1- (6-cyano-hexyl) -2- (2-cyanoethyl) include imidazolium and imidazolium. These N, C-2 substituted imidazoliums all have asymmetric structures.

  Examples of the N, N, C-3 substituted imidazolium cation include 1,2,3-trimethylimidazolium, 1,3-dimethyl-2-ethylimidazolium, and 1,3-diethyl-2-methyl. Imidazolium, 1,2,3-triethylimidazolium, 1,3-dipropyl-2-methylimidazolium, 1,3-dipropyl-2-ethylimidazolium, 1,3-dibutyl-2methylimidazolium, 1, 3-dibutyl-2-ethylimidazolium, 1,3-bis (methoxymethyl) -2-methylimidazolium, 1,3-bis (methoxymethyl) -2-ethylimidazolium, 1,3-bis (2-methoxy) Ethyl) -2-methylimidazolium, 1,3-bis (2-methoxyethyl) -2-ethylimidazolium, 1,3-bis (ethoxy) Til) -2-methylimidazolium, 1,3-bis (ethoxymethyl) -2-ethylimidazolium, 1,3-bis (2-ethoxyethyl) -2-methylimidazolium, 1,3-bis (2 -Ethoxyethyl) -2-ethylimidazolium, 1,3-bis (methylthiomethyl) -2-methylimidazolium, 1,3-bis (methylthiomethyl) -2-ethylimidazolium, 1,3-bis (2 -Methylthioethyl) -2-methylimidazolium, 1,3-bis (2-methylthioethyl) -2-ethylimidazolium,

1,3-bis (ethylthiomethyl) -2-methylimidazolium, 1,3-bis (ethylthiomethyl) -2-ethylimidazolium, 1,3-bis (2-ethylthioethyl) -2-methyl Imidazolium, 1,3-bis (2-ethylthioethyl) -2-ethylimidazolium, 1,3-bis (cyanomethyl) -2-methylimidazolium, 1,3-bis (cyanomethyl) -2-ethylimidazo 1,3-bis (2-cyanoethyl) -2-methylimidazolium, 1,3-bis (2-cyanoethyl) -2-ethylimidazolium, 1,3-bis (3-cyanopropyl) -2- Methylimidazolium, 1,3-bis (3-cyanopropyl) -2-ethylimidazolium, 1,3-bis (4-cyanobutyl) -2-methylimidazolium, 1 3- bis (4-cyanobutyl) N having a symmetrical structure such as 2-ethyl imidazolium, N, C-3 substituted imidazolium;

1,2-dimethyl-3-ethylimidazolium, 1-methyl-2-ethyl-3-ethylimidazolium, 1,2-dimethyl-3-propylimidazolium, 1-methyl-2-ethyl-3-propylimidazolium 1,2-dimethyl-3-butylimidazolium, 1-methyl-2-ethyl-3-butylimidazolium, 1,2-dimethyl-3-propylimidazolium, 1-methyl-2-ethyl-3- Propylimidazolium, 1,2-dimethyl-3-butylimidazolium, 1-methyl-2-ethyl-3-butylimidazolium, 1-ethyl-2-methyl-3-propylimidazolium, 1,2-diethyl- 3-propylimidazolium, 1-ethyl-2-methyl-3-butylimidazolium, 1,2-diethyl-3-butylimidazolium 1-propyl-2-methyl-3-butylimidazolium, 1-propyl-2-ethyl-3-butylimidazolium, 1,2-dimethyl-3-methoxymethylimidazolium, 1-methyl-2-ethyl- 3-methoxymethylimidazolium, 1,2-dimethyl-3- (2-methoxyethyl) imidazolium, 1-methyl-2-ethyl-3- (2-methoxyethyl) imidazolium, 1,2-dimethyl-3 -(3-methoxypropyl) imidazolium, 1-methyl-2-ethyl-3- (3-methoxypropyl) imidazolium, 1,2-dimethyl-3- (4-methoxybutyl) imidazolium, 1-methyl- 2-ethyl-3- (4-methoxybutyl) imidazolium, 1,2-dimethyl-3-ethoxymethylimidazolium, 1-methyl-2 Ethyl-3-ethoxymethylimidazolium, 1,2-dimethyl-3- (2-ethoxyethyl) imidazolium, 1-methyl-2-ethyl-3- (2-ethoxyethyl) imidazolium, 1,2-dimethyl -3- (3-ethoxypropyl) imidazolium,

1-methyl-2-ethyl-3- (3-ethoxypropyl) imidazolium, 1,2-dimethyl-3- (4-ethoxybutyl) imidazolium, 1-methyl-2-ethyl-3- (4-ethoxy Butyl) imidazolium, 1-ethyl-2-methyl-3-methoxymethylimidazolium, 1,2-diethyl-3-methoxymethylimidazolium, 1-ethyl-2-methyl-3- (2-methoxyethyl) imidazole 1,2-diethyl-3- (2-methoxyethyl) imidazolium, 1-ethyl-2-methyl-3- (3-methoxypropyl) imidazolium, 1,2-diethyl-3- (3-methoxy) Propyl) imidazolium, 1-ethyl-2-methyl-3-ethoxymethylimidazolium, 1,2-diethyl-3-ethoxymethylimidazolium 1-ethyl-2-methyl-3- (2-ethoxyethyl) imidazolium, 1,2-diethyl-3- (2-ethoxyethyl) imidazolium, 1-ethyl-2-methyl-3- (3- Ethoxypropyl) imidazolium, 1,2-diethyl-3- (3-ethoxypropyl) imidazolium, 1-ethyl-2-methyl-3- (4-ethoxybutyl) imidazolium, 1,2-diethyl-3- (4-Ethoxybutyl) imidazolium, 1-ethyl-2-methyl-3-propoxymethylimidazolium, 1,2-diethyl-3-propoxymethylimidazolium, 1-ethyl-2-methyl-3- (2- Propoxyethyl) imidazolium, 1,2-diethyl-3- (2-propoxyethyl) imidazolium, 1-ethyl-2-methyl-3- (3-propyl Pokishipuropiru) imidazolium, 1,2-diethyl-3- (3-propoxy-propyl) imidazolium, 1-propyl-2-methyl-3-methoxy-methylimidazolium,

1-propyl-2-ethyl-3-methoxymethylimidazolium, 1-propyl-2-methyl-3- (2-methoxyethyl) imidazolium, 1-propyl-2-ethyl-3- (2-methoxyethyl) Imidazolium, 1-propyl-2-methyl-3- (3-methoxypropyl) imidazolium, 1-propyl-2-ethyl-3- (3-methoxypropyl) imidazolium, 1-propyl-2-methyl-3 -Ethoxymethylimidazolium, 1-propyl-2-ethyl-3-ethoxymethylimidazolium, 1-propyl-2-methyl-3- (2-ethoxyethyl) imidazolium, 1-propyl-2-ethyl-3- (2-ethoxyethyl) imidazolium, 1-propyl-2-methyl-3- (3-ethoxypropyl) imidazolium, Propyl-2-ethyl-3- (3-ethoxypropyl) imidazolium, 1-propyl-2-methyl-3-propoxymethylimidazolium, 1-propyl-2-ethyl-3-propoxymethylimidazolium, 1-propyl 2-methyl-3- (2-propoxyethyl) imidazolium, 1-propyl-2-ethyl-3- (2-propoxyethyl) imidazolium, 1-propyl-2-methyl-3- (3-propoxypropyl) ) Imidazolium, 1-propyl-2-ethyl-3- (3-propoxypropyl) imidazolium, 1-butyl-2-methyl-3-methoxymethylimidazolium, 1-butyl-2-ethyl-3-methoxymethyl Imidazolium,

1-butyl-2-methyl-3- (2-methoxyethyl) imidazolium, 1-butyl-2-ethyl-3- (2-methoxyethyl) imidazolium, 1-butyl-2-methyl-3- (3 -Methoxypropyl) imidazolium, 1-butyl-2-ethyl-3- (3-methoxypropyl) imidazolium, 1-butyl-2-methyl-3-ethoxymethylimidazolium, 1-butyl-2-ethyl-3 -Ethoxymethylimidazolium, 1-butyl-2-methyl-3- (2-ethoxyethyl) imidazolium, 1-butyl-2-ethyl-3- (2-ethoxyethyl) imidazolium, 1-butyl-2- Methyl-3-propoxymethylimidazolium, 1-butyl-2-ethyl-3-propoxymethylimidazolium, 1,2-dimethyl-3-methylthio Methylimidazolium, 1-methyl-2-ethyl-3-methylthiomethylimidazolium, 1,2-dimethyl-3- (2-methylthioethyl) imidazolium, 1-methyl-2-ethyl-3- (2-methylthio) Ethyl) imidazolium, 1,2-dimethyl-3- (3-methylthiopropyl) imidazolium, 1-methyl-2-ethyl-3- (3-methylthiopropyl) imidazolium, 1,2-dimethyl-3- ( 4-methylthiobutyl) imidazolium, 1-methyl-2-ethyl-3- (4-methylthiobutyl) imidazolium, 1,2-dimethyl-3-ethylthiomethylimidazolium, 1,2-dimethyl-3-ethyl Thiomethylimidazolium,

1-methyl-2-ethyl-3- (2-ethylthioethyl) imidazolium, 1,2-dimethyl-3- (3-ethylthiopropyl) imidazolium, 1-methyl-2-ethyl-3- (3 -Ethylthiopropyl) imidazolium, 1,2-dimethyl-3- (4-ethylthiobutyl) imidazolium, 1-methyl-2-ethyl-3- (4-ethylthiobutyl) imidazolium, 1-ethyl- 2-methyl-3- (methylthiomethyl) imidazolium, 1,2-diethyl-3- (methylthiomethyl) imidazolium, 1-ethyl-2-methyl-3- (2-methylthioethyl) imidazolium, 1,2 -Diethyl-3- (2-methylthioethyl) imidazolium, 1-ethyl-2-methyl-3- (3-methylthiopropyl) imidazolium, 1,2-die Ru-3- (3-methylthiopropyl) imidazolium, 1-ethyl-2-methyl-3-ethylthiomethylimidazolium, 1,2-diethyl-3-ethylthiomethylimidazolium, 1-ethyl-2-methyl -3- (2-ethylthioethyl) imidazolium, 1,2-diethyl-3- (2-ethylthioethyl) imidazolium, 1-ethyl-2-methyl-3- (3-ethylthiopropyl) imidazolium 1,2-diethyl-3- (3-ethylthiopropyl) imidazolium, 1-ethyl-2-methyl-3- (4-ethylthiobutyl) imidazolium,

1,2-diethyl-3- (4-ethylthiobutyl) imidazolium, 1-ethyl-2-methyl-3-propylthiomethylimidazolium, 1,2-diethyl-3-propylthiomethylimidazolium, 1- Ethyl-2-methyl-3- (2-propylthioethyl) imidazolium, 1,2-diethyl-3- (2-propylthioethyl) imidazolium, 1-ethyl-2-methyl-3- (3-propyl) Thiopropyl) imidazolium, 1,2-diethyl-3- (3-propylthiopropyl) imidazolium, 1-propyl-2-methyl-3-methylthiomethylimidazolium, 1-propyl-2-ethyl-3-methylthio Methyl imidazolium, 1-propyl-2-methyl-3- (2-methylthioethyl) imidazolium, 1-propyl-2-ethyl Ru-3- (2-methylthioethyl) imidazolium, 1-propyl-2-methyl-3- (3-methylthiopropyl) imidazolium, 1-propyl-2-ethyl-3- (3-methylthiopropyl) imidazolium 1-propyl-2-methyl-3-ethylthiomethylimidazolium, 1-propyl-2-ethyl-3-ethylthiomethylimidazolium, 1-propyl-2-methyl-3- (2-ethylthioethyl) Imidazolium, 1-propyl-2-ethyl-3- (2-ethylthioethyl) imidazolium, 1-propyl-2-methyl-3- (3-ethylthiopropyl) imidazolium, 1-propyl-2-ethyl -3- (3-ethylthiopropyl) imidazolium, 1-propyl-2-methyl-3-propylthiomethylimidazolium,

1-propyl-2-ethyl-3-propylthiomethylimidazolium, 1-propyl-2-methyl-3- (2-propylthioethyl) imidazolium, 1-propyl-2-ethyl-3- (2-propyl) Thioethyl) imidazolium, 1-butyl-2-methyl-3-methylthiomethylimidazolium, 1-butyl-2-ethyl-3-methylthiomethylimidazolium, 1-butyl-2-methyl-3- (2-methylthio) Ethyl) imidazolium, 1-butyl-2-ethyl-3- (2-methylthioethyl) imidazolium, 1-butyl-2-methyl-3- (3-methylthiopropyl) imidazolium, 1-butyl-2-ethyl -3- (3-methylthiopropyl) imidazolium, 1-butyl-2-methyl-3-ethylthiomethylimidazolium, 1 Butyl-2-ethyl-3-ethylthiomethylimidazolium, 1-butyl-2-methyl-3- (2-ethylthioethyl) imidazolium, 1-butyl-2-ethyl-3- (2-ethylthioethyl) ) Imidazolium, 1-butyl-2-methyl-3-propylthiomethylimidazolium, 1-butyl-2-ethyl-3-propylthiomethylimidazolium, 1-butyl-2-methyl-3- (2-propyl) Thioethyl) imidazolium, 1-butyl-2-ethyl-3- (2-propylthioethyl) imidazolium, 1-pentyl-2-methyl-3-methylthiomethylimidazolium, 1-pentyl-2-ethyl-3 -Methylthiomethylimidazolium, 1,2-dimethyl-3-cyanomethylimidazolium, 1-methyl-2-ethyl-3-cyano Chill imidazolium, 1,2-dimethyl-3- (2-cyanoethyl) imidazolium,

1-methyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1,2-dimethyl-3- (3-cyanopropyl) imidazolium, 1-methyl-2-ethyl-3- (3-cyanopropyl) ) Imidazolium, 1,2-dimethyl-3- (4-cyanobutyl) imidazolium, 1-methyl-2-ethyl-3- (4-cyanobutyl) imidazolium, 1,2-dimethyl-3- (5-cyano) Pentyl) imidazolium, 1-methyl-2-ethyl-3- (5-cyanopentyl) imidazolium, 1-ethyl-2-methyl-3-cyanomethylimidazolium, 1,2-diethyl-3-cyanomethylimidazole 1-ethyl-2-methyl-3- (2-cyanoethyl) imidazolium, 1,2-diethyl-3- (2-cyanoethyl) imidazolium, -Ethyl-2-methyl-3- (3-cyanopropyl) imidazolium, 1,2-diethyl-3- (3-cyanopropyl) imidazolium, 1-ethyl-2-methyl-3- (4-cyanobutyl) Imidazolium, 1,2-diethyl-3- (4-cyanobutyl) imidazolium, 1-propyl-2-methyl-3-cyanomethylimidazolium, 1-propyl-2-ethyl-3-cyanomethylimidazolium, 1 -Propyl-2-methyl-3- (2-cyanoethyl) imidazolium, 1-propyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1-propyl-2-methyl-3- (3-cyanopropyl) ) Imidazolium, 1-propyl-2-ethyl-3- (3-cyanopropyl) imidazolium, 1-propyl-2-methyl-3- (4) Cyanobutyl) imidazolium, 1-propyl-2-ethyl-3- (4-cyanobutyl) imidazolium, 1-butyl-2-methyl-3-cyanomethylimidazolium, 1-butyl-2-ethyl-3-cyanomethyl Imidazolium, 1-butyl-2-methyl-3- (2-cyanoethyl) imidazolium, 1-butyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1-butyl-2-methyl-3- ( 3-cyanopropyl) imidazolium,

1-butyl-2-ethyl-3- (3-cyanopropyl) imidazolium, 1,2-dimethyl-3-dicyanomethylimidazolium, 1-methyl-2-ethyl-3-dicyanomethylimidazolium, 1,2 -Dimethyl-3- (2,3-dicyanoethyl) imidazolium, 1-methyl-2-ethyl-3- (2,3-dicyanoethyl) imidazolium, 1,2-dimethyl-3- (2,3- Dicyanopropyl) imidazolium, 1-methyl-2-ethyl-3- (2,3-dicyanopropyl) imidazolium, 1-ethyl-2-methyl-3-dicyanomethylimidazolium, 1,2-diethyl-3- Dicyanomethylimidazolium, 1-ethyl-2-methyl-3- (2,3-dicyanoethyl) imidazolium, 1,2-diethyl-3- (2,3-dicia Ethyl) imidazolium, 1-ethyl-2-methyl-3- (2,3-dicyanopropyl) imidazolium, 1,2-diethyl-3- (2,3-dicyanopropyl) imidazolium, 1-propyl-2 -Methyl-3-dicyanomethylimidazolium, 1-propyl-2-ethyl-3-dicyanomethylimidazolium, 1-propyl-2-methyl-3- (2,3-dicyanoethyl) imidazolium, 1-propyl- 2-ethyl-3- (2,3-dicyanoethyl) imidazolium, 1-propyl-2-methyl-3- (2,3-dicyanopropyl) imidazolium,

1-propyl-2-ethyl-3- (2,3-dicyanopropyl) imidazolium, 1-methoxymethyl-2-methyl-3- (2-methoxyethyl) imidazolium, 1-methoxymethyl-2-ethyl- 3- (2-methoxyethyl) imidazolium, 1-methoxymethyl-2-methyl-3- (2-methoxyethyl) imidazolium, 1-methoxymethyl-2-methyl-3- (2-methoxypropyl) imidazolium 1-methoxymethyl-2-ethyl-3- (2-methoxypropyl) imidazolium, 1- (2-methoxyethyl) -2-methyl-3-ethoxymethylimidazolium, 1- (2-methoxyethyl)- 2-ethyl-3-ethoxymethylimidazolium, 1- (2-methoxyethyl) -2-methyl-3- (3-methoxypropyl) Dazolium, 1- (2-methoxyethyl) -2-ethyl-3- (3-methoxypropyl) imidazolium, 1- (2-methoxyethyl) -2-methyl-3- (2-ethoxyethyl) imidazolium, 1- (2-methoxyethyl) -2-ethyl-3- (2-ethoxyethyl) imidazolium, 1-ethoxymethyl-2-methyl-3- (2-ethoxyethyl) imidazolium, 1-ethoxymethyl-2 -Ethyl-3- (2-ethoxyethyl) imidazolium, 1-ethoxymethyl-2-methyl-3- (2-ethoxypropyl) imidazolium, 1-ethoxymethyl-2-ethyl-3- (2-ethoxypropyl) ) Imidazolium, 1-methoxymethyl-2-methyl-3- (2-methylthiomethyl) imidazolium, 1-methoxymethyl-2-ethyl -3- (2-methylthiomethyl) imidazolium, 1-methoxymethyl-2-methyl-3- (2-methylthioethyl) imidazolium, 1-methoxymethyl-2-ethyl-3- (2-methylthioethyl) imidazole 1-methoxymethyl-2-methyl-3- (2-ethylthioethyl) imidazolium, 1-methoxymethyl-2-ethyl-3- (2-ethylthioethyl) imidazolium,

1- (2-methoxyethyl) -2-methyl-3-methylthiomethylimidazolium, 1- (2-methoxyethyl) -2-ethyl-3-methylthiomethylimidazolium, 1- (2-methoxyethyl) -2 -Methyl-3- (2-methylthioethyl) imidazolium, 1- (2-methoxyethyl) -2-ethyl-3- (2-methylthioethyl) imidazolium, 1- (2-methoxyethyl) -2-methyl -3-ethylthiomethylimidazolium, 1- (2-methoxyethyl) -2-ethyl-3-ethylthiomethylimidazolium, 1- (2-methoxyethyl) -2-methyl-3- (2-ethylthio) Ethyl) imidazolium, 1- (2-methoxyethyl) -2-ethyl-3- (2-ethylthioethyl) imidazolium, 1-ethoxymethyl-2-methyl 3-methylthiomethylimidazolium, 1-ethoxymethyl-2-ethyl-3-methylthiomethylimidazolium, 1-ethoxymethyl-2-methyl-3- (2-methylthioethyl) imidazolium, 1-ethoxymethyl- 2-ethyl-3- (2-methylthioethyl) imidazolium, 1-ethoxymethyl-2-methyl-3-ethylthiomethylimidazolium, 1-ethoxymethyl-2-ethyl-3-ethylthiomethylimidazolium, 1 -Ethoxymethyl-2-methyl-3- (2-ethylthioethyl) imidazolium, 1-ethoxymethyl-2-ethyl-3- (2-ethylthioethyl) imidazolium, 1- (2-ethoxyethyl)- 2-methyl-3-methylthiomethylimidazolium, 1- (2-ethoxyethyl) -2-ethyl- -Methylthiomethylimidazolium, 1- (2-ethoxyethyl) -2-methyl-3- (2-methylthioethyl) imidazolium, 1- (2-ethoxyethyl) -2-ethyl-3- (2-methylthioethyl) ) Imidazolium, 1- (2-ethoxyethyl) -2-methyl-3- (2-ethylthioethyl) imidazolium,

1- (2-ethoxyethyl) -2-ethyl-3- (2-ethylthioethyl) imidazolium, 1-methoxymethyl-2-methyl-3-cyanomethylimidazolium, 1-methoxymethyl-2-ethyl- 3-cyanomethylimidazolium, 1-methoxymethyl-2-methyl-3- (2-cyanoethyl) imidazolium, 1-methoxymethyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1-methoxymethyl- 2-methyl-3- (3-cyanopropyl) imidazolium, 1-methoxymethyl-2-ethyl-3- (3-cyanopropyl) imidazolium, 1-methoxymethyl-2-methyl-3- (4-cyanobutyl) ) Imidazolium, 1-methoxymethyl-2-ethyl-3- (4-cyanobutyl) imidazolium, 1-methoxymethyl 2-methyl-3- (5-cyanopentyl) imidazolium, 1-methoxymethyl-2-ethyl-3- (5-cyanopentyl) imidazolium, 1- (2-methoxyethyl) -2-methyl-3- Cyanomethylimidazolium, 1- (2-methoxyethyl) -2-ethyl-3-cyanomethylimidazolium, 1- (2-methoxyethyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (2-methoxyethyl) -2-ethyl-3- (2-cyanoethyl) imidazolium, 1- (2-methoxyethyl) -2-methyl-3- (3-cyanopropyl) imidazolium,

1- (2-methoxyethyl) -2-ethyl-3- (3-cyanopropyl) imidazolium, 1- (2-methoxyethyl) -2-methyl-3- (4-cyanobutyl) imidazolium, 1- ( 2-methoxyethyl) -2-ethyl-3- (4-cyanobutyl) imidazolium, 1- (3-methoxypropyl) -2-methyl-3-cyanomethylimidazolium, 1- (3-methoxypropyl) -2 -Ethyl-3-cyanomethylimidazolium, 1- (3-methoxypropyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (3-methoxypropyl) -2-ethyl-3- (2 -Cyanoethyl) imidazolium, 1- (3-methoxypropyl) -2-methyl-3- (3-cyanopropyl) imidazolium, 1- (3-methoxypropyl) 2-ethyl-3- (3-cyanopropyl) imidazolium, 1- (4-methoxybutyl) -2-methyl-3-cyanomethylimidazolium, 1- (4-methoxybutyl) -2-ethyl-3- Cyanomethylimidazolium, 1- (4-methoxybutyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (4-methoxybutyl) -2-ethyl-3- (2-cyanoethyl) imidazolium 1-ethoxymethyl-2-methyl-3-cyanomethylimidazolium, 1-ethoxymethyl-2-ethyl-3-cyanomethylimidazolium, 1-ethoxymethyl-2-methyl-3- (2-cyanoethyl) imidazole 1-ethoxymethyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1-ethoxymethyl-2-methyl-3 (3-cyanopropyl) imidazolium, 1-ethoxymethyl-2-ethyl-3- (3-cyanopropyl) imidazolium, 1-ethoxy-2-methyl-3- (4-cyanobutyl) imidazolium,

1-ethoxymethyl-2-ethyl-3- (4-cyanobutyl) imidazolium, 1- (2-ethoxyethyl) -2-methyl-3-cyanomethylimidazolium, 1- (2-ethoxyethyl) -2- Ethyl-3-cyanomethylimidazolium, 1- (2-ethoxyethyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (2-ethoxyethyl) -2-ethyl-3- (2- Cyanoethyl) imidazolium, 1- (2-ethoxyethyl) -2-methyl-3- (3-cyanopropyl) imidazolium, 1- (2-ethoxyethyl) -2-ethyl-3- (3-cyanopropyl) Imidazolium, 1- (3-ethoxypropyl) -2-methyl-3-cyanomethylimidazolium, 1- (3-ethoxypropyl) -2-ethyl-3-cyano Tilimidazolium, 1- (3-ethoxypropyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (3-ethoxypropyl) -2-ethyl-3- (2-cyanoethyl) imidazolium, 1- (3-ethoxypropyl) -2-methyl-3- (3-cyanopropyl) imidazolium, 1- (3-ethoxypropyl) -2-ethyl-3- (3-cyanopropyl) imidazolium, 1- (4-ethoxybutyl) -2-methyl-3-cyanomethylimidazolium, 1- (4-ethoxybutyl) -2-ethyl-3-cyanomethylimidazolium,

1-propoxymethyl-2-methyl-3-cyanomethylimidazolium, 1-propoxymethyl-2-ethyl-3-cyanomethylimidazolium, 1-propoxymethyl-2-methyl-3- (2-cyanoethyl) imidazolium 1-propoxymethyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1-propoxymethyl-2-methyl-3- (3-cyanopropyl) imidazolium, 1-propoxymethyl-2-ethyl-3 -(3-cyanopropyl) imidazolium, 1- (2-propoxyethyl) -2-methyl-3-cyanomethylimidazolium, 1- (2-propoxyethyl) -2-ethyl-3-cyanomethylimidazolium, 1- (2-propoxyethyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- 2-propoxyethyl) -2-ethyl-3- (2-cyanoethyl) imidazolium, 1- (3-propoxypropyl) -2-methyl-3-cyanomethylimidazolium, 1- (3-propoxypropyl) -2 -Ethyl-3-cyanomethylimidazolium, 1-merthiomethyl-2-methyl-3- (2-methylthioethyl) imidazolium, 1-merthiomethyl-2-ethyl-3- (2-methylthioethyl) imidazolium, 1- Methylthiomethyl-2-methyl-3- (2-ethylthioethyl) imidazolium, 1-methylthiomethyl-2-ethyl-3- (2-ethylthioethyl) imidazolium, 1- (2-methylthioethyl) -2 -Methyl-3- (2-ethylthioethyl) imidazolium, 1- (2-methylthioethyl) -2-ethyl- - (2-ethylthioethyl) imidazolium, 1- (2-ethyl-thio) -2-methyl-3- (2-ethyl thioethyl) imidazolium,

1- (2-ethylthiomethyl) -2-ethyl-3- (2-ethylthioethyl) imidazolium, 1- (2-ethylthioethyl) -2-methyl-3- (3-methylthiopropyl) imidazolium 1- (2-ethylthioethyl) -2-ethyl-3- (3-methylthiopropyl) imidazolium, 1-methylthiomethyl-2-methyl-3-cyanomethylimidazolium, 1-methylthiomethyl-2-ethyl -3-cyanomethylimidazolium, 1-methylthiomethyl-2-methyl-3- (2-cyanoethyl) imidazolium, 1-methylthiomethyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1-methylthiomethyl 2-methyl-3- (3-cyanopropyl) imidazolium, 1-methylthiomethyl-2-ethyl-3- (3-sia Propyl) imidazolium, 1-methylthiomethyl-2-methyl-3- (4-cyanobutyl) imidazolium, 1-methylthiomethyl-2-ethyl-3- (4-cyanobutyl) imidazolium, 1- (2-methylthioethyl) ) -2-Methyl-3-cyanomethylimidazolium, 1- (2-methylthioethyl) -2-ethyl-3-cyanomethylimidazolium, 1- (2-methylthioethyl) -2-methyl-3- (2) -Cyanoethyl) imidazolium, 1- (2-methylthioethyl) -2-ethyl-3- (2-cyanoethyl) imidazolium, 1- (2-methylthioethyl) -2-methyl-3- (3-cyanopropyl) Imidazolium, 1- (2-methylthioethyl) -2-ethyl-3- (3-cyanopropyl) imidazolium, 1- (2- Chiruchioechiru) -2-methyl-3- (4-cyanobutyl) imidazolium, 1- (2-methylthioethyl) -2-ethyl-3- (4-cyanobutyl) imidazolium,

1- (3-methylthiopropyl) -2-methyl-3-cyanomethylimidazolium, 1- (3-methylthiopropyl) -2-ethyl-3-cyanomethylimidazolium, 1- (3-methylthiopropyl) -2 -Methyl-3- (2-cyanoethyl) imidazolium, 1- (3-methylthiopropyl) -2-ethyl-3- (2-cyanoethyl) imidazolium, 1- (4-methylthiobutyl) -2-methyl-3 -Cyanomethylimidazolium, 1- (4-methylthiobutyl) -2-ethyl-3-cyanomethylimidazolium, 1- (4-methylthiobutyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1 -(4-Methylthiobutyl) -2-ethyl-3- (2-cyanoethyl) imidazolium, 1-ethylthiomethyl-2-methyl- -Cyanomethylimidazolium, 1-ethylthiomethyl-2-ethyl-3-cyanomethylimidazolium, 1-ethylthiomethyl-2-methyl-3- (2-cyanoethyl) imidazolium, 1-ethylthiomethyl-2 -Ethyl-3- (2-cyanoethyl) imidazolium, 1-ethylthiomethyl-2-methyl-3- (3-cyanopropyl) imidazolium, 1-ethylthiomethyl-2-ethyl-3- (3-cyano Propyl) imidazolium, 1-ethylthiomethyl-2-methyl-3- (4-cyanobutyl) imidazolium, 1-ethylthiomethyl-2-ethyl-3- (4-cyanobutyl) imidazolium, 1- (2- Ethylthioethyl) -2-methyl-3-cyanomethylimidazolium, 1- (2-ethylthioethyl) -2-ethyl-3- Anomethylimidazolium, 1- (2-ethylthioethyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (2-ethylthioethyl) -2-ethyl-3- (2-cyanoethyl) Imidazolium, 1- (2-ethylthioethyl) -2-methyl-3- (3-cyanopropyl) imidazolium, 1- (2-ethylthioethyl) -2-ethyl-3- (3-cyanopropyl) Imidazolium, 1- (3-ethylthiopropyl) -2-methyl-3-cyanomethylimidazolium, 1- (3-ethylthiopropyl) -2-ethyl-3-cyanomethylimidazolium, 1- (3- Ethylthiopropyl) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (3-ethylthiopropyl) -2-ethyl-3- (2-cyanoethyl) imi Dazolium,

1- (4-ethylthiobutyl) -2-methyl-3-cyanomethylimidazolium, 1- (4-ethylthiobutyl) -2-ethyl-3-cyanomethylimidazolium, 1- (4-ethylthiobutyl) ) -2-methyl-3- (2-cyanoethyl) imidazolium, 1- (4-ethylthiobutyl) -2-ethyl-3- (2-cyanoethyl) imidazolium, 1-cyanomethyl-2-methyl-3- (2-cyanoethyl) imidazolium, 1-cyanomethyl-2-ethyl-3- (2-cyanoethyl) imidazolium, 1-cyanomethyl-2-methyl-3- (3-cyanopropyl) imidazolium, 1-cyanomethyl-2 -Ethyl-3- (3-cyanopropyl) imidazolium, 1-cyanomethyl-2-methyl-3- (4-cyanobutyl) imidazolium, -Cyanomethyl-2-ethyl-3- (4-cyanobutyl) imidazolium, 1- (2-cyanoethyl) -2-methyl-3- (3-cyanopropyl) imidazolium, 1- (2-cyanoethyl) -2- Ethyl-3- (3-cyanopropyl) imidazolium, 1- (2-cyanoethyl) -2-methyl-3- (4-cyanobutyl) imidazolium, 1- (2-cyanoethyl) -2-ethyl-3- ( N, N, C-3 substituted imidazolium having an asymmetric structure such as 4-cyanobutyl) imidazolium.

  3 or less (N-1 substitution type, N, N-2 substitution type, N, C-2 substitution type, N, N, C-3 substitution type) as described above and each substituted alkyl group has 10 or less carbon atoms Among these imidazoliums, N, N-2 substitution type and N, N, C-3 substitution type are more preferable from the viewpoint of lowering melting point, and N, N having an asymmetric structure from the viewpoint of lowering viscosity. -2 substitution type and N, N, C-3 substitution type having an asymmetric structure are preferable, and 1-ethyl-3-methylimidazolium and 1-butyl-3 are particularly preferable from the viewpoint of oxidation resistance and reduction resistance. -Methylimidazolium, 1-ethyl-3,4-dimethylimidazolium, 3-ethyl-1,2-dimethyl-imidazolium, 1,2-dimethyl-3-propylimidazolium, 1-butyl-2,3- Dimethylimidazolium is preferred. These imidazolium-based cations may be used in combination of two or more.

  Examples of the pyrrolidinium cation include N, N-dimethylpyrrolidinium, N-ethyl-N-methylpyrrolidinium, N-methyl-N-propylpyrrolidinium, N-butyl-N-methylpyrrolidi. Ni, N-methyl-N-pentylpyrrolidinium, N-hexyl-N-methylpyrrolidinium, N-methyl-N-octylpyrrolidinium, N-decyl-N-methylpyrrolidinium, N-dodecyl- N-methylpyrrolidinium, N- (2-methoxyethyl) -N-methylpyrrolidinium, N- (2-ethoxyethyl) -N-methylpyrrolidinium, N- (2-propoxyethyl) -N- Examples include methylpyrrolidinium, N- (2-isopropoxyethyl) -N-methylpyrrolidinium, and the like.

  Examples of piperidinium-based cations include N, N-dimethylpiperidinium, N-ethyl-N-methylpiperidinium ion, N-methyl-N-propylpiperidinium, N-butyl-N-methylpiperidinium, N-methyl-N-pentylpiperidinium, N-hexyl-N-methylpiperidinium, N-methyl-N-octylpiperidinium, N-decyl-N-methylpiperidinium, N-dodecyl-N- Methylpiperidinium, N- (2-methoxyethyl) -N-methylpiperidinium, N- (2-methoxyethyl) -N-ethylpiperidinium, N- (2-ethoxyethyl) -N-methylpi Peridinium, N-methyl-N- (2-methoxyphenyl) piperidinium, N-methyl-N- (4-methoxyphenyl) piperidinium Ethyl -N- N-(2-methoxyphenyl) piperidinium, N- ethyl -N- (4-methoxyphenyl) piperidinium and the like.

  Examples of the quaternary ammonium cation include N, N, N, N-tetramethylammonium, N, N, N-trimethylethylammonium, N, N, N-trimethylpropylammonium, N, N, N-trimethylbutyl. Ammonium, N, N, N-trimethylpentylammonium, N, N, N-trimethylhexylammonium, N, N, N-trimethylheptylammonium, N, N, N-trimethyloctylammonium, N, N, N-trimethyldecyl Ammonium, N, N, N-trimethyldodecylammonium, N-ethyl-N, N-dimethylpropylammonium, N-ethyl-N, N-dimethylbutylammonium, N-ethyl-N, N-dimethylhexylammonium, 2- Methoxy-N, N, N-trimethylethyl Ammonium, 2-ethoxy-N, N, N-trimethylethylammonium, 2-propoxy-N, N, N-trimethylethylammonium, N- (2-methoxyethyl) -N, N-dimethylpropylammonium, N- ( 2-methoxyethyl) -N, N-dimethylbutylammonium.

  Thus, the ionic liquid of the present invention is formed. In the present invention, the melting point is preferably room temperature or lower, more preferably 0 or lower, particularly preferably −30 or lower. If the melting point is too high, the conductivity at low temperatures tends to be unable to be maintained. In addition, as a lower limit of melting | fusing point, it is -200 degreeC normally. In general, it is known that when an electrolyte salt such as a lithium salt is blended with an ionic liquid, the melting point drops. However, the melting point in the present invention is a numerical value when no electrolyte salt is blended.

The viscosity (25 ° C.) of the ionic liquid of the present invention is preferably 1 Pa · s or less, more preferably 0.5 Pa · s or less, still more preferably 0.3 Pa · s or less, and particularly preferably 0.2 Pa · s. s or less. If the viscosity is too high, the conductivity tends to decrease. The lower limit of the viscosity is usually 0.001 Pa · s.

The boiling point of the ionic liquid of the present invention is preferably 200 ° C. or higher, more preferably 250 ° C. or higher, and particularly preferably 300 ° C. or higher.
The thermal decomposition temperature of the ionic liquid is preferably 200 ° C. or higher, more preferably 250 ° C. or higher, and particularly preferably 300 ° C. or higher from the viewpoint of flame retardancy. The upper limit of the decomposition temperature is usually 500 ° C. Here, the decomposition temperature is a temperature at which weight loss reaches 5% in a temperature rise measurement by TG (Thermogravimetry).

  Next, the manufacturing method of the ionic liquid of this invention which has (beta) -carbonylenolate type | system | group anion is demonstrated. Here, the case where an imidazolium-based cation is used as a cation will be described. However, a cation other than an imidazolium-based cation can be similarly produced.

The ionic liquid of the present invention can be obtained by reacting a halide of an imidazolium cation with a β-carbonyl enolate type compound in the presence of a basic compound. This reaction is preferably carried out in the presence of a halogen ion scavenger.
Hereinafter, as a preferred embodiment of the present invention, a method for producing an ionic liquid having a β-diketone type enolate anion using a halide of alkylimidazolium and a β-diketone type compound will be described.

  The alkyl imidazolium halide used as a cation source can be obtained by reacting imidazole with an alkyl halide and quaternizing ammonium chloride. As the halogen, chlorine, bromine and iodine are preferable. On the other hand, a β-diketone type compound is used as the anion source. A target ionic liquid is obtained by stirring a halide serving as a cation source and a β-diketone type compound serving as an anion source in the presence of a basic compound in a reaction solvent and reacting at room temperature to 200 ° C. for several minutes. Can do.

  Examples of the basic compound include hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, magnesium hydroxide, and calcium hydroxide. Among these, potassium hydroxide is particularly preferable from the viewpoint of solubility.

  Examples of the reaction solvent include polar solvents such as water, alcohol, acetone, and acetonitrile, and nonpolar solvents such as hexane and heptane. A solvent that can be easily treated is selected in consideration of the properties of the ionic liquid to be generated. It is preferable. For example, when the ionic liquid to be generated is hydrophobic, water is used as a solvent, and the resulting reaction solution is washed with water to remove the metal halide salt generated, and the water is removed by vacuum drying to remove ions. It is preferred to produce a liquid. Conversely, if the ionic liquid produced is water-soluble, use a solvent that does not dissolve the metal halide salt produced in the reaction in advance, remove the precipitated metal halide salt by filtration, and then remove the solvent by vacuum drying. It is preferable to manufacture an ionic liquid by doing.

  In this reaction, it is preferable to use a halogen ion scavenger. Examples of the halogen ion scavenger include silver nitrate and ion exchange resin. Among these, silver nitrate is preferable because halogen ions can be easily collected. The amount of the collecting agent used is preferably 50 to 30000% by weight with respect to the halogen ions. More preferably, it is 100-20000 weight%, More preferably, it is 150-15000 weight%, Most preferably, it is 200-10000 weight%. If the amount used is too large, purification after the reaction tends to be difficult, and conversely if it is small, the reaction tends to hardly proceed.

  The ionic liquid produced by the above reaction is preferably purified by column chromatography. By purifying, impurities in the ionic liquid can be removed, and when used as an electrolyte material, electrochemical characteristics such as conductivity and potential window can be improved. Examples of the column include alumina, silica gel, diatomaceous earth, activated carbon, and the like, and alumina is particularly preferable because impurity ions can be efficiently removed.

  The electrical conductivity of the ionic liquid thus obtained is preferably 0.0001 mS / cm or more at −30 ° C., more preferably 0.001 mS / cm or more, and further preferably 0.002 mS / cm or more. If the conductivity at −30 ° C. is too low, it tends to be difficult to use as an electrolyte.

  The ionic liquid (A) of the present invention is useful as an electrolyte material. By containing the ionic liquid (A) and the electrolyte salt (B), the ionic liquid (A) is an electrolyte suitable as a lithium secondary battery.

As the electrolyte salt used in the present invention (B), for example, LiBF _4, LiBR ₄ (R is a phenyl group or an alkyl _{group), LiPF 6, LiSbF 6,} LiAsF 6, LiCIO 4, LiSO 3 CF 3, LiN (SO _{2 CF 3) 2, LiN (} SO 2 F) 2, LiN (CN) 2, LiC (SO 2 CF 3) 3, LiSO 3 C 6 F 13, LiSO 3 C 8 F 17, LiAlCl 4, lithium tetrakis [3 , 5-bis (trifluoromethyl) phenyl] borate or the like. Among these, LiN (SO ₂ CF ₃ ) ₂ , LiBF ₄ , and LiPF ₆ are preferably used from the viewpoint of solubility in an ionic liquid.

  The content ratio of the ionic liquid (A) to the electrolyte salt (B) is preferably ionic liquid (A) / electrolyte salt (B) = 95/5 to 50/50 (weight ratio), more preferably 90 / It is 10-60 / 40 (weight ratio), Most preferably, it is 85 / 15-70 / 30 (weight ratio). If the content is out of the above range, poor conductivity tends to occur.

  The conductivity of the electrolyte thus obtained is preferably 0.001 mS / cm or more at −30 ° C., more preferably 0.005 mS / cm or more, and still more preferably 0.01 mS / cm or more. If the electrical conductivity at −30 ° C. is too small, it tends to be difficult to use the lithium secondary battery for automobiles. The upper limit of conductivity is usually 100 mS / cm.

  In the present invention, in addition to the ionic liquid (A) and the electrolyte salt (B), an ionic liquid (A ′) other than the ionic liquid (A) can be further contained.

The ionic liquid (A ′) other than the ionic liquid (A) is not particularly limited. For example, as anions, chlorine anions, bromine anions, iodine anions, BF ₄ ⁻ , BF ₃ CF ₃ ⁻ , BF ₃ C ₂ F ₅ ⁻ , BF ₃ C ₃ F ₇ ⁻ , BF ₃ C ₄ F ₉ ⁻ , PF ₆ ⁻ , NO ₃ ⁻ , CF ₃ CO ₂ ⁻ , CF ₃ SO ₃ ⁻ , (CF ₃ SO ₂ ) ₂ N ⁻ , (FSO ₂ ) ₂ N ⁻ , (CN) ₂ N ⁻ , (CF ₃ SO ₂ ) ₃ C ⁻ , (C ₂ F ₅ SO ₂ ) ₂ N ⁻ , AlCl ₄ ⁻ , Al ₂ Cl ₇ ^{− and the} like The corresponding cations include 1,3-dimethylimidazolium, 1-ethyl-3-methylimidazolium, 1-butyl-3-methylimidazolium, 1-hexyl-3-methylimidazolium, 1-octyl- 3-methylimidazolium, 1-butyl-2,3-dimethylimid Other than imidazolium cations, such as zolium, alkylimidazolium cations such as 1,2,3-trimethylimidazolium, 1,2-dimethyl-3-ethylimidazolium, etc., quaternary ammonium cations, pyridinium cations, quaternary phosphonium cations, etc. An ionic liquid containing These ionic liquids (A ′) can be used alone or in combination.

  The mixing ratio of the ionic liquid (A) and the other ionic liquid (A ′) is not particularly limited, but when the total ionic liquid is 100 parts by weight, the ionic liquid (A ′) is preferably 50 parts by weight or less, More preferably, it is 30 parts by weight or less, and particularly preferably 20 parts by weight or less. When there is too much ionic liquid (A '), it exists in the tendency for electrical conductivity and a charge / discharge characteristic to fall.

  Furthermore, in this invention, it is preferable to use an electrode protective film forming agent (C) in order to improve charge / discharge characteristics when a battery is prepared using this electrolyte. Examples of the electrode protective film forming agent (C) include vinylene carbonate, 1,3-propane sultone, ethylene sulfite, triethyl borate, butyl methyl sulfonate, and the like. Among these, vinylene carbonate is particularly preferable from the viewpoint of forming stable SEI (Solid Electrolyte Interface).

  As content of this electrode protective film formation agent (C), it is preferable that it is 0.1-5 weight part with respect to 100 weight part of ionic liquid (A), More preferably, 0.2-3 weight part, Particularly preferred is 0.3 to 1 part by weight. If the content is too large, the charge / discharge characteristics of the battery tend to decrease, and if the content is too small, the charge / discharge capacity retention rate of the lithium secondary battery tends to decrease.

  Moreover, in order to improve the charge / discharge characteristics of the battery or improve safety, the electrolyte of the present invention preferably further contains inorganic fine particles (D) to form a gel solid electrolyte. .

  Such inorganic fine particles (D) are preferably chemically stable inorganic oxides, and examples of such inorganic oxides include IIA to VA groups such as magnesium, silicon, aluminum, zirconium and titanium, transition metals, IIIB and IVB. Oxides can be mentioned. Among these, oxides of titanium, silicon, and aluminum are more preferable, silicon oxide (silica) is more preferable, and hydrophilic silica is particularly preferable.

  The hydrophilic silica generally has a hydroxyl group on the surface of silicon oxide. Specific examples thereof include “Aerosil 300”, “Aerosil 200”, “Aerosil 100”, “Aerosil 50” manufactured by Nippon Aerosil Co., Ltd. Or the like.

  The particle size of the inorganic fine particles (D) is preferably 1000 nm or less from the viewpoint of improving charge / discharge characteristics. A more preferable particle diameter is 1 to 100 nm, and particularly preferably 2 to 50 nm. If the particle size is too large, the charge / discharge capacity retention rate of the lithium secondary battery tends to decrease.

  The content of the inorganic fine particles (D) is preferably 1 to 30 parts by weight, more preferably 2 to 20 parts by weight with respect to 100 parts by weight of the ionic liquid (A). When the content is too small, the charge / discharge characteristics tend to decrease, and when the content is too large, the conductivity tends to decrease.

  In the present invention, it is also possible to add a small amount of an organic solvent to improve the electrical conductivity. Examples of the organic solvent include carbonate solvents (propylene carbonate, ethylene carbonate, butylene carbonate, dimethyl carbonate, diethyl carbonate, etc.), amide solvents (N-methylformamide, N-ethylformamide, N, N-dimethylformamide, N-methylacetamide, N-ethylacetamide, N-methylpyrrolidinone, etc.), lactone solvents (γ-butyllactone, γ-valerolactone, δ-valerolactone, 3-methyl-1,3-oxazolidine-2- ON), alcohol solvents (ethylene glycol, propylene glycol, glycerin, methyl cellosolve, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, diglycerin, polyoxyalkylene glycol Chlorohexanediol, xylene glycol, etc.), ether solvent (methylal, 1,2-dimethoxyethane, 1,2-diethoxyethane, 1-ethoxy-2-methoxyethane, alkoxypolyalkylene ether, etc.), nitrile solvent (benzonitrile) , Acetonitrile, 3-methoxypropionitrile, etc.), phosphoric acids and phosphoric acid ester solvents (eg orthophosphoric acid, metaphosphoric acid, pyrophosphoric acid, polyphosphoric acid, phosphorous acid, trimethyl phosphate), 2-imidazolidinones (1,3- Dimethyl-2-imidazolidinone), pyrrolidones, sulfolane solvents (sulfolane, tetramethylene sulfolane, etc.), furan solvents (tetrahydrofuran, 2-methyltetrahydrofuran, 2,5-dimethoxytetrahydrofuran, etc.), dioxolane, dioxane, etc. ,this Alone or a mixed solvent can be used. Among these, carbonate-based solvents, ether-based solvents, and furan-based solvents are preferable from the viewpoint of conductivity, and carbonate-based solvents are particularly preferably used from the viewpoint of charge / discharge characteristics of the battery.

  The content in the case of using an organic solvent is preferably 30% by volume or less, particularly preferably 5 to 20% by volume when the entire electrolyte is 100% by volume. If the content is too large, the flame retardancy tends to decrease.

The electrolyte of the present invention comprises the above ionic liquid (A) and electrolyte salt (B), if necessary, other ionic liquid (A ′), electrode protective film forming agent (C), inorganic fine particles (D), It is produced by mixing organic solvents so as to form a homogeneous solution. Mixing is performed in a dry room or a dry box.
Thus, an electrolyte containing the ionic liquid (A) and the electrolyte salt (B) of the present invention is obtained.

Next, a lithium secondary battery obtained using the electrolyte of the present invention will be described.
In the present invention, a lithium secondary battery is produced by sandwiching the electrolyte of the present invention obtained above between a positive electrode and a negative electrode.

  Such a positive electrode is preferably a composite positive electrode. A composite positive electrode refers to a composition in which a positive electrode active material is mixed with a conductive additive such as ketjen black or acetylene black, a binder such as polyvinylidene fluoride, and an ion conductive polymer as required. It is applied to a conductive metal plate.

  As the positive electrode active material, for example, an inorganic active material, an organic active material, and a composite thereof can be exemplified. Is preferable from the viewpoint of increasing.

As inorganic-based active material, Li _0.3 MnO ₂ in a _{3V, Li 4 Mn 5 O 12,} V 2 O 5 , _{etc., LiCoO 2, LiMn 2 O 4} , LiNiO metal oxide such as ₂ is 4V-based, TiS _2, MoS ₂ and metal sulfides such as FeS, and complex oxides of these compounds and lithium. Examples of the organic active material include conductive polymers such as polyacetylene, polyaniline, polypyrrole, polythiophene, and polyparaphenylene, organic disulfide compounds, carbon disulfide, and active sulfur.

  With regard to the negative electrode, for example, a metal-based negative electrode in which a negative electrode active material is directly applied to a current collector, an active material such as a conductive polymer, a carbon body, and an oxide with a binder such as polyvinylidene fluoride on an alloy-based current collector. Examples include a negative electrode coated with a substance.

Examples of the negative electrode active material include lithium metal and silicon metal, alloys of metals such as lithium, silicon, aluminum, lead, tin, silicon, and magnesium, metal oxides such as SnO ₂ and TiO ₂ , polypyridine, polyacetylene, polythiophene, or Examples include cation-doped conductive polymers composed of these derivatives, carbon bodies capable of occluding lithium, and the like. Particularly, when the ionic liquid (A) of the present invention is used, lithium metal having a high energy density or Silicon metal is preferred.

  In the present invention, when such lithium metal is used, the thickness of the lithium metal is usually preferably 5 to 500 μm. It is economical and preferable to use lithium foil as the lithium metal.

  The lithium secondary battery of the present invention is produced by sandwiching an electrolyte between the positive electrode and the negative electrode, but a separator is preferably used from the viewpoint of preventing a short circuit. Specifically, a lithium secondary battery is obtained by impregnating a separator with an electrolyte and sandwiching the separator between a positive electrode and a negative electrode.

  As the separator, those having low resistance to ion migration of lithium ions are used, and for example, selected from polypropylene, polyethylene, polyester, polytetrafluoroethylene, polyvinyl alcohol, and saponified ethylene-vinyl acetate copolymer. Examples thereof include a microporous film made of one or more materials, an organic or inorganic nonwoven fabric, or a woven fabric. In these, the microporous film and glass nonwoven fabric which consist of polypropylene or polyethylene are preferable at the point of short circuit prevention and economical efficiency.

  Although it does not specifically limit as a form of the lithium secondary battery of this invention, The battery cell of various forms, such as a coin, a sheet | seat, a cylinder, is mentioned.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further more concretely, this invention is not limited to a following example, unless the summary is exceeded.
In the examples, “parts” and “%” mean weight basis unless otherwise specified.
The measurement conditions for each characteristic are as follows.

(viscosity)
Using “AR-1000 type rotational rheometer” manufactured by TA Instruments, the measurement geometry (diameter 40 mm, 2 ° cone plate) was measured at 25 ° C. and applied stress 20 Pa.

(Melting point)
Using a “D2920 type DSC” manufactured by TA Instruments, the sample was sealed in a liquid-dedicated pan, and the temperature was increased from −150 ° C. to 100 ° C. at 10 ° C./minute in a nitrogen atmosphere.

(boiling point)
The temperature was increased from 25 ° C. to 300 ° C. at a rate of 10 ° C./min.

(conductivity)
After being immersed in an electrolyte for 5 hours using “CG-511B type cell” manufactured by Toa DKK as a measurement cell, measurement was performed by an alternating current impedance method using an electrochemical measurement system “Solartron 1280Z” (manufactured by Solartron, UK). . The AC amplitude was measured at 5 mV, and the frequency range was 20 k to 0.1 Hz.

(Charge / discharge characteristics)
And a charge-discharge measuring instrument was used made instrument center, charged to 4.2V at a current density of 0.2 mA / cm ^2, and after 10 minutes of rest, to 3V at a current density of 0.2 mA / cm ² discharge This charge / discharge was repeated at 25 ° C., and the charge / discharge capacity retention rate (%) at the 100th cycle was measured. The evaluation criteria are as follows.
◎ ・ ・ ・ Capacity maintenance ratio is 95% or more ○ ・ ・ ・ Capacity maintenance ratio is 90% or more and less than 95% × ・ ・ ・ Capacity maintenance ratio is less than 90%

Example 1
[Synthesis of Ionic Liquid (A-1)]
Into a 500 mL Erlenmeyer flask was added 8.6 g of potassium hydroxide, 200 mL of methanol was added to dissolve, and 20.0 g of trifluoroacetylacetone (1,1,1-trifluoro-2,4-pentanedionate) was further added. . To the solution, 24.8 g of 1-methyl-3-ethylimidazolium bromide was added and stirred for 10 minutes. 130 mL of 1M silver nitrate aqueous solution was added to precipitate AgBr, followed by filtration, and the filtrate was concentrated. Chloroform was added to the concentrated liquid for extraction, followed by concentration again to obtain 29.8 g of ionic liquid (A-1).

The ¹ H-NMR chart of the ionic liquid (A-1) is as shown in FIG. 1 and was confirmed to be the target 1-methyl-3-ethylimidazolium trifluoroacetylacetonate. NMR was measured using “Unity-300” manufactured by Varian, using deuterated chloroform as a solvent.
Moreover, main things about chart attribution are shown below.
10.58 ppm [s, 1H, NC (H) N]
7.29 ppm [s, 1H, NC (H) CH]
7.28 ppm [s, 1 H, NCHC (H)]
5.35 ppm [s, 1H, COC (H) CO]
4.31 ppm [q, 2H, NCH ₂ ]
4.00 ppm [s, 3H, NCH ₃ ]
2.67 ppm [br, 1H, OH]
2.10 ppm [s, 2H, COCH ₃ ]
1.55 ppm [t, 3H, CH ₂ CH ₃ ]

The obtained ionic liquid (A-1) has a viscosity at 25 ° C. of 0.10 Pa · s and is a low-viscosity liquid near room temperature. No melting point is observed between −150 to 300 ° C., and it can be used as an electrolyte even at a low temperature. Further, even when heated to 400 ° C., the boiling point was not observed, and it was confirmed that it was excellent in safety.
The conductivity of the obtained ionic liquid (A-1) at 25 ° C. and −30 ° C. is 2.8 mS / cm and 0.002 mS / cm, respectively, and has high conductivity, particularly at low temperatures. It was confirmed to be excellent.

(Preparation of electrolyte)
Furthermore, ₂ g of LiN (SO ₂ CF ₃ ) ₂ as an electrolyte salt (B) was mixed and dissolved in 8.0 g of the ionic liquid (A-1) to obtain an electrolyte [I].
The obtained electrolyte [I] has electrical conductivities at 25 ° C. and −30 ° C. of 2.6 mS / cm and 0.009 mS / cm, respectively, and has high electrical conductivity, particularly excellent conductivity at low temperatures. Was confirmed.

[Production of lithium secondary battery]
(1) Preparation of positive electrode 9.0 g of LiCoO ₂ powder, 0.5 g of ketjen black, and 0.5 g of polyvinylidene fluoride were mixed, and 7.0 g of 1-methyl-2-pyrrolidone was further added and mixed well in a mortar. A positive electrode slurry was obtained. The obtained positive electrode slurry was applied on an aluminum foil having a thickness of 20 μm using a wire bar in the air, dried at 100 ° C. for 15 minutes, and further dried at 80 ° C. for 1 hour under reduced pressure to obtain a film thickness of 30 μm. A composite positive electrode was prepared.

(2) Battery assembly After the electrolyte [I] is impregnated into a separator (ADVANTEC glass nonwoven fabric “GA-100”, thickness 440 μm) and a composite positive electrode, a separator and a lithium foil as a negative electrode are formed on the composite positive electrode. The layers were stacked in the order of (thickness 500 μm), inserted into a 2032 type coin cell, and sealed to obtain a lithium secondary battery.

  As a result of measuring the charge / discharge characteristics of the obtained lithium secondary battery, this battery has a good charge / discharge capacity retention rate, and the electrolyte made of the ionic liquid (A-1) is electrochemically stable. It was confirmed that there was.

Example 2
[Synthesis of ionic liquid (A-2)]
Into a 500 mL Erlenmeyer flask was added 6.3 g of potassium hydroxide, 200 mL of methanol was added to dissolve, and further 20.2 g of hexafluoroacetylacetone (1,1,1-trifluoro-2,4-pentanedionate) was added. . To the solution, 28.4 g of 1-methyl-3-butylimidazolium bromide was added and stirred for 10 minutes. 130 mL of 1M aqueous silver nitrate solution was added to precipitate AgBr, followed by filtration and concentration of the filtrate. Chloroform was added to the concentrated liquid for extraction, followed by concentration again to obtain 34.0 g of an ionic liquid (A-2).

The ¹ H-NMR chart of the ionic liquid (A-2) is as shown in FIG. 2 and was confirmed to be the target 1-methyl-3-butylimidazolium trifluoroacetylacetonate.
The main chart attributions are shown below.
10.54 ppm [s, 1H, NC (H) N]
7.27 ppm [s, 1H, NC (H) CH]
7.24 ppm [s, 1 H, NCHC (H)]
5.35 ppm [s, 1H, COC (H) CO]
4.21 ppm [q, 2H, NCH ₂ ]
4.00 ppm [s, 3H, NCH ₃ ]
2.67 ppm [br, 1H, OH]
2.10 ppm [s, 2H, COCH ₃ ]
1.84 ppm [quintet, 2H, NCH ₂ CH ₂ ]
1.36 ppm [sextet, 2H, CH ₂ CH ₃ ]
0.95 ppm [t, 3H, CH ₂ CH ₃ ]

The obtained ionic liquid (A-2) has a viscosity at 25 ° C. of 0.18 Pa · s, and is a low-viscosity liquid near room temperature. The melting point is not observed, and it can be used as an electrolyte even at a low temperature. Further, even when heated to 400 ° C., the boiling point was not observed, and it was confirmed that it was excellent in safety.
The conductivity of the obtained ionic liquid (A-2) at 25 ° C. and −30 ° C. is 1.2 mS / cm and 0.001 mS / cm, respectively, and has high conductivity, particularly at low temperature. It was confirmed to be excellent.

(Preparation of electrolyte)
An electrolyte [II] was obtained in the same manner as in Example 1 except that the ionic liquid (A-2) was used instead of the ionic liquid (A-1).
The conductivity of the obtained electrolyte [II] is as shown in Table 2. It was confirmed that the electrolyte [II] has a high conductivity and particularly excellent conductivity at a low temperature.

[Production of lithium secondary battery]
A lithium secondary battery was produced in the same manner as in Example 1 using the obtained electrolyte [II].

  The charge / discharge characteristics of the obtained lithium secondary battery are as shown in Table 2. This battery has a good charge / discharge capacity retention rate, and the electrolyte made of the ionic liquid (A-2) is electrically charged. It was confirmed to be chemically stable.

Example 3
[Synthesis of ionic liquid (A-3)]
Add 6.3 g of potassium hydroxide to a 500 mL Erlenmeyer flask, dissolve in 200 mL of methanol, and further add hexafluoroacetylacetone (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate). 20.0 g was added. To the solution, 21.2 g of 1-methyl-3-butylimidazolium bromide was added and stirred for 10 minutes. After adding 96 mL of 1M aqueous silver nitrate solution to precipitate AgBr, the filtrate was concentrated by filtration. Chloroform was added to the concentrated liquid for extraction, followed by concentration again to obtain 26.8 g of ionic liquid (A-3).

The ¹ H-NMR chart of the ionic liquid (A-3) is as shown in FIG. 3, and it was confirmed that it was the target 1-methyl-3-butylimidazolium hexafluoroacetylacetonate.
The main chart attributions are shown below.
10.38 ppm [s, 1H, NC (H) N]
7.15 ppm [s, 2H, NC ₂ H ₂ ]
5.72 ppm [s, 1H, COC (H) CO]
4.21 ppm [q, 2H, NCH ₂ ]
3.99 ppm [s, 3H, NCH ₃ ]
1.82 ppm [quintet, 2H, NCH ₂ CH ₂ ]
1.35 ppm [sextet, 2H, CH ₂ CH ₃ ]
0.94 ppm [t, 3H, CH ₂ CH ₃ ]

The obtained ionic liquid (A-3) has a viscosity at 25 ° C. of 0.06 Pa · s, and is a low-viscosity liquid near room temperature. The melting point is not observed, and it can be used as an electrolyte even at a low temperature. Further, even when heated to 400 ° C., the boiling point was not observed, and it was confirmed that it was excellent in safety.
The conductivity of the obtained ionic liquid (A-3) at 25 ° C. and −30 ° C. is 2.2 mS / cm and 0.006 mS / cm, respectively, and has high conductivity, particularly at low temperature. It was confirmed to be excellent.

(Preparation of electrolyte)
An electrolyte [III] was obtained in the same manner as in Example 1 except that the ionic liquid (A-3) was used instead of the ionic liquid (A-1).
The conductivity of the obtained electrolyte [III] is as shown in Table 2. It was confirmed that the electrolyte [III] has a high conductivity and particularly excellent conductivity at a low temperature.

[Production of lithium secondary battery]
A lithium secondary battery was produced in the same manner as in Example 1 using the obtained electrolyte [III].

  The charge / discharge characteristics of the obtained lithium secondary battery are as shown in Table 2. This battery has a good charge / discharge capacity retention rate, and the electrolyte made of the ionic liquid (A-3) is electrically charged. It was confirmed to be chemically stable.

Example 4
(Preparation of electrolyte)
Electrolyte [IV] was obtained in the same manner as in Example 1 except that 0.1 g of vinylene carbonate (manufactured by Kishida Chemical Co., Ltd.) was added as an electrode protective film forming agent (C) to the electrolyte [I].
The conductivity of the obtained electrolyte [IV] is as shown in Table 2. It was confirmed that the electrolyte [IV] has a high conductivity and particularly excellent conductivity at a low temperature.

[Production of lithium secondary battery]
A lithium secondary battery was produced in the same manner as in Example 1 using the obtained electrolyte [IV].

  The charge / discharge characteristics of the obtained lithium secondary battery were as shown in Table 2, and this battery had a good charge / discharge capacity retention rate.

Example 5
(Preparation of electrolyte)
The electrolyte [V] was added to the electrolyte [IV] in the same manner as in Example 1 except that 2.0 g of hydrophilic silica (“Aerosil 300CF” manufactured by Nippon Aerosil Co., Ltd., particle size 7 nm) was added as inorganic fine particles (D). Obtained.
The conductivity of the obtained electrolyte [V] is as shown in Table 2. It was confirmed that the electrolyte [V] has a high conductivity and particularly excellent conductivity at a low temperature.

[Production of lithium secondary battery]
A lithium secondary battery was produced in the same manner as in Example 1 by using the obtained electrolyte [V].

  The charge / discharge characteristics of the obtained lithium secondary battery were as shown in Table 2, and this battery had a good charge / discharge capacity retention rate.

Comparative Example 1
Various characteristics were measured in the same manner as in Example 1 except that the ionic liquid (A-1) was changed to 1-methyl-3-ethylimidazolium · BF ₄ (A′-1). The viscosity, melting point, and boiling point at 25 ° C. are as shown in Table 1. Although the conductivity at 25 ° C. is excellent, the conductivity cannot be measured because it freezes at −30 ° C.
In addition, since the electrical conductivity in -30 degreeC cannot measure ionic liquid (A'-1), it did not perform until evaluation of subsequent electrolyte and evaluation of a lithium secondary battery.

Comparative Example 2
Various characteristics were measured in the same manner as in Example 1 except that the ionic liquid (A-1) was changed to ethylene carbonate / dimethyl carbonate (mixing ratio 1/1) used as the organic solvent electrolyte. Table 1 shows the viscosity, melting point, and boiling point at 25 ° C. The boiling point was 95 ° C., which was confirmed to be dangerous when used as a battery.
In addition, since the organic solvent electrolyte had a low boiling point and was dangerous, the subsequent conductivity evaluation, electrolyte evaluation, and lithium secondary battery evaluation were not performed.

注）表中の（ ）の数字は配合量（部）である。

Note) Numbers in parentheses in the table are blending amounts (parts).

  As is clear from the above evaluation results, the ionic liquid of Comparative Example 1 is frozen at a low temperature and thus does not measure conductivity, whereas the organic solvent electrolyte of Comparative Example 2 is dangerous because it has a low boiling point. The ionic liquids of the examples have a low melting point, excellent electrical conductivity at low temperatures, are safe, have excellent electrochemical stability, and are extremely effective as electrolytes for lithium secondary batteries. I understand.

  The ionic liquid of the present invention is useful as an electrolyte material, and the electrolyte using such an ionic liquid is an electrolyte containing an ionic liquid (A) having a β-carbonylenolate anion and an electrolyte salt (B). The electrolyte is excellent in performance as an electrolyte such as conductivity, particularly in low temperature operation and safety, and is very useful as an electrolyte for a lithium secondary battery.

2 is a ¹ H-NMR chart of the ionic liquid (A-1) obtained in Example 1. FIG. 2 is a ¹ H-NMR chart of an ionic liquid (A-2) obtained in Example 2. FIG. 2 is a ¹ H-NMR chart of an ionic liquid (A-3) obtained in Example 3. FIG.

Claims (16)

An ionic liquid having a β-carbonyl enolate anion represented by the following general formula (1) or (2):

(Here, R ₁ and R ₂ may be the same or different, and an alkyl group having 1 to 10 carbon atoms which may contain a halogen or an ether bond, or a C 1-10 carbon atom which may contain a halogen or an ether bond. R ₃ is a phenyl group, an alkyl group having 1 to 10 carbon atoms which may contain a halogen or an ether bond, or an alkoxy group having 1 to 10 carbon atoms which may contain a halogen or an ether bond.

(Wherein R ₁₂ is an alkylene group having 1 to 10 carbon atoms which may contain a halogen or an ether bond. R ₄ is a phenyl group, an alkyl group having 1 to 10 carbon atoms which may contain a halogen or an ether bond, Or it is a C1-C10 alkoxy group which may contain a halogen or an ether bond.) The ionic liquid according to claim 1, wherein the β-carbonyl enolate anion is a β-diketone enolate anion. The ionic liquid according to claim 1 or 2, wherein the β-carbonyl enolate anion has an asymmetric chemical structure. The ionic liquid according to claim 1, wherein the β-carbonyl enolate anion has a fluorinated alkyl group or a fluorinated alkylene group. The ionic liquid according to any one of claims 1 to 4, which has an imidazolium cation. 6. The ionic liquid according to claim 1, wherein the imidazolium cation is an imidazolium cation having an asymmetric chemical structure. Melting | fusing point is 0 degrees C or less, The ionic liquid in any one of Claims 1-6 characterized by the above-mentioned. The ionic liquid according to any one of claims 1 to 7, wherein a viscosity at 25 ° C is 1 Pa · s or less. The method for producing an ionic liquid according to any one of claims 5 to 8, wherein a halide of an imidazolium cation is reacted with a β-carbonylenolate type compound in the presence of a basic compound. Furthermore, it reacts in presence of a halogen ion scavenger, The manufacturing method of the ionic liquid of Claim 9 characterized by the above-mentioned. The method for producing an ionic liquid according to claim 9, wherein the ionic liquid is purified by column chromatography. An electrolyte comprising the ionic liquid (A) according to any one of claims 1 to 8 and an electrolyte salt (B). The electrolyte according to claim 12, further comprising an electrode protective film forming agent (C). The electrolyte according to claim 12 or 13, further comprising inorganic fine particles (D). The electrolyte according to any one of claims 12 to 14, which is used for a lithium secondary battery. A lithium secondary battery comprising the electrolyte according to claim 15 sandwiched between a positive electrode and a negative electrode.

Images