Compositions of New Borate Compounds

Abstract

An object of the present invention is to provide a composition of a borate compound soluble in a hydrocarbon solvent, which is useful as a cocatalyst for solution polymerization of hydrocarbons and dienes. According to the present invention, it is possible to provide a composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4) [the definitions of the respective symbols in the formula are as described in the specification], which is useful as a cocatalyst for polymerization of olefins and dienes, and a method for producing the same.

Description

Technical Field

[0001] The present invention relates to a composition containing a borate compound useful as a cocatalyst for a solution polymerization system of olefins and dienes, and a method for producing the same. Background Art

[0002] Conventionally, as catalysts for the polymerization of olefins and dienes, non-metallocene metal complex catalysts such as metallocene compounds, diimine complexes, and phenoxy complexes have often been reported. In most of the catalytic systems using these metal complex catalysts, methylaluminoxane and tetrakis(pentafluorophenyl)borate compounds are used as cocatalysts for stabilizing active species. Since the tetrakis(pentafluorophenyl)borate compound has excellent thermal stability compared to methylaluminoxane and a smaller stoichiometric ratio used relative to the metal complex than methylaluminoxane, it is widely used as a cocatalyst in solution polymerization systems.

[0003] In addition, as a solvent used in the polymerization of olefins and dienes using a metal complex catalyst, a non-polar hydrocarbon solvent is usually used. In particular, from the viewpoints of odor and toxicity, a switch is being made to aliphatic hydrocarbon solvents such as hexane rather than aromatic hydrocarbon solvents such as toluene.

[0004] However, it is known that a typical tetrakis(pentafluorophenyl)borate compound is hardly soluble in aromatic hydrocarbon solvents such as toluene, and even when dissolved, it separates into a concentrated phase in which the borate compound is dissolved and a dilute phase that is not dissolved, a liquid-liquid two-phase (Patent Document 1).

[0005] In addition, since a typical tetrakis(pentafluorophenyl)borate compound is hardly soluble in aliphatic hydrocarbon solvents such as hexane and heptane, a tetrakis(pentafluorophenyl)borate compound that is soluble in aliphatic hydrocarbon solvents has been desired and proposed (Patent Document 2). Di(octadecyl)methylammonium tetrakis(pentafluorophenyl)borate and bis(hydrogenated tallow alkyl)methylammonium tetrakis(pentafluorophenyl)borate described in Patent Document 2 are useful as compounds that are easily soluble in hydrocarbon solvents.

[0006] However, in the production method described in Patent Document 2, it is prepared by reacting lithium tetrakis(pentafluorophenyl)borate with a separately prepared hydrochloride of a dialkylmethylamine. In this method, there is a concern that lithium tetrakis(pentafluorophenyl)borate, a raw material that is hardly soluble in water, or the hydrochloride of a long-chain aliphatic amine remains in the product, and they become catalyst poisons and do not exhibit sufficient activity when used as a cocatalyst for polymerization. In fact, in Example 2 of Patent Document 2, diethyl ether remains in the product, so it is presumed that an ether complex of lithium tetrakis(pentafluorophenyl)borate that is hardly soluble in water remains.

[0007] In Patent Document 3, a method for producing an ammonium tetrakis(pentafluorophenyl)borate derivative is disclosed, in which an alkali metal salt of tetrakis(pentafluorophenyl)borate and an amine are mixed and then treated with a protonic acid. However, in this method, there is also a concern that an ether complex of the alkali metal salt of tetrakis(pentafluorophenyl)borate or a protonate of a long-chain aliphatic amine remains in the product and acts as a catalyst poison.

[0008] Patent Document 4 discloses a composition containing a trialkylammonium tetrakis(pentafluorophenyl)borate compound and an amine compound, and a method for producing the same, and discloses that the composition is soluble in a hydrocarbon solvent. However, since the trialkylamine, which is the amine compound described in Patent Document 4, has a high basicity and is also nucleophilic, there is a concern that it may become a catalyst poison for the polymerization reaction of olefins and dienes.

[0009] Prior Art Documents

[0010] Patent Documents

[0011] Patent Document 1: Japanese Patent Application Laid-Open No. 2018-104335

[0012] Patent Document 2: Japanese Patent Application Laid-Open No. 2000-507157

[0013] Patent Document 3: Japanese Patent Application Laid-Open No. 2007-530673

[0014] Patent Document 4: Japanese Patent Application Laid-Open No. 2019-59795 Summary of the Invention

[0015] Problems to be Solved by the Invention

[0016] In view of these prior arts, the present invention provides a borate compound-containing composition that is soluble in a hydrocarbon solvent, particularly an aliphatic hydrocarbon solvent, and does not become a catalyst poison for the polymerization reaction of olefins and dienes, and an industrial production method thereof.

[0017] Means for Solving the Problems

[0018] The present inventors conducted intensive studies and, as a result, first found that the following composition (hereinafter, also referred to as "the composition of the present invention") is soluble in a hydrocarbon solvent, particularly an aliphatic hydrocarbon solvent, and does not produce a compound that becomes a catalyst poison for the polymerization reaction of olefins and dienes, and is useful as a cocatalyst, and thus completed the present invention. The composition contains a compound represented by the following formula (1) and a compound represented by the following formula (4).

[0019]

[0020] [In the formula,

[0021] R 1 、R2 , R 3 and R 4 each independently represents a C 1-4 aryl substituted with one or more fluorine atoms or one or more fluorinated C 6-14 alkyl groups,

[0022] A + represents a hydrogen ion (H + ), a cation having 25 or more carbon atoms in total represented by the formula (2), or a cation having 25 or more carbon atoms in total represented by the formula (3),

[0023]

[0024] (In the formula, R 5 , R 6 and R 7 each independently represents an optionally substituted C 1-30 alkyl group or an optionally substituted C 6-14 aryl group.)

[0025]

[0026] (In the formula, Ar 1 , Ar 2 and Ar 3 each independently represents a C 1-30 aryl group optionally substituted with one or more C 1-30 alkyl groups or C 6-14 alkoxy groups.)

[0027] Moreover, R and R' each independently represent an optionally substituted C 1-30 alkyl group, an optionally substituted C 3-15 cycloalkyl group, or an optionally substituted C 6-14 aryl group.

[0028] Among them, when A + is a hydrogen ion (H + ), the total carbon number of R and R' is 20 or more, and with respect to 1 mole of the compound represented by the aforementioned formula (1), the content of the compound represented by the aforementioned formula (4) is 2 moles or more,

[0029] When A + is a cation represented by the formula (2) or a cation represented by the formula (3), the total carbon number of R and R' is 8 or more.

[0030] That is, the present invention is as follows.

[0031] [1] A composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4),

[0032]

[0033] [Wherein,

[0034] R 1 , R 2 , R 3 and R 4 each independently represents a C 1-4 Alkyl substituted C 6-14 Aryl,

[0035] A + Represents hydrogen ion (H + ), a cation having a total carbon number of 25 or more represented by formula (2), or a cation having a total carbon number of 25 or more represented by formula (3),

[0036]

[0037] (Where R 5 , R 6 and R 7 Each independently represents an optionally substituted C 1-30 Alkyl or optionally substituted C 6-14 Aryl. )

[0038]

[0039] (Where Ar 1 ,Ar 2 and Ar 3 Each independently represents one or more C 1-30 Alkyl or C 1-30 Alkoxy substituted C 6-14 aryl. ), and

[0040] R and R' each independently represent an optionally substituted C 1-30 Alkyl, optionally substituted C 3-15 Cycloalkyl or optionally substituted C 6-14 Aryl.

[0041] Among them, A + For hydrogen ions (H + ), the total number of carbon atoms of R and R' is 20 or more, and the content of the compound represented by the above formula (4) is 2 mol or more relative to 1 mol of the compound represented by the above formula (1),

[0042] A + When it is a cation represented by formula (2) or a cation represented by formula (3), the total number of carbon atoms of R and R' is 8 or more. ].

[0043] [2] The composition according to [1], wherein R and R' are each independently C1-30 An alkyl group or an optionally substituted C 6-14 aryl group, and

[0044] the total carbon number of R and R' is 25 or more when A + is a hydrogen ion (H + ), and is 8 or more when A + is the cation represented by formula (2) or the cation represented by formula (3).

[0045] [3] The composition according to the foregoing [1] or [2], wherein R 1 , R 2 , R 3 and R 4 are each independently a group substituted with one or more fluorine atoms or trifluoromethyl groups, respectively: phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 9-phenanthryl or 3-phenanthryl.

[0046] [4] The composition according to the foregoing [1] or [2], wherein R 1 , R 2 , R 3 and R 4 are all pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl.

[0047] [5] The composition according to any one of the foregoing [1] to [4], wherein A + is a hydrogen ion.

[0048] [6] The composition according to any one of the foregoing [1] to [4], wherein A + is the cation having 35 or more carbon atoms represented by the foregoing formula (2), and

[0049] R 5 , R 6 and R 7 are each independently a C 1-30 alkyl group, or a C 6-14 aryl group optionally substituted with a substituent selected from the group consisting of the following groups:

[0050] (1) A halogen atom,

[0051] (2) A C 1-30 alkyl group,

[0052] (3) A C 1-30 alkoxy group, and

[0053] (4) Halo C 1-30 alkyl group.

[0054] [7] The composition according to any one of the foregoing [1] to [4], wherein A + is a cation having 35 or more carbon atoms in total represented by the foregoing formula (2),

[0055] R 5 is C optionally substituted with a substituent selected from the group consisting of the following groups 6-14 aryl group:

[0056] (1) A halogen atom,

[0057] (2) C 1-30 alkyl group,

[0058] (3) C 1-30 alkoxy group, and

[0059] (4) Halo C 1-6 alkyl group,

[0060] and R 6 and R 7 are each independently C optionally substituted 1-30 alkyl group.

[0061] [8] The composition according to any one of the foregoing [1] to [4], wherein A + is a cation having 35 or more carbon atoms in total represented by the foregoing formula (2),

[0062] R 5 is C substituted with C 6-14 aryl group or C 1-30 alkyl group substituted with one or more fluorine atoms, the C 1-30 aryl group is substituted with one or more fluorine atoms, and 6-14

[0063] R 6 and R 7 are each independently C optionally substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl group:

[0064] (1) C optionally substituted with a halogen atom 6-14 aryl group,

[0065] (2) A halogen atom, and

[0066] (3) C 1-30 alkoxy group.

[0067] [9] The composition according to any one of the foregoing [1] to [4], wherein A +is a cation with 35 or more carbon atoms in total as shown in the foregoing formula (2),

[0068] R 5 is a fluoro C 1-6 alkyl group, and

[0069] R 6 and R 7 are each independently a C 1-30 alkyl group optionally substituted with a substituent selected from the group consisting of the following groups:

[0070] (1) A C 6-14 aryl group optionally substituted with a halogen atom,

[0071] (2) A halogen atom, and

[0072] (3) A C 1-30 alkoxy group.

[0073]

[10] The composition according to any one of the foregoing [1] to [4], wherein A + is a cation with 35 or more carbon atoms in total as shown in the foregoing formula (3), and

[0074] Ar 1 , Ar 2 and Ar 3 are each independently a phenyl group optionally substituted with a C 1-30 alkyl group or a C 1-30 alkoxy group.

[0075]

[11] The composition according to any one of the foregoing [1] to [4], wherein A + is a hydrogen ion, and

[0076] R and R’ are each independently:

[0077] A C 1-30 alkyl group optionally substituted with a substituent selected from the group consisting of the following groups:

[0078] (1) A halogen atom,

[0079] (2) A C 1-30 alkoxy group, and

[0080] (3) A halogenated C 1-30 alkoxy group;

[0081] A C 3-15 cycloalkyl group optionally substituted with a substituent selected from the group consisting of the following groups:

[0082] (1) A halogen atom,

[0083] (2) A C 1-30 alkyl group,

[0084] (3)C 1-30 alkoxy

[0085] (4)halo-C 1-30 alkyl, and

[0086] (5)halo-C 1-30 alkoxy;

[0087] or C optionally substituted with a substituent selected from the group consisting of the following groups 6-14 aryl:

[0088] (1)a halogen atom,

[0089] (2)C 1-30 alkyl,

[0090] (3)C 1-30 alkoxy,

[0091] (4)halo-C 1-30 alkyl, and

[0092] (5)halo-C 1-30 alkoxy.

[0093]

[12] The composition according to any one of the foregoing [1] to [4], wherein A + is a hydrogen ion, and

[0094] R and R' are each independently C 1-30 alkyl.

[0095]

[13] The composition according to any one of the foregoing [1] to [4], wherein A + is a hydrogen ion,

[0096] R and R' are each independently C 14-30 alkyl, and

[0097] the total carbon number of R and R' is 28 or more.

[0098]

[14] The composition according to any one of the foregoing [1] to [4], wherein A + is a hydrogen ion, and

[0099] R and R' are the same group.

[0100]

[15] The composition according to any one of the foregoing [1] to [4] and [6] to

[10] , wherein A + is the cation represented by the foregoing formula (2) or formula (3), R and R' are each independently C 1-30 alkyl, and the total carbon number of R and R' is 8 or more.

[0101]

[16] According to the composition described in any one of the foregoing [1] to [4], [6] to

[10] , and

[15] , wherein, relative to 1 mole of the compound represented by the foregoing formula (1) (wherein A in the formula + is the cation represented by the foregoing formula (2) or formula (3).), the content of the compound represented by the foregoing formula (4) is in the range of 0.01 to 10 moles.

[0102]

[17] According to the composition described in any one of the foregoing [1] to [4], [6] to

[10] , and

[15] , wherein, relative to 1 mole of the compound represented by the foregoing formula (1) (wherein A in the formula + is the cation represented by the foregoing formula (2) or formula (3).), the content of the compound represented by the foregoing formula (4) is in the range of 0.01 to 3 moles.

[0103]

[18] According to the composition described in any one of the foregoing [1] to

[17] , its solubility at 25 °C in n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, methylcyclohexane, or a mixed solvent thereof is 5 wt% or more.

[0104]

[19] According to the composition described in any one of the foregoing [1] to

[18] , it substantially does not contain ethers having 7 or less carbon atoms in total.

[0105]

[20] A cocatalyst for use in the polymerization of at least one monomer selected from the group consisting of olefins and dienes, the cocatalyst comprising the composition described in any one of the foregoing [1] to

[19] .

[0106]

[21] A method for producing a polymer, comprising: using the composition described in any one of the foregoing [1] to

[19] as a cocatalyst to polymerize at least one monomer selected from the group consisting of olefins and dienes.

[0107]

[22] A production method, characterized in that it is a production method of the following composition, the composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4),

[0108]

[0109]

[0110] [In the formula,

[0111] R 1 、R 2 、R 3 and R 4 each independently represent C substituted by one or more fluorine atoms or one or more fluorinated C 1-4 alkyl - substituted C 6-14Aryl

[0112] A + represents a hydrogen ion (H + ).

[0113] R and R' each independently represent an optionally substituted C 1-30 alkyl group, an optionally substituted C 3-15 cycloalkyl group or an optionally substituted C 6-14 aryl group, and the total carbon number of R and R' is 20 or more, and

[0114] relative to 1 mole of the compound represented by the foregoing formula (1), the content of the compound represented by the foregoing formula (4) is 2 moles or more.] ,

[0115] The production method includes a step of reacting a compound represented by the following formula (5) with a compound represented by the following formula (4),

[0116]

[0117] [In the formula,

[0118] R 1 , R 2 , R 3 and R 4 represent the same meanings as described above,

[0119] R 8 and R 9 each independently represent a C 1-6 alkyl group, and

[0120] R 8 OR 9 the total carbon number of represents 7 or less.]

[0121]

[0122] [R and R' in the formula represent the same meanings as described above.].

[0123]

[23] According to the production method described in the foregoing

[22] , wherein R 8 and R 9 are both ethyl groups.

[0124] Effects of the Invention

[0125] According to the present invention, it is possible to provide a composition containing a borate compound that is soluble in a hydrocarbon solvent, particularly an aliphatic hydrocarbon solvent, and is useful as a cocatalyst for the polymerization reaction of olefins and dienes, and a method for producing the same. Detailed Embodiments

[0126] The terms and definitions of each symbol used in this specification are described below.

[0127] In this specification, "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0128] In this specification, "alkyl (group)" means a linear or branched alkyl group having 1 or more carbon atoms.

[0129] In this specification, "C 1-30 alkyl (group)" means a linear or branched alkyl group having 1 to 30 carbon atoms. For example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, etc. can be mentioned.

[0130] In this specification, "C 4-30 alkyl (group)" means a linear or branched alkyl group having 4 to 30 carbon atoms. For example, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, etc. can be mentioned.

[0131] In this specification, "C 14-30 alkyl (group)" means a linear or branched alkyl group having 14 to 30 carbon atoms. For example, tetradecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, etc. can be mentioned.

[0132] In this specification, "C 1-6"Alkyl (group)" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms. For example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, etc. may be mentioned. Among them, preferably C 1-4 alkyl.

[0133] In this specification, "halogenated C 1-30 alkyl (group)" refers to a group in which one or more hydrogen atoms in the aforementioned "C 1-30 alkyl" group are substituted by halogen atoms. Specifically, for example, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-difluorobutyl, 4,4,4-trifluorobutyl, 2,2-difluoropentyl, 5,5,5-trifluoropentyl, 2,2-difluorohexyl, 6,6,6-trifluorohexyl, etc. may be mentioned. Among them, preferably "halogenated C 1-6 alkyl" in which one or more hydrogen atoms in the aforementioned "C 1-6 alkyl" group are substituted by halogen atoms.

[0134] In this specification, "fluorinated C 1-6 alkyl (group)" refers to a group in which the halogen atom in the aforementioned "halogenated C 1-6 alkyl" group is a fluorine atom. Specifically, for example, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-difluorobutyl, 4,4,4-trifluorobutyl, 2,2-difluoropentyl, 5,5,5-trifluoropentyl, 2,2-difluorohexyl, 6,6,6-trifluorohexyl, etc. may be mentioned. Among them, preferably "fluorinated C 1-4 alkyl (group)" such as difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-difluorobutyl, 4,4,4-trifluorobutyl, etc., more preferably difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, 2,2-difluoropropyl, and particularly preferably trifluoromethyl, 2,2,2-trifluoroethyl.

[0135] In this specification, "cycloalkyl (group)" refers to a cyclic alkyl group. Particularly when the carbon number range is not limited, preferably C3-15 Cycloalkyl, more preferably C 3-8 Cycloalkyl.

[0136] In this specification, "C 3-15 Cycloalkyl (group)" refers to a cyclic alkyl group having 3 to 15 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentadecyl, etc. can be mentioned. "C 3-8 Cycloalkyl (group)" refers to a cyclic alkyl group having 3 to 8 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. can be mentioned. Among them, C 3-6 Cycloalkyl is preferred.

[0137] In this specification, "alkoxy (group)" refers to a group in which a linear or branched alkyl group is bonded to an oxygen atom.

[0138] In this specification, "C 1-30 Alkoxy (group)" refers to a linear or branched alkoxy group having 1 to 30 carbon atoms. For example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, isohexyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, triacontyloxy, etc. can be mentioned.

[0139] In this specification, "C 4-30 Alkoxy (group)" refers to a linear or branched alkoxy group having 4 to 30 carbon atoms. For example, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, isohexyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, triacontyloxy, etc. can be mentioned.

[0140] In this specification, "C 14-30"Alkoxy (group)" refers to a straight-chain or branched alkoxy group having 14 to 30 carbon atoms. For example, tetradecyloxy, hexadecyloxy, octadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, triacontyloxy, etc. can be cited.

[0141] In this specification, "C 1-6 alkoxy (group)" refers to a straight-chain or branched alkoxy group having 1 to 6 carbon atoms. For example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, etc. can be cited. Among them, C 1-4 alkoxy is preferred.

[0142] In this specification, "halo C 1-30 alkoxy (group)" refers to a group in which one or more hydrogen atoms in the aforementioned "C 1-30 alkoxy" group are replaced by halogen atoms. Specifically, for example, difluoromethoxy, trifluoromethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2-difluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2-difluorobutoxy, 4,4,4-trifluorobutoxy, 2,2-difluoropentyloxy, 5,5,5-trifluoropentyloxy, 2,2-difluorohexyloxy, 6,6,6-trifluorohexyloxy, etc. can be cited. Among them, it is preferred that one or more hydrogen atoms in the aforementioned "C 1-6 alkoxy" group are replaced by halogen atoms to form "halo C 1-6 alkoxy".

[0143] In this specification, "fluoro C 1-6 alkoxy (group)" refers to the aforementioned "halo C 1-6A group in which the halogen atom in the "alkoxy" group is a fluorine atom. Specifically, for example, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2-difluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2-difluorobutoxy, 4,4,4-trifluorobutoxy, 2,2-difluoropentoxy, 5,5,5-trifluoropentoxy, 2,2-difluorohexoxy, 6,6,6-trifluorohexoxy, etc. can be cited. Among them, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, pentafluoroethoxy, 2,2-difluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2-difluorobutoxy, 4,4,4-trifluorobutoxy, etc. "Fluorinated C 1-4 alkoxy (group)", more preferably difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2-difluoropropoxy, and particularly preferably trifluoromethoxy, 2,2,2-trifluoroethoxy.

[0144] In this specification, "aryl (group)" refers to a monocyclic or polycyclic (fused) hydrocarbon group that exhibits aromaticity. Specifically, for example, phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthryl, 9-phenanthryl, etc. C 6-14 aryl. Among them, phenyl, 4-biphenyl, 1-naphthyl or 2-naphthyl is preferred.

[0145] In this specification, "nitrogen-containing aromatic heterocyclic compound" is a monocyclic or fused polycyclic aromatic heterocyclic compound that contains 1 to 4 heteroatoms selected from nitrogen atom, sulfur atom and oxygen atom as ring-constituting atoms, and refers to a compound that contains at least 1 nitrogen atom as a ring-constituting atom.

[0146] As suitable examples of the "nitrogen-containing aromatic heterocyclic compound", for example, 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compounds such as pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, triazole, tetrazole, triazine, etc.; 8- to 14-membered fused polycyclic (preferably 2- or 3-ring) nitrogen-containing aromatic heterocyclic compounds such as benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzisothiazole, benzotriazole, imidazopyridine, thiophenopyridine, furanopyridine, pyrrolopyridine, pyrazolopyridine, oxazolopyridine, thiazolopyridine, imidazopyrazine, imidazopyrimidine, thiophenopyrimidine, furanopyrimidine, pyrrolopyrimidine, pyrazolopyrimidine, oxazolopyrimidine, thiazolopyrimidine, pyrazolotriazine, indole, isoindole, 1H-indazole, purine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, β-carboline, phenanthridine, acridine, phenazine, phenothiazine, phenoxazine, etc. Among them, 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compounds are preferred, and pyridine or imidazole is more preferred.

[0147] In this specification, "optionally substituted" means unsubstituted or having one or more substituents. As the "substituent", as long as there is no special description, (1) a halogen atom, (2) a nitro group, (3) a cyano group, (4) a C 1-30 alkyl group, (5) a halogenated C 1-30 alkyl group, (6) a C 3-8 cycloalkyl group, (7) a C 1-30 alkoxy group, (8) a halogenated C 1-30 alkoxy group, (9) a C 6-14 aryl group, etc. Among them, a halogen atom, a cyano group, a C 1-6 alkyl group, a halogenated C 1-6 alkyl group, a C 1-6 alkoxy group, a halogenated C 1-6 alkoxy group or a phenyl group are preferred, and a halogen atom (e.g., a fluorine atom), a C 1-6 alkyl group (e.g., a methyl group, an ethyl group), a C 1-6 alkoxy group (e.g., a methoxy group, an ethoxy group) or a halogenated C 1-6 alkyl group (e.g., a trifluoromethyl group) are more preferred. In addition, when there are multiple substituents, each substituent is optionally the same or different. In addition, the above substituents are also optionally substituted by one or more C 1-6 alkyl groups, C 1-6 alkoxy groups, halogen atoms, phenyl groups, etc.

[0148] In this specification, the "hydrocarbon solvent" means a solvent containing an aromatic hydrocarbon solvent and / or an aliphatic hydrocarbon solvent. Among them, from the viewpoints of odor and toxicity, an aliphatic hydrocarbon solvent is preferred.

[0149] In this specification, examples of the "aromatic hydrocarbon solvent" include benzene, toluene, xylene, and the like.

[0150] In this specification, examples of the "aliphatic hydrocarbon solvent" include n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, methylcyclohexane, their mixed solvents, and the like.

[0151] In this specification, "soluble in a hydrocarbon solvent (or an aliphatic hydrocarbon solvent)" means that in a solution of the hydrocarbon solvent (or aliphatic hydrocarbon solvent) and the composition of the present invention at 25°C, the composition of the present invention is dissolved at a concentration of 5% by weight or more to form a transparent and homogeneous solution. Further, "easily soluble in a hydrocarbon solvent (or an aliphatic hydrocarbon solvent)" means that in a solution of the hydrocarbon solvent (or aliphatic hydrocarbon solvent) and the composition of the present invention at 25°C, the composition of the present invention is dissolved at a concentration of 20% by weight or more (preferably 30% by weight or more) to form a transparent and homogeneous solution.

[0152] (The composition of the present invention)

[0153] Hereinafter, the composition of the present invention will be described.

[0154] The composition of the present invention is a composition containing the compound represented by the following formula (1) and the compound represented by the following formula (4).

[0155]

[0156]

[0157] [In the formula,

[0158] R 1 、R 2 、R 3 and R 4 each independently represent an aryl group substituted with one or more fluorine atoms or one or more fluorinated C 1-4 alkyl groups. 6-14

[0159] A + represents a hydrogen ion (H + ), a cation having 25 or more carbon atoms represented by formula (2), or a cation having 25 or more carbon atoms represented by formula (3).

[0160]

[0161] (In the formula, R 5 、R 6 and R 7 each independently represent an optionally substituted C 1-30 alkyl group or an optionally substituted C 6-14 aryl group.)

[0162]

[0163] (In the formula, Ar 1 , Ar 2 and Ar 3 each independently represent an optionally C-substituted by one or more 1-30 alkyl or C 1-30 alkoxy-substituted C 6-14 aryl. ), and

[0164] R and R' each independently represent an optionally substituted C 1-30 alkyl, an optionally substituted C 3-15 cycloalkyl or an optionally substituted C 6-14 aryl.

[0165] Among them, when A + is a hydrogen ion (H + ), the total carbon number of R and R' is 20 or more, and relative to 1 mole of the compound represented by the foregoing formula (1), the content of the compound represented by the foregoing formula (4) is 2 moles or more,

[0166] When A + is the cation represented by the formula (2) or the cation represented by the formula (3), the total carbon number of R and R' is 8 or more. ].

[0167] The composition containing the compound represented by the foregoing formula (1) and the compound represented by the foregoing formula (4) is not particularly limited as long as it contains two compounds, and may also contain a compound in which the compound represented by the foregoing formula (1) coordinates with the compound represented by the foregoing formula (4) to form a complex. The composition of the present invention is preferably a composition containing a complex formed by the compound represented by the foregoing formula (1) and the compound represented by the foregoing formula (4).

[0168] The preferred mode of the compound represented by the formula (1) (hereinafter, "also referred to as compound (1)".) is described below.

[0169] Hereinafter, each group of compound (1) is described.

[0170] R 1 , R 2 , R 3 and R 4 are preferably each independently one or more fluorine atoms or one or more fluoro C 1-4An alkyl group (such as trifluoromethyl) - substituted following groups: phenyl, 1 - naphthyl, 2 - naphthyl, 2 - biphenyl, 3 - biphenyl, 4 - biphenyl, 1 - anthryl, 2 - anthryl, 9 - anthryl, 3 - phenanthryl or 9 - phenanthryl, more preferably each independently is a following group substituted by one or more fluorine atoms or one or more trifluoromethyl groups: phenyl, 1 - naphthyl, 2 - naphthyl or 4 - biphenyl, particularly preferably R 1 , R 2 , R 3 and R 4 are all the same and are pentafluorophenyl, 2,2’,3,3’,4’,5,5’,6,6’ - nonafluoro - 4 - (1,1’ - biphenyl)yl, 2,3,4,5,6,7,8 - heptafluoro - 1 - naphthyl or 1,3,4,5,6,7,8 - heptafluoro - 2 - naphthyl.

[0171] A + is preferably a hydrogen ion (H + ).

[0172] As another preferred form of A + , it is a cation with a total carbon number of 25 or more shown in the aforementioned formula (2), preferably a cation with a total carbon number of 35 or more.

[0173] R 5 , R 6 and R 7 in formula (2) are preferably each independently a C 1-30 alkyl group, or a C 6-14 aryl group optionally substituted by a substituent selected from the group consisting of the following groups:

[0174] (1) A halogen atom,

[0175] (2) A C 1-30 alkyl group,

[0176] (3) A C 1-30 alkoxy group, and

[0177] (4) A halo - C 1-30 alkyl group,

[0178] More preferably, R 5 is a C 6-14 aryl group optionally substituted by a substituent selected from the group consisting of the following groups:

[0179] (1) A halogen atom,

[0180] (2) A C 1-30 alkyl group,

[0181] (3) A C 1-30 alkoxy group, and

[0182] (4) A halo - C1-30 Alkyl

[0183] R 6 and R 7 each independently is an optionally substituted C 1-30 alkyl

[0184] As another preferred embodiment of A + is a cation having 35 or more carbon atoms in total represented by the aforementioned formula (2), and R 5 in the aforementioned formula (2) is a C 6-14 alkyl substituted with an aryl, or a C 1-30 alkyl substituted with one or more fluorine atoms, wherein the C 1-30 aryl is substituted with one or more fluorine atoms, and R 6-14 and R 6 each independently is a C 7 alkyl optionally substituted with a substituent selected from the group consisting of the following groups: 1-30 alkyl:

[0185] (1) An optionally halogen-substituted C 6-14 aryl,

[0186] (2) A halogen atom, and

[0187] (3) A C 1-30 alkoxy

[0188] More preferably, R 5 is a fluorinated C 1-6 alkyl, and R 6 and R 7 each independently is a C 1-30 alkyl optionally substituted with a substituent selected from the group consisting of the following groups:

[0189] (1) An optionally halogen-substituted C 6-14 aryl,

[0190] (2) A halogen atom, and

[0191] (3) A C 1-30 alkoxy

[0192] As another preferred embodiment of A + is a cation having 35 or more carbon atoms in total represented by the aforementioned formula (3),

[0193] wherein, preferably, Ar 1 , Ar 2 and Ar 3 each independently is a phenyl optionally substituted with a C 1-30 alkyl or a C 1-30 alkoxy, more preferably Ar1 、Ar 2 and Ar 3 are each independently a phenyl group optionally substituted with a C 4-30 alkyl group.

[0194] Examples of suitable compound (1) include the following compounds.

[0195] [Compound (1-1)]

[0196] A compound (1), wherein

[0197] R 1 、R 2 、R 3 and R 4 are each independently a group selected from the following groups substituted with one or more fluorine atoms or fluorinated C 1-4 alkyl groups (e.g., trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthryl or 9-phenanthryl, and

[0198] A + is a hydrogen ion (H + ).

[0199] [Compound (1-2-A)]

[0200] A compound (1), wherein

[0201] R 1 、R 2 、R 3 and R 4 are each independently a group selected from the following groups substituted with one or more fluorine atoms or one or more fluorinated C 1-4 alkyl groups (e.g., trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthryl or 9-phenanthryl, and

[0202] A + is a cation having 25 or more carbon atoms represented by the aforementioned formula (2), and R 5 、R 6 and R 7 are each independently a C 1-30 alkyl group, or a C 6-14 aryl group optionally substituted with a substituent selected from the group consisting of the following groups:

[0203] (1) A halogen atom,

[0204] (2) A C 1-30 alkyl group,

[0205] (3)C 1-30 alkoxy, and

[0206] (4) halo C 1-30 alkyl.

[0207] [Compound (1-2)]

[0208] A compound (1), wherein in the aforementioned formula (1),

[0209] R 1 , R 2 , R 3 and R 4 are each independently a group substituted with one or more fluorine atoms or one or more fluorinated C 1-4 alkyl (such as trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthryl or 9-phenanthryl, and

[0210] A + is a cation having 35 or more carbon atoms in total represented by the aforementioned formula (2), and R 5 , R 6 and R 7 are each independently C 1-30 alkyl, or C 6-14 aryl optionally substituted with a substituent selected from the group consisting of the following groups:

[0211] (1) a halogen atom,

[0212] (2) C 1-30 alkyl,

[0213] (3) C 1-30 alkoxy, and

[0214] (4) halo C 1-30 alkyl.

[0215] [Compound (1-2-B)]

[0216] A compound (1), wherein in the aforementioned formula (1),

[0217] R 1 , R 2 , R 3 and R 4 are each independently a group substituted with one or more fluorine atoms or one or more fluorinated C 1-4An alkyl group (such as trifluoromethyl) - substituted following groups: phenyl, 1 - naphthyl, 2 - naphthyl, 2 - biphenyl, 3 - biphenyl, 4 - biphenyl, 1 - anthryl, 2 - anthryl, 9 - anthryl, 3 - phenanthryl or 9 - phenanthryl (preferably phenyl, 1 - naphthyl, 2 - naphthyl or 4 - biphenyl), and

[0218] A + is a cation having a total carbon number of 25 or more (preferably 35 or more) as shown in the foregoing formula (2), and R in formula (2) 5 is a C optionally substituted with a substituent selected from the group consisting of the following groups 6-14 aryl:

[0219] (1) a halogen atom,

[0220] (2) C 1-30 alkyl,

[0221] (3) C 1-30 alkoxy, and

[0222] (4) halo - C 1-30 alkyl

[0223] R 6 and R 7 are each independently an optionally substituted C 1-30 alkyl.

[0224] [Compound (1 - 2 - C)]

[0225] A compound (1), wherein, in the foregoing formula (1)

[0226] R 1 、R 2 、R 3 and R 4 are each independently a group substituted with one or more fluorine atoms or one or more fluoro - C 1-4 alkyl (such as trifluoromethyl) - substituted following groups: phenyl, 1 - naphthyl, 2 - naphthyl, 2 - biphenyl, 3 - biphenyl, 4 - biphenyl, 1 - anthryl, 2 - anthryl, 9 - anthryl, 3 - phenanthryl or 9 - phenanthryl (preferably phenyl, 1 - naphthyl, 2 - naphthyl or 4 - biphenyl), and

[0227] A + is a cation having a total carbon number of 25 or more (preferably 35 or more) as shown in the foregoing formula (2), and R in formula (2) 5 is a C substituted with C 6-14 aryl, or a C substituted with one or more fluorine atoms 1-30 alkyl, and the C 1-30 aryl is substituted with one or more fluorine atoms, and R 6-14 and R 6 and R7 Each independently is a C optionally substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl group:

[0228] (1) C optionally substituted with a halogen atom 6-14 aryl group,

[0229] (2) halogen atom, and

[0230] (3) C 1-30 alkoxy group.

[0231] [Compound (1-2-D)]

[0232] A compound (1), wherein, in the aforementioned formula (1)

[0233] R 1 , R 2 , R 3 and R 4 each independently is the following group substituted with one or more fluorine atoms or one or more fluorinated C 1-4 alkyl group (such as trifluoromethyl): phenyl group, 1-naphthyl group, 2-naphthyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 3-phenanthryl group or 9-phenanthryl group (preferably phenyl group, 1-naphthyl group, 2-naphthyl group or 4-biphenyl group), and

[0234] A + is a cation having a total carbon number of 25 or more (preferably 35 or more) represented by the aforementioned formula (2), R in formula (2) 5 is a fluorinated C 1-6 alkyl group, and R 6 and R 7 each independently is a C optionally substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl group:

[0235] (1) C optionally substituted with a halogen atom 6-14 aryl group,

[0236] (2) halogen atom, and

[0237] (3) C 1-30 alkoxy group.

[0238] [Compound (1-3)]

[0239] A compound (1), wherein, in the aforementioned formula (1)

[0240] R 1 , R 2 , R 3 and R 4Each independently is a group substituted by one or more fluorine atoms or one or more fluorinated C 1-4 alkyl groups (such as trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthryl or 9-phenanthryl, and

[0241] A + is a cation with a total carbon number of 35 or more represented by the aforementioned formula (3), and Ar in formula (3) 1 、Ar 2 and Ar 3 are each independently a phenyl cation optionally substituted by C 1-30 alkyl or C 1-30 alkoxy.

[0242] [Compound (1-4)]

[0243] A compound (1), wherein R in the aforementioned formula (1) 1 、R 2 、R 3 and R 4 are each independently a group substituted by one or more fluorine atoms or one or more trifluoromethyl groups: phenyl, 1-naphthyl, 2-naphthyl or 4-biphenyl, and

[0244] A + is a hydrogen ion (H + ).

[0245] [Compound (1-5)]

[0246] A compound (1), wherein R in the aforementioned formula (1) 1 、R 2 、R 3 and R 4 are each independently a group substituted by one or more fluorine atoms or one or more trifluoromethyl groups: phenyl, 1-naphthyl, 2-naphthyl or 4-biphenyl, and

[0247] A + is a cation with a total carbon number of 35 or more represented by the aforementioned formula (2), and any one of R 5 、R 6 and R 7 in formula (2) is a phenyl optionally substituted by a substituent selected from the group consisting of:

[0248] (1) a halogen atom,

[0249] (2) C 1-30 alkyl,

[0250] (3) C 1-30Alkoxy, and

[0251] (4) Halo C 1-30 alkyl,

[0252] Two of the others are C 1-30 alkyl (preferably C 14-30 alkyl).

[0253] [Compound (1-6)]

[0254] A compound (1), wherein R in the aforementioned formula (1) 1 , R 2 , R 3 and R 4 are each independently a group substituted with one or more fluorine atoms or one or more trifluoromethyl groups: phenyl, 1-naphthyl, 2-naphthyl, or 4-biphenyl, and

[0255] A + is a cation having a total carbon number of 35 or more represented by the aforementioned formula (3), and Ar in the formula (3) 1 , Ar 2 and Ar 3 are each independently a phenyl group optionally substituted with C 4-30 alkyl.

[0256] [Compound (1-7)]

[0257] A compound (1), R in the aforementioned formula (1) 1 , R 2 , R 3 and R 4 are all the same and are pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl) group, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group, and

[0258] A + is a hydrogen ion (H + ).

[0259] [Compound (1-8)]

[0260] A compound (1), wherein R in the aforementioned formula (1) 1 , R 2 , R 3 and R 4 are all the same and are pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl) group, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group, and

[0261] A + is a cation having 35 or more carbon atoms as shown in the foregoing formula (2), and R in formula (2) 5 , R 6 , and R 7 any one of which is a phenyl group optionally substituted with a substituent selected from the group consisting of the following groups:

[0262] (1) a halogen atom,

[0263] (2) C 1-30 alkyl,

[0264] (3) C 1-30 alkoxy, and

[0265] (4) halo C 1-30 alkyl

[0266] the other two of which are C 1-30 alkyl (preferably C 14-30 alkyl).

[0267] [Compound (1-9)]

[0268] A compound (1), wherein

[0269] R 1 , R 2 , R 3 , and R 4 are all the same and are pentafluorophenyl, 2,2’,3,3’,4’,5,5’,6,6’-nonafluoro-4-(1,1’-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl, and

[0270] A + is a cation having 35 or more carbon atoms as shown in the foregoing formula (3), and Ar in formula (3) 1 , Ar 2 , and Ar 3 are each independently a phenyl group optionally substituted with C 4-30 alkyl.

[0271] As preferred specific examples of the compound (1), for example, hydrotetrakis(pentafluorophenyl)borate, hydrotetrakis(heptafluoronaphthyl)borate, hydrotetrakis(nonafluorobiphenyl)borate, N,N-dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecylaniline tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-(2,3,4,5,6-pentafluorophenyl)methylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2,3,3,3-pentafluoropropylammonium tetrakis(pentafluorophenyl)borate, N,N-didodecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2-difluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-3,3,3-trifluoropropylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2-fluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-didocosyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-bis(3,7,11,15-tetramethylhexadecyl)-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-bis(3,7,11-trimethyldodecyl)-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-ditetradecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-dipalmitoyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(heptafluoronaphthyl)borate, N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(nonafluorobiphenyl)borate, etc. can be mentioned.

[0272] The preferred modes of the compound represented by the formula (4) (hereinafter, also referred to as "compound (4)") will be described below.

[0273] Each group of the compound (4) will be described below.

[0274] The preferred mode of the compound (4) depends on A in the compound (1) + and varies depending on the type.

[0275] A in the compound (1) + is a hydrogen ion (H + ),

[0276] the total carbon number of R and R' is 20 or more, preferably 25 or more, more preferably 28 or more, and further preferably 30 or more.

[0277] R and R' are each independently an optionally substituted C 1-30 alkyl group, an optionally substituted C 3-15 cycloalkyl group or an optionally substituted C6-14 An aryl group, preferably each independently a C optionally substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl groups:

[0278] (1) A halogen atom,

[0279] (2) A C 1-30 alkoxy group,

[0280] (3) A halo C 1-30 alkoxy group;

[0281] A C optionally substituted with a substituent selected from the group consisting of the following groups 3-15 cycloalkyl group:

[0282] (1) A halogen atom,

[0283] (2) A C 1-30 alkyl group,

[0284] (3) A C 1-30 alkoxy group,

[0285] (4) A halo C 1-30 alkyl group,

[0286] (5) A halo C 1-30 alkoxy group

[0287] or a C optionally substituted with a substituent selected from the group consisting of the following groups 6-14 aryl group:

[0288] (1) A halogen atom,

[0289] (2) A C 1-30 alkyl group,

[0290] (3) A C 1-30 alkoxy group,

[0291] (4) A halo C 1-30 alkyl group,

[0292] (5) A halo C 1-30 alkoxy group,

[0293] More preferably, each independently is 1-30 an alkyl group, or a C optionally substituted with a substituent selected from the group consisting of the following groups 6-14 aryl group:

[0294] (1) A halogen atom,

[0295] (2) A C 1-30 alkyl group,

[0296] (3) A C 1-30 alkoxy group,

[0297] (4) Halo-C 1-30 alkyl,

[0298] (5) Halo-C 1-30 alkoxy

[0299] More preferably, each is independently C 14-30 alkyl.

[0300] When A in compound (1) + is the cation shown in formula (2) or the cation shown in formula (3), the total carbon number of R and R' is preferably 8 or more, more preferably 10 or more.

[0301] R and R' are preferably each independently C 1-30 alkyl.

[0302] As A in compound (1) + is a hydrogen ion (H + ), suitable compounds (4) include the following compounds.

[0303] [Compound (4-1-A)]

[0304] A compound (4), wherein

[0305] R and R' are each independently C optionally substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl:

[0306] (1) A halogen atom,

[0307] (2) C 1-30 alkoxy, and

[0308] (3) Halo-C 1-30 alkoxy;

[0309] C optionally substituted with a substituent selected from the group consisting of the following groups 3-15 cycloalkyl:

[0310] (1) A halogen atom,

[0311] (2) C 1-30 alkyl,

[0312] (3) C 1-30 alkoxy,

[0313] (4) Halo-C 1-30 alkyl, and

[0314] (5) Halo-C 1-30 alkoxy;

[0315] or optionally C substituted with a substituent selected from the group consisting of the following groups 6-14 aryl:

[0316] (1) a halogen atom,

[0317] (2) C 1-30 alkyl,

[0318] (3) C 1-30 alkoxy,

[0319] (4) halo C 1-30 alkyl, and

[0320] (5) halo C 1-30 alkoxy,

[0321] and

[0322] the total carbon number of R and R' is 20 or more (preferably 25 or more).

[0323] [Compound (4-1-B)]

[0324] A compound (4), wherein in the aforementioned formula (4)

[0325] R and R' are each independently C 1-30 alkyl, or optionally C substituted with a substituent selected from the group consisting of the following groups 6-14 aryl:

[0326] (1) a halogen atom,

[0327] (2) C 1-30 alkyl,

[0328] (3) C 1-30 alkoxy,

[0329] (4) halo C 1-30 alkyl, and

[0330] (5) halo C 1-30 alkoxy,

[0331] and

[0332] the total carbon number of R and R' is 20 or more (preferably 25 or more).

[0333] [Compound (4-1-C)]

[0334] A compound (4), wherein in the aforementioned formula (4)

[0335] R and R' are each independently C 1-30 alkyl, and

[0336] The total carbon number of R and R’ is 20 or more (preferably 25 or more).

[0337] [Compound (4-1)]

[0338] A compound (4), wherein in the aforementioned formula (4),

[0339] R and R’ are each independently a C 14-30 alkyl group, and

[0340] the total carbon number of R and R’ is 28 or more.

[0341] As A in compound (1) + is a hydrogen ion (H + ), preferred specific examples of compound (4) include, for example, didecyl ether, didodecyl ether, ditetradecyl ether, dihexadecyl ether, dioctadecyl ether, docosyl ethyl ether, tetradecyloxyethyl tetradecyl ether, etc.

[0342] As A in compound (1) + is a cation represented by formula (2) or a cation represented by formula (3), suitable compounds (4) include the following compounds.

[0343] [Compound (4-2)]

[0344] A compound (4), wherein in the aforementioned formula (4),

[0345] R and R’ are each independently a C 1-30 alkyl group, and

[0346] the total carbon number of R and R’ is 8 or more.

[0347] [Compound (4-3)]

[0348] A compound (4), wherein in the aforementioned formula (4),

[0349] R and R’ are each independently a C 1-30 alkyl group, and

[0350] the total carbon number of R and R’ is 10 or more.

[0351] As A in compound (1) + is a cation represented by formula (2) or a cation represented by formula (3), preferred specific examples of compound (4) include, for example, dibutyl ether, dihexyl ether, dioctyl ether, didecyl ether, didodecyl ether, ditetradecyl ether, dihexadecyl ether, dioctadecyl ether, cyclopentyl methyl ether, diphenyl ether, octadecyl phenyl ether, etc., among which, didodecyl ether, ditetradecyl ether, dihexadecyl ether, dioctadecyl ether are preferred.

[0352] When the total carbon number of the groups R and R' in compound (4) is 7 or less, the boiling point is low, so there is a concern that it may be difficult to control its content industrially.

[0353] As suitable combinations of compound (1) and compound (4) contained in the composition of the present invention, specifically, for example, combinations of compound (1-1) and compound (4-1), compound (1-2) and compound (4-2), compound (1-3) and compound (4-2), compound (1-4) and compound (4-1), compound (1-5) and compound (4-3), compound (1-6) and compound (4-3), compound (1-7) and compound (4-1), compound (1-8) and compound (4-3), compound (1-9) and compound (4-3), compound (1-2-A) and compound (4-2), compound (1-2-B) and compound (4-2), compound (1-2-C) and compound (4-2), compound (1-2-D) and compound (4-1), compound (1-2-D) and compound (4-2), compound (1-2-D) and compound (4-1-C), etc. can be cited.

[0354] In the composition of the present invention, the suitable content range of compound (4) relative to 1 mole of compound (1) varies depending on the type of A + in compound (1).

[0355] A in compound (1) + is a hydrogen ion (H + )), the content of compound (4) is 2 moles or more, preferably 2 to 3 moles, relative to 1 mole of compound (1).

[0356] A in compound (1) + is the cation represented by formula (2) or the cation represented by formula (3), the content of compound (4) is usually 0.01 to 10 moles, preferably 0.01 to 3 moles, relative to 1 mole of compound (1).

[0357] Here, the content of compound (4) relative to 1 mole of compound (1) corresponds to the input amounts of the respective compounds during production when A + in compound (1) is any one of a hydrogen ion (H + ), the cation represented by formula (2), or the cation represented by formula (3).

[0358] The composition of the present invention is soluble in hydrocarbon solvents at room temperature (15 to 30 °C). In addition, conventionally known borate compounds (for example, tetrakis(pentafluorophenyl)borate hydride, tetrakis(pentafluorophenyl)borate ether complex, lithium tetrakis(pentafluorophenyl)borate, etc.) are insoluble in aliphatic hydrocarbon solvents such as hexane, and can be catalyst poisons for metal catalysts used in the polymerization reactions of olefins and dienes that can form a homogeneous system. However, the composition of the present invention also shows good solubility in aliphatic hydrocarbon solvents and does not become a catalyst poison. Therefore, it is useful as a cocatalyst for the polymerization reactions of olefins and dienes in a homogeneous system.

[0359] (Method for producing the composition of the present invention)

[0360] Hereinafter, the method for producing the composition of the present invention will be described.

[0361] The composition of the present invention substantially does not contain ether compounds (for example, diethyl ether, etc.) having 7 or less carbon atoms in total that can become catalyst poisons. Substantially not containing ether compounds having 7 or less carbon atoms in total means that 1 as a result of 1H-NMR analysis, ether compounds having 7 or less carbon atoms in total are not detected.

[0362] The method for producing the composition of the present invention is not particularly limited. The composition of the present invention can be produced, for example, according to the following Production Method 1 to Production Method 4.

[0363] (Production Method 1) (The composition of the present invention containing a compound (1a) + wherein A is a hydrogen ion (H + ))

[0364] Production Method 1 is a method for obtaining the composition of the present invention containing the compound (1a) and the compound (4) (or a complex of the compound (1a) and the compound (4)) by reacting the compound (5) with a protonic acid in a solvent that does not affect the reaction in the presence of the compound (4).

[0365]

[0366] (In the formula, M + represents a metal ion (for example, lithium ion, potassium ion, sodium ion, etc.), n represents a number of 2 or more, and the definitions of the other symbols are the same as those described above.

[0367] There is no particular limitation on the reaction solvent for this reaction. For example, aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform, dichloromethane, and 1,2-dichloroethane, aliphatic hydrocarbons such as hexane, isohexane, heptane, octane, and methylcyclohexane, or mixtures thereof can be mentioned. Among them, dichloromethane or 1,2-dichloroethane, hexane, isohexane, heptane, octane, and methylcyclohexane are preferred.

[0368] In this preparation method, for the compound (5) used as a raw material, examples of the compound obtained by substituting A in the aforementioned formula (1) + with M + include metal salts. As the compound (5), commercially available products, purified products, or substances prepared by known methods can be used. Specific examples of the compound (5) include lithium tetrakis(pentafluorophenyl)borate, potassium tetrakis(pentafluorophenyl)borate, lithium tetrakis(heptafluoronaphthyl)borate, potassium tetrakis(heptafluoronaphthyl)borate, chloromagnesium tetrakis(pentafluorophenyl)borate, chloromagnesium tetrakis(heptafluoronaphthyl)borate, bromomagnesium tetrakis(pentafluorophenyl)borate, bromomagnesium tetrakis(heptafluoronaphthyl)borate, lithium tetrakis(nonafluorobiphenyl)borate, potassium tetrakis(nonafluorobiphenyl)borate, chloromagnesium tetrakis(nonafluorobiphenyl)borate, bromomagnesium tetrakis(nonafluorobiphenyl)borate, etc.

[0369] As the compound (4) used in this preparation method, for example, the aforementioned compound (4-1), compound (4-2), etc. can be cited.

[0370] The amount of the compound (4) used is 2 moles or more, preferably 2 - 3 moles, relative to 1 mole of the compound (5).

[0371] Examples of the protonic acid used in this preparation method include hydrogen chloride, hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, hydroiodic acid, etc. Among them, hydrochloric acid and hydrogen chloride-ether solution are preferred.

[0372] When the amount of the protonic acid used is equivalent or more relative to 1 mole of the compound (5), there are no particular problems. Preferably, the organic phase is washed with water until the pH of the washed aqueous phase is 3 or more so that the used protonic acid does not remain in the organic phase after treatment. When the pH of the aqueous phase is less than 3, there is a concern that the protonate used in the organic phase remains in the composition of the present invention, thereby becoming a catalyst poison during polymerization.

[0373] The reaction temperature is usually 0°C to 40°C, preferably 10°C to 35°C, more preferably room temperature (15°C to 30°C), and the reaction time is usually about 10 minutes to 10 hours, preferably about 1 to 3 hours.

[0374] (Preparation method 2) (Method for producing the composition of the present invention containing the compound (1a) + wherein A is a hydrogen ion (H + ))

[0375] Preparation method 2 is a method for obtaining the composition of the present invention containing the compound (1a) and the compound (4) (or a complex of the compound (1a) and the compound (4)) by reacting the compound (6) with the compound (4) in a solvent that does not affect the reaction.

[0376]

[0377] (The definitions of the symbols in the formula are the same as those described above.)

[0378] The reaction solvent for this reaction is not particularly limited. For example, aromatic hydrocarbon solvents such as toluene and xylene can be cited; halogenated hydrocarbon solvents such as chloroform, dichloromethane, and 1,2-dichloroethane, aliphatic hydrocarbon solvents such as hexane, isohexane, heptane, octane, and methylcyclohexane, or mixtures thereof. Among them, dichloromethane or 1,2-dichloroethane, hexane, isohexane, heptane, octane, and methylcyclohexane are preferred.

[0379] In this production method, for the compound (6) used as a raw material, commercially available products, or products prepared according to known methods per se (for example, refer to Organometallics, 2000, 19, 1442-1444) or methods based thereon can be used.

[0380] As the compound (4) used in this production method, for example, the aforementioned compound (4-1), compound (4-2), etc. can be cited.

[0381] Relative to 1 mole of the compound (6), the amount of the compound (4) used is usually 2 moles or more, preferably 2 to 3 moles.

[0382] The reaction temperature is usually 0°C to 40°C, preferably 10°C to 35°C, more preferably room temperature (15°C to 30°C), and the reaction time is usually about 10 minutes to 10 hours, preferably about 1 to 3 hours.

[0383] (Production method 3) (A composition of the present invention containing a compound (1b) + as a cation other than a hydrogen ion (H + )) manufacturing method)

[0384] Production method 3 is a method for obtaining a composition of the present invention containing a compound (1b) and a compound (4) by subjecting to the following steps: adding a compound (6) and a compound (7) (for example, an amine deprotonated by the cation shown in the aforementioned formula (2)) to a solvent that does not affect the reaction and suspending them, dropping a protonic acid into the suspension and stirring, then filtering, and concentrating the filtrate under reduced pressure to obtain a compound (1b) (step 1); and, mixing and stirring the compound (1b) and the compound (4) in a solvent that does not affect the reaction (step 2).

[0385]

[0386] (The definitions of the symbols in the formula are the same as those described above.)

[0387] (Step 1)

[0388] Examples of the solvent used in this step include hydrocarbon solvents such as toluene, n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, and methylcyclohexane, or mixtures thereof. Among them, aliphatic hydrocarbon solvents such as n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, and methylcyclohexane are preferred.

[0389] Examples of the compound (7) used in this step include, for example, tertiary amines formed by deprotonating the cations represented by the aforementioned formula (2). Among them, preferred are tertiary amines such as dihydrogenated tallow alkyl methylamine, N,N - distearyl methylamine, N,N - distearyl aniline, N,N - distearyl - 2,2,2 - trifluoroethylamine, N,N - distearyl - (2,3,4,5,6 - pentafluorophenyl)methylamine, N,N - distearyl - 2,2,3,3,3 - pentafluoropropylamine, N,N - dilauryl - 2,2,2 - trifluoroethylamine, N,N - distearyl - 2,2 - difluoroethylamine, N,N - distearyl - 3,3,3 - trifluoropropylamine, N,N - distearyl - 2 - fluoroethylamine, N,N - didodecyl - 2,2,2 - trifluoroethylamine, N,N - bis(3,7,11,15 - tetramethylhexadecyl)-2,2,2 - trifluoroethylamine, N,N - bis(3,7,11 - trimethyldodecyl)-2,2,2 - trifluoroethylamine, N,N - ditetradecyl - 2,2,2 - trifluoroethylamine, N,N - dipalmitoyl - 2,2,2 - trifluoroethylamine, etc.

[0390] The amount of the compound (7) is usually 1 to 10 moles, preferably 1 to 2 moles, relative to 1 mole of the compound (6).

[0391] Examples of the protonic acid used in this step include hydrogen chloride, sulfuric acid, nitric acid, hydrogen bromide, hydrogen iodide, etc. Among them, hydrogen chloride (more preferably hydrogen chloride - ether solution) is preferred.

[0392] When the amount of the protonic acid is equivalent or more relative to 1 mole of the compound (7), there is no particular problem. It is preferred to wash the organic phase with water until the pH of the aqueous phase after washing is 3 or more so that the used protonic acid does not remain in the treated organic phase. When the pH of the aqueous phase is less than 3, there is a concern that the protonate salt used in the organic phase remains in the composition of the present invention, thereby becoming a catalyst poison during polymerization.

[0393] In Production Method 3, the compound (1b) prepared as described above can be directly used in Step 2.

[0394] (Step 2)

[0395] The solvent used in this step is not particularly limited. For example, aliphatic hydrocarbon solvents such as n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, and methylcyclohexane can be cited. Among them, n - hexane is preferred.

[0396] As the compound (4) used in this step, for example, the aforementioned compound (4 - 3), compound (4 - 4), etc. can be cited.

[0397] The amount of the compound (4) used is usually 0.01 - 10 moles, preferably 0.01 - 3 moles, relative to 1 mole of the compound (1b).

[0398] The reaction temperature is usually 0°C - 40°C, preferably 10°C - 35°C, more preferably room temperature (15°C - 30°C), and the reaction time is usually about 10 minutes - 10 hours, preferably about 1 - 3 hours.

[0399] (Production method 4) (The production method of the composition of the present invention containing the compound (1b) which is a cation other than a hydrogen ion (H + )) + )

[0400] Production method 4 is a method for obtaining the composition of the present invention containing the compound (1b) and the compound (4) by subjecting to the following steps: adding the compound (8) and the compound (5) to a solvent that does not affect the reaction and stirring, then filtering the reaction mixture, and concentrating the filtrate under reduced pressure to obtain the compound (1b) (step 1); and, mixing and stirring the compound (1b) and the compound (4) in a solvent that does not affect the reaction (step 2).

[0401]

[0402] (In the formula, X represents a halogen atom, and the definitions of the other symbols are the same as the aforementioned meanings.)

[0403] (Step 1)

[0404] As the solvent used in this step, hydrocarbon solvents such as toluene, n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, methylcyclohexane, and n - heptane, halogen - based solvents such as dichloromethane and chloroform, or mixtures thereof can be cited. Among them, aliphatic hydrocarbon solvents such as n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, and methylcyclohexane are preferred.

[0405] As the compound (8) used in this step, for example, N,N-dioctadecylmethylamine hydrochloride, dihydrotallow alkylmethylamine hydrochloride, N,N-dioctadecylaniline hydrochloride, N,N-dioctadecyl-2,2,2-trifluoroethylamine hydrochloride, N,N-dioctadecyl-(2,3,4,5,6-pentafluorophenyl)methylamine hydrochloride, N,N-dioctadecyl-2,2,3,3,3-pentafluoropropylamine hydrochloride, N,N-didodecyl-2,2,2-trifluoroethylamine hydrochloride, N,N-dioctadecyl-2,2-difluoroethylamine hydrochloride, N,N-dioctadecyl-3,3,3-trifluoropropylamine hydrochloride, N,N-dioctadecyl-2-fluoroethylamine hydrochloride, N,N-didocosyl-2,2,2-trifluoroethylamine hydrochloride, N,N-bis(3,7,11,15-tetramethylhexadecyl)-2,2,2-trifluoroethylamine hydrochloride, N,N-bis(3,7,11-trimethyldodecyl)-2,2,2-trifluoroethylamine hydrochloride, N,N-ditetradecyl-2,2,2-trifluoroethylamine hydrochloride, N,N-dihexadecyl-2,2,2-trifluoroethylamine hydrochloride, tris(p-octylphenyl)chloromethane are preferably used.

[0406] Relative to 1 mole of the compound (5), the amount of the compound (8) used is usually 1 to 2 moles, preferably 1 to 1.1 moles.

[0407] In Preparation Method 4, the compound (1b) prepared as described above can be directly used in Step 2.

[0408] (Step 2)

[0409] The solvent used in this step is not particularly limited. For example, aliphatic hydrocarbon solvents such as n-hexane, isohexane, n-heptane, n-octane, cyclohexane, and methylcyclohexane can be cited. Among them, n-hexane is preferred.

[0410] As the compound (4) used in this step, for example, the aforementioned compound (4-3), compound (4-4), etc. can be cited.

[0411] Relative to 1 mole of the compound (1b), the amount of the compound (4) used is usually 0.01 to 10 moles, preferably 0.01 to 3 moles.

[0412] The reaction temperature is usually 0°C to 40°C, preferably 10°C to 35°C, more preferably room temperature (15°C to 30°C), and the reaction time is usually about 10 minutes to 10 hours, preferably about 1 to 3 hours.

[0413] The composition of the present invention contains compound (1) and compound (4), and substantially does not contain amine compounds that are soluble (or readily soluble) in hydrocarbon solvents, especially aliphatic hydrocarbon solvents, and have high basicity and nucleophilicity, ether compounds having 7 or less carbon atoms in total, and other compounds that can be catalyst poisons. Therefore, it is useful as a cocatalyst for the polymerization of olefins and dienes.

[0414] The present invention includes a method for producing a polymer, which comprises polymerizing at least one monomer selected from the group consisting of olefins and dienes using the composition of the present invention as a cocatalyst.

[0415] Specifically, for example, the production of a polymer using the compound (compound (1)) (or composition) of the present invention as a cocatalyst can be carried out according to the method described in the test examples below.

[0416] Examples

[0417] Hereinafter, the present invention will be specifically described by way of examples, production examples, and test examples, but the present invention is not limited to these examples. For %, with respect to the yield, it represents mol / mol%, and for others, unless otherwise specified, it represents weight %. In addition, unless otherwise specified, room temperature represents a temperature of 15°C to 30°C.

[0418] It should be noted that the following equipment was used for analysis.

[0419] 1 H-NMR and 19 F-NMR: 400YH manufactured by JEOL Ltd.

[0420] [Example 1]

[0421] Dicetyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.92 g, 1.93 mmol) and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (manufactured by AGC Inc.) (1.00 g, 0.97 mmol) were added to dichloromethane (10 ml), and then 6M hydrochloric acid (15 ml) was added, followed by stirring at room temperature for 1 hour. After separating the reaction solution by liquid separation, the organic phase was concentrated. After adding n-hexane (15 ml) to the concentrated solution and stirring, it was concentrated. After repeating this operation, an oily bis(dicetyl ether) complex of hydrogen tetrakis(pentafluorophenyl)borate (1.67 g) was obtained.

[0422] 1 H NMR (CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 104H), 1.59 (m, 8H), 3.60 (t, 8H);

[0423] 1919F NMR (CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0424] It was confirmed that the complex (composition) obtained in Example 1 was dissolved in n-hexane at a concentration of 20% by weight.

[0425] [Example 2]

[0426] After dissolving bis(hexadecyl) ether (0.56 g, 1.21 mmol) and the ether complex of hydrogen tetrakis(pentafluorophenyl)borate (0.50 g, 0.60 mmol) obtained by a method known per se (for example, refer to Organometallics, 2000, 19, 1442 - 1444) in 1,2-dichloroethane (10 ml), it was concentrated. After repeating the operation of adding 1,2-dichloroethane (10 ml) to the concentrated solution, stirring, and then concentrating twice, the operation of adding n-hexane (10 ml) to the concentrated solution, stirring, and then concentrating was repeated three times. An oily bis(bis(hexadecyl) ether) complex of hydrogen tetrakis(pentafluorophenyl)borate (0.97 g) was obtained.

[0427] [Example 3]

[0428] After dissolving bis(tetradecyl) ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.50 g, 1.21 mmol) and the ether complex of hydrogen tetrakis(pentafluorophenyl)borate (0.50 g, 0.60 mmol) in 1,2-dichloroethane (10 ml), it was concentrated. After repeating the operation of adding 1,2-dichloroethane (10 ml) to the concentrated solution, stirring, and then concentrating twice, the operation of adding hexane (10 ml) to the concentrated solution, stirring, and then concentrating was repeated three times. An oily bis(bis(tetradecyl) ether) complex of hydrogen tetrakis(pentafluorophenyl)borate (0.94 g) was obtained.

[0429] 1 1H NMR (CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 88H), 1.65 (m, 8H), 3.79 (t, 8H);

[0430] 19 19F NMR (CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0431] It was confirmed that the complex (composition) obtained in Example 3 was dissolved in n-hexane at a concentration of 20% by weight.

[0432] [Example 4]

[0433] (1) N,N-dioctadecylaniline (3.3 g, 5.5 mmol) and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (5.0 g, 5.5 mmol), which are prepared by a method known per se (for example, refer to Huaxue Xuebao, 2008, 66(14), 1687 - 1692), are suspended in n - hexane (50 mL), and then 1.0 M hydrogen chloride - ether solution (5.5 mL) is added dropwise. Stirring is carried out at room temperature for 3 hours. The resulting suspension is filtered, and the filtrate is concentrated under reduced pressure at 50 °C to obtain N,N - dioctadecylaniline tetrakis(pentafluorophenyl)borate (7.0 g, 90%).

[0434] 1 1H NMR (CDCl3) δ: 0.86 - 0.89 (6H, m), 1.15 - 1.50 (27H, m), 3.40 - 3.50 (4H, m), 7.26 - 7.28 (2H, m), 7.58 - 7.63 (3H, m);

[0435] 19 19F NMR (CDCl3) δ: - 133.8 (8F, t), - 163.3 (4F, t), - 167.4 (8F, t).

[0436] (2) n - Hexane (474 mg) is added to N,N - dioctadecylaniline tetrakis(pentafluorophenyl)borate (127.8 mg, 0.1 mmol) obtained in the above (1), and ditetradecyl ether (21 mg, 0.05 mmol) is added to the prepared two - layer separation solution (concentration: 20 wt%). Stirring is carried out to obtain a homogeneous n - hexane solution.

[0437] [Example 5]

[0438] n - Hexane (474 mg) is added to N,N - dioctadecylaniline tetrakis(pentafluorophenyl)borate (127.8 mg, 0.1 mmol) obtained in (1) of Example 4, and didodecyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (17.7 mg, 0.05 mmol) is added to the prepared two - layer separation solution (concentration: 20 wt%). Stirring is carried out to obtain a homogeneous n - hexane solution.

[0439] [Example 6]

[0440] n - Hexane (474 mg) is added to N,N - dioctadecylaniline tetrakis(pentafluorophenyl)borate (127.8 mg, 0.1 mmol) obtained in (1) of Example 4, and dibutyl ether (manufactured by Junsei Chemical Co., Ltd.) (6.5 mg, 0.2 mmol) is added to the prepared two - layer separation solution (concentration: 20 wt%). Stirring is carried out to obtain a homogeneous n - hexane solution.

[0441] [Example 7]

[0442] Dissolve dioctadecyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.66 g, 1.21 mmol) and hydrogen tetrakis(pentafluorophenyl)borate ether complex (0.50 g, 0.60 mmol) in dichloromethane (15 ml), and then concentrate. Repeat the operation of adding dichloromethane (15 ml) to the concentrated solution, stirring, and then concentrating 4 times. After that, repeat the operation of adding n-hexane (10 ml) to the concentrated solution, stirring, and then concentrating 3 times. Obtain a solid hydrogen tetrakis(pentafluorophenyl)borate bis(dioctadecyl ether) complex (1.05 g).

[0443] 1 H NMR (CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 120H), 1.65 (m, 8H), 3.79 (t, 8H);

[0444] 19 F NMR (CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0445] Confirm that the complex (composition) obtained in Example 7 is dissolved in n-hexane at a concentration of 20% by weight.

[0446] [Example 8]

[0447] Dissolve didodecyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.45 g, 1.21 mmol) and hydrogen tetrakis(pentafluorophenyl)borate ether complex (0.50 g, 0.60 mmol) in 1,2-dichloroethane (10 ml), and then concentrate. Repeat the operation of adding 1,2-dichloroethane (10 ml) to the concentrated solution, stirring, and then concentrating 2 times. After that, repeat the operation of adding methylcyclohexane (10 ml) to the concentrated solution, stirring, and then concentrating 3 times. Obtain an oily hydrogen tetrakis(pentafluorophenyl)borate bis(didodecyl ether) complex (0.90 g).

[0448] 1 H NMR (CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 72H), 1.65 (m, 8H), 3.60 (t, 8H);

[0449] 19 F NMR (CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0450] Confirm that the complex (composition) obtained in Example 8 is dissolved in methylcyclohexane at a concentration of 20% by weight.

[0451] [Example 9]

[0452] Dissolve didodecyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.38 g, 1.21 mmol) and hydrogen tetrakis(pentafluorophenyl)borate ether complex (0.50 g, 0.60 mmol) in 1,2-dichloroethane (10 ml), and then concentrate. Repeat the operation of adding 1,2-dichloroethane (10 ml) to the concentrated solution, stirring, and then concentrating twice. After that, repeat the operation of adding methylcyclohexane (10 ml) to the concentrated solution, stirring, and then concentrating three times. Obtain an oily hydrogen tetrakis(pentafluorophenyl)borate bis(didodecyl ether) complex (0.81 g).

[0453] 1 H NMR (CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 56H), 1.65 (m, 8H), 3.60 (t, 8H);

[0454] 19 F NMR (CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0455] Confirm that the complex (composition) obtained in Example 9 is dissolved in methylcyclohexane at a concentration of 20% by weight.

[0456] [Example 10]

[0457] Add an ether solution of lithium tetrakis(heptafluoronaphthyl)borate (47 wt%, 5.00 g, 2.28 mmol) prepared by a method known per se (for example, refer to International Publication No. 2007 / 070770) to 1,2-dichloroethane (10 ml), then add 6M hydrochloric acid (7.6 ml), and stir at room temperature for 1 hour. After separating the reaction solution by liquid separation, concentrate the organic phase. Add ditetradecyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.88 g, 4.55 mmol) and 30 ml of 1,2-dichloroethane to the concentrated solution and dissolve, and then concentrate. Repeat the operation of adding 1,2-dichloroethane (30 ml) to the concentrated solution, stirring, and then concentrating twice. After that, repeat the operation of adding n-hexane (30 ml) to the concentrated solution, stirring, and then concentrating three times. Obtain an oily hydrogen tetrakis(heptafluoronaphthyl)borate bis(ditetradecyl ether) complex (4.21 g).

[0458] 11H NMR (CDCl3) δ: 0.87 (t, 12H), 1.22 (m, 88H), 1.58 (m, 8H), 3.66 (t, 8H);

[0459] 19 19F NMR (CDCl3) δ: -108.3 (m, 4F), -125.1 (m, 4F), -145.1 (m, 4F), -149.0 (m, 4F), -154.5 (m, 4F), -158.3 (m, 4F), -159.8 (m, 4F).

[0460] Confirm that the complex (composition) obtained in Example 10 is dissolved in n - hexane at a concentration of 20% by weight.

[0461] [Production Example 1]

[0462] Add dodecyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.00 g, 2.57 mmol) and cesium carbonate (1.26 g, 3.85 mmol) to 20 ml of ethanol, and react at 150 °C for 30 minutes using a microwave synthesis apparatus (manufactured by Biotage). After the reaction, add water and methylcyclohexane, separate the layers, and concentrate the organic phase. Purify the concentrated solution by column chromatography to obtain dodecylethyl ether (0.60 g) in the form of a white solid.

[0463] 1 1H NMR (CDCl3) δ: 0.89 (t, 3H), 1.21 (t, 3H), 1.26 (m, 38H), 1.57 (m, 2H), 3.41 (t, 2H), 3.47 (q, 2H).

[0464] [Example 11]

[0465] Dissolve the dodecylethyl ether (0.21 g, 0.60 mmol) obtained in Production Example 1 and hydrogen tetrakis(pentafluorophenyl)borate ether complex (0.25 g, 0.30 mmol) in 1,2 - dichloroethane (5 ml), and then concentrate. Repeat the operation of adding 1,2 - dichloroethane (5 ml) to the concentrated solution, stirring, and then concentrating twice. Then repeat the operation of adding methylcyclohexane (5 ml) to the concentrated solution, stirring, and then concentrating three times. Obtain the solid hydrogen tetrakis(pentafluorophenyl)borate bis(dodecylethyl ether) complex (0.46 g).

[0466] 1 1H NMR (CDCl3) δ: 0.87 (m, 12H), 1.27 (m, 82H), 1.65 (m, 4H), 3.76 (t, 4H), 3.85 (q, 4H);

[0467] 19 19F NMR (CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0468] It was confirmed that the complex (composition) obtained in Example 11 was dissolved in methylcyclohexane at a concentration of 20% by weight.

[0469] [Production Example 2]

[0470] Tetradecyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.79 g, 6.44 mmol), ethylene glycol (0.20 g, 3.22 mmol), tetrabutylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.10 g, 0.32 mmol), and potassium hydroxide (0.64 g, 9.67 mmol) were added to dioxane (10 ml), and the mixture was heated at 100 °C for 3 hours. After cooling, water and diethyl ether were added for liquid separation. The organic phase was dried over sodium sulfate and then concentrated. The concentrate was purified by column chromatography to obtain ethylene glycol ditetradecyl ether (0.32 g) as a white solid.

[0471] 1 1H NMR (CDCl3) δ: 0.88 (t, 6H), 1.25 (m, 44H), 1.58 (m, 4H), 3.46 (t, 4H), 3.57 (s, 4H).

[0472] [Example 12]

[0473] Ethylene glycol ditetradecyl ether (0.22 g, 0.48 mmol) and ethyl ether complex of tetrakis(pentafluorophenyl)borate hydride (0.20 g, 0.24 mmol) obtained in Production Example 2 were dissolved in 1,2-dichloroethane (5 ml) and then concentrated. The operation of adding 1,2-dichloroethane (5 ml) to the concentrate, stirring, and then concentrating was repeated 2 times. Then, the operation of adding n-hexane (5 ml) to the concentrate, stirring, and then concentrating was repeated 3 times. An oily complex of tetrakis(pentafluorophenyl)borate hydride bis(ethylene glycol ditetradecyl ether) (0.41 g) was obtained.

[0474] 1 1H NMR (CDCl3) δ: 0.87 (t, 12H), 1.27 (m, 88H), 1.58 (m, 8H), 3.58 (t, 8H), 3.70 (s, 8H);

[0475] 19 19F NMR (CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0476] Confirm that the complex (composition) obtained in Example 12 is dissolved in n-hexane at a concentration of 20% by weight.

[0477] [Production Example 3]

[0478] Dissolve N,N-dioctadecylamine (2.0 g, 3.8 mmol) and triethylamine (0.5 g, 5.0 mmol) in tetrahydrofuran (10 mL). Add trifluoroacetic anhydride (1.0 g, 4.8 mmol) thereto at room temperature. Stir at room temperature for 1 hour, add water, and extract with ethyl acetate. Wash the organic layer with 1M hydrochloric acid and saturated brine, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by column chromatography (n-hexane / ethyl acetate = 100 / 0 - 95 / 5) to obtain N,N-dioctadecyl-2,2,2-trifluoroacetamide (1.87 g, 79%).

[0479] 1 1H NMR (CDCl3) δ: 0.89 (6H, t), 1.26 - 1.43 (62H, m), 1.56 - 1.59 (4H, m), 3.30 - 3.37 (4H, m);

[0480] 19 19F NMR (CDCl3) δ: -68.1 (3F, s).

[0481] [Production Example 4]

[0482] Dissolve the N,N-dioctadecyl-2,2,2-trifluoroacetamide (1.0 g, 1.6 mmol) obtained in Production Example 3 in tetrahydrofuran (10 mL), add 1M borane-tetrahydrofuran complex tetrahydrofuran solution (5 mL), and reflux for 3 hours. After cooling the mixture in ice, carefully add water dropwise and extract with ethyl acetate. Wash the organic layer with saturated brine, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain N,N-dioctadecyl-2,2,2-trifluoroethylamine (0.87 g, 88%).

[0483] 1 1H NMR (CDCl3) δ: 0.88 (6H, t), 1.25 - 1.40 (60H, m), 1.42 - 1.44 (4H, m), 2.56 (4H, t), 3.00 (2H, q);

[0484] 19 19F NMR (CDCl3) δ: -69.2 (3F, t).

[0485] [Production Example 5]

[0486] Dissolve N,N-dioctadecyl-2,2,2-trifluoroethylamine (1.0 g, 1.7 mmol) obtained in Production Example 4 in n-hexane (10 mL), add 1.0 M hydrogen chloride-ether solution (10 mL), and stir at room temperature for 3 hours. Filter the precipitated precipitate, wash it with n-hexane, and dry it under reduced pressure to obtain N,N-dioctadecyl-2,2,2-trifluoroethylamine hydrochloride (0.987 g, 93%).

[0487] 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19 - 1.40 (60H, m), 1.93 (4H, br s), 3.15 (4H, br s), 3.77 (2H, q);

[0488] 19 F NMR (CDCl3) δ: -61.4 (3F, t).

[0489] [Production Example 6]

[0490] N,N-dioctadecyl-2,2,2-trifluoroethylamine obtained in Production Example 5

[0491] Dissolve the hydrochloride (0.32 g, 0.50 mmol) in chloroform (30 mL), add lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (0.45 g, 0.5 mmol), and stir at room temperature for 1 hour. Remove the insoluble matter by filtration and concentrate the filtrate under reduced pressure. Dry the residue under reduced pressure at 45 °C to obtain N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (0.62 g, 97%).

[0492] 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19 - 1.40 (60H, m), 1.94 (4H, br s), 3.15 (4H, br s), 3.77 (2H, q);

[0493] 19 F NMR (CDCl3) δ: -64.7 (3F, t), -132.1 (8H, m), -161.1 (4H, m), -165.5 (8H, m).

[0494] [Example 13]

[0495] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (0.30 g, 0.22 mmol) obtained in Production Example 6 and ditetradecyl ether (0.09 g, 0.22 mmol) were mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and ditetradecyl ether.

[0496] 1 H NMR (CDCl3) δ: 0.85 - 0.90 (12H, m), 1.20 - 1.33 (104H, m), 1.52 - 1.68 (8H, m), 3.14 - 3.18 (4H, m), 3.40 (4H, t), 3.62 (2H, q);

[0497] 19 F NMR (CDCl3) δ: -66.8 (3F, br s), -134.0 (8F, m), -163.2 (4F, t), -167.5 (8F, m).

[0498] n-Hexane was added to the composition obtained in Example 13 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0499] Isohexane was added to the composition obtained in Example 13 to prepare a 20 wt% isohexane solution, which was confirmed to be a homogeneous solution.

[0500] n-Heptane was added to the composition obtained in Example 13 to prepare a 20 wt% n-heptane solution, which was confirmed to be a homogeneous solution.

[0501] ISOPAR E was added to the composition obtained in Example 13 (R) to prepare a 20 wt% ISOPAR E (R) solution, which was confirmed to be a homogeneous solution.

[0502] Cyclohexane was added to the composition obtained in Example 13 to prepare a 20 wt% cyclohexane solution, which was confirmed to be a homogeneous solution.

[0503] Methylcyclohexane was added to the composition obtained in Example 13 to prepare a 20 wt% methylcyclohexane solution, which was confirmed to be a homogeneous solution.

[0504] [Example 14]

[0505] N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (300 mg, 0.23 mmol) obtained in Production Example 6 and dibutyl ether (62 mg, 0.46 mmol) were mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dibutyl ether.

[0506] 1 1H NMR (CDCl3) δ: 0.87 (6H, t), 0.92 (12H, t), 1.20 - 1.68 (78H, m), 3.14 - 3.18 (4H, m), 3.41 (8H, t), 3.62 (2H, q);

[0507] 19 19F NMR (CDCl3) δ: -66.7 (3F, s), -134.0 (8F, s), -163.3 (4F, t), -167.5 (8H, m).

[0508] It was confirmed that the composition obtained in Confirmation Example 14 was dissolved in n-hexane at a concentration of 30% by weight.

[0509] [Example 15]

[0510] N,N-ditetradecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (58 mg, 0.05 mmol) and didodecyl ether (40 mg, 0.10 mmol) were added and mixed to obtain a composition containing N,N-ditetradecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and didodecyl ether.

[0511] 1 1H NMR (CDCl3) δ: 0.85 - 0.88 (18H, m), 1.24 - 1.35 (116H, m), 1.51 - 1.58 (8H, m), 1.64 - 1.70 (4H, m), 3.11 - 3.15 (4H, m), 3.38 (8H, t), 3.60 (2H, q);

[0512] 19 19F NMR (CDCl3) δ: -66.6 (3F, s), -134.0 (8F, s), -163.5 (4F, t), -167.6 (8F, t).

[0513] n-Hexane was added to the composition obtained in Example 15 to prepare a 20% by weight n-hexane solution, which was confirmed to be a homogeneous solution.

[0514] [Example 16]

[0515] N,N-Dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (60 mg, 0.05 mmol) and dihexadecyl ether (23 mg, 0.05 mmol) were added and mixed to obtain a composition containing N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dihexadecyl ether.

[0516] 1 H NMR (CDCl3) δ: 0.86 - 0.90 (12H, m), 1.20 - 1.36 (104H, m), 1.52 - 1.58 (4H, m), 1.63 - 1.70 (4H, m), 3.15 - 3.19 (4H, m), 3.39 (4H, t), 3.64 (2H, q);

[0517] 19 F NMR (CDCl3) δ: -66.7 (3F, s), -134.1 (8F, s), -163.5 (4F, t), -167.6 (8F, t).

[0518] n-Hexane was added to the composition obtained in Example 16 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0519] [Example 17]

[0520] N,N-Dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) and dioctyl ether (12 mg, 0.05 mmol) obtained in Production Example 6 were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dioctyl ether.

[0521] 1 H NMR (CDCl3) δ: 0.88 (12H, t), 1.20 - 1.37 (80H, m), 1.52 - 1.58 (4H, m), 1.65 - 1.70 (4H, m), 3.14 - 3.19 (4H, m), 3.39 (4H, t), 3.63 (2H, q);

[0522] 19 F NMR (CDCl3) δ: -66.6 (3F, br s), -134.0 (8F, br s), -163.4 (4F, t), -167.6 (8F, t).

[0523] n-Hexane was added to the composition obtained in Example 17 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0524] [Example 18]

[0525] N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) and didodecyl ether (15 mg, 0.05 mmol) obtained in Production Example 6 were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and didodecyl ether.

[0526] 1 H NMR (CDCl3) δ: 0.86 - 0.90 (12H, m), 1.20 - 1.38 (96H, m), 1.53 - 1.60 (4H, m), 1.65 - 1.72 (4H, m), 3.15 - 3.20 (4H, m), 3.39 (4H, t), 3.65 (2H, q);

[0527] 19 F NMR (CDCl3) δ: -66.4 (3F, br s), -134.0 (8F, br s), -163.4 (4F, t), -167.5 (8F, m).

[0528] n-Hexane was added to the composition obtained in Example 18 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0529] [Example 19]

[0530] N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) and dihexadecyl ether (23 mg, 0.05 mmol) obtained in Production Example 6 were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dihexadecyl ether.

[0531] 1 H NMR (CDCl3) δ: 0.86 - 0.98, (12H, m), 1.20 - 1.35 (112H, m), 1.52 - 1.75 (8H, m), 3.15 - 3.20 (4H, m), 3.39 (4H, t), 3.65 (2H, q);

[0532] 19 F NMR (CDCl3) δ: -66.5 (3F, br s), -134.2 (8F, br s), -163.6 (4F, t), -167.7 (8F, m).

[0533] n-Hexane was added to the composition obtained in Example 19 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0534] [Example 20]

[0535] N,N-Dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) and diphenyl ether (8.5 mg, 0.05 mmol) obtained in Production Example 6 were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and diphenyl ether.

[0536] 1 1H NMR (CDCl3) δ: 0.86 - 0.90, (6H, m), 1.20 - 1.40 (58H, m), 1.62 - 1.68 (4H, m), 3.12 - 3.16 (4H, m), 3.61 (4H, q), 6.99 - 7.03 (4H, m), 7.08 - 7.12 (2H, m), 7.31 - 7.36 (4H, m);

[0537] 19 19F NMR (CDCl3) δ: -66.9 (3F, br s), -134.1 (8F, br s), -163.4 (4F, t), -167.6 (8F, m).

[0538] n-Hexane was added to the composition obtained in Example 20 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0539] [Example 21]

[0540] N,N-Dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) and octadecyl phenyl ether (18 mg, 0.05 mmol) obtained in Production Example 6 were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and octadecyl phenyl ether.

[0541] 1 1H NMR (CDCl3) δ: 0.84 - 0.98 (12H, m), 1.20 - 1.44 (85H, m), 1.62 - 1.81 (6H, m), 3.13 - 3.18 (4H, m), 3.61 (4H, q), 3.95 (2H, t), 6.88 - 6.94 (2H, m), 7.25 - 7.30 (3H, m);

[0542] 1919F NMR (CDCl3) δ: -66.8 (3F, br s), -134.1 (8F, br s), -163.4 (4F, t), -167.6 (8F, m).

[0543] n-Hexane was added to the composition obtained in Example 21 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0544] [Example 22]

[0545] N,N-Dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) and cyclopentyl methyl ether (10 mg, 0.10 mmol) obtained in Production Example 6 were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and cyclopentyl methyl ether.

[0546] 1 1H NMR (CDCl3) δ: 0.88 (6H, t), 1.20 - 1.35 (60H, m), 1.53 - 1.56 (4H, m), 1.61 - 1.76 (16H, m), 3.12 - 3.17 (4H, m), 3.28 (6H, s), 3.61 (2H, q), 3.79 - 3.83 (2H, m);

[0547] 19 19F NMR (CDCl3) δ: -66.6 (3F, br s), -133.9 (8F, br s), -163.5 (4F, t), -167.6 (8F, m).

[0548] n-Hexane was added to the composition obtained in Example 22 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0549] [Production Example 7]

[0550] Synthesis of N,N-Ditetradecyl-2,2,2-trifluoroethylamine

[0551] 1 - tetradecanal (4.0 g, 18.8 mmol), 2,2,2 - trifluoroethylamine (0.90 g, 9.1 mmol) and acetic acid (0.3 mL) were dissolved in tetrahydrofuran (30 mL). Sodium triacetoxyborohydride (4.0 g, 18.9 mmol) was added, and the mixture was stirred at room temperature for 15 h. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture to make it alkaline, and the mixture was extracted with n - hexane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n - hexane / ethyl acetate = 100 / 0 - 95 / 5) to give the title compound (4.0 g, 89%).

[0552] 1 1H NMR (CDCl3) δ: 0.88 (6H, t), 1.26 - 1.43 (48H, m), 2.55 (4H, t), 3.00 (2H, q);

[0553] 19 19F NMR (CDCl3) δ: - 71.3 (3F, t).

[0554] [Production Example 8]

[0555] Synthesis of N,N - ditetradecyl - 2,2,2 - trifluoroethylamine hydrochloride

[0556] N,N - ditetradecyl - 2,2,2 - trifluoroethylamine (1.50 g, 3.05 mmol) obtained in Production Example 7 was dissolved in n - hexane (30 mL). 1.0 M hydrogen chloride - ether solution (20 mL) was added, and the mixture was stirred for 1 h. The reaction mixture was concentrated under reduced pressure to give the title compound (1.45 g, 90%).

[0557] 1 1H NMR (CDCl3) δ: 0.88 (6H, t), 1.20 - 1.40 (44H, m), 1.96 (4H, br s), 3.15 (4H, br s), 3.78 (2H, q);

[0558] 19 19F NMR (CDCl3) δ: - 63.4 (3F, t).

[0559] [Production Example 9] Synthesis of N,N - ditetradecyl - 2,2,2 - trifluoroethylammonium tetrakis(pentafluorophenyl)borate

[0560] Dissolve N,N-ditetradecyl-2,2,2-trifluoroethylamine hydrochloride (0.60 g, 1.14 mmol) obtained in Production Example 8 in chloroform (30 mL), add lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (1.04 g, 1.14 mmol), and stir at room temperature for 1 hour. Remove the insoluble matter by filtration, and concentrate the filtrate under reduced pressure. Dry the residue under reduced pressure at 70 °C to obtain the title compound (1.34 g, 100%).

[0561] 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19 - 1.36 (44H, m), 1.65 - 1.70 (4H, m), 3.14 - 3.18 (4H, m), 3.62 (2H, q);

[0562] 19 F NMR (CDCl3) δ: -66.4 (3F, t), -134.0 (8F, m), -163.4 (4F, t), -167.6 (8F, t).

[0563] [Production Example 10]

[0564] Synthesis of N,N-dicetyl-2,2,2-trifluoroethylamine

[0565] Dissolve 1-hexadecanal (4.0 g, 16.6 mmol), 2,2,2-trifluoroethylamine (0.84 g, 8.5 mmol) and acetic acid (0.5 mL) in tetrahydrofuran (50 mL), add sodium triacetoxyborohydride (4.0 g, 18.9 mmol), and stir at room temperature for 15 hours. Add saturated aqueous sodium hydrogen carbonate solution to the reaction mixture to make it alkaline, and extract with n-hexane. Wash the organic layer with saturated brine, dry with anhydrous sodium sulfate, and concentrate under reduced pressure. Purify the residue by silica gel column chromatography (n-hexane / ethyl acetate = 100 / 0 - 95 / 5) to obtain the title compound (4.56 g, 98%).

[0566] 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.26 - 1.43 (56H, m), 2.56 (4H, t), 3.00 (2H, q);

[0567] 19 F NMR (CDCl3) δ: -71.3 (3F, t).

[0568] [Production Example 11]

[0569] Synthesis of N,N-dicetyl-2,2,2-trifluoroethylamine hydrochloride

[0570] Dissolve N,N-dihexadecyl-2,2,2-trifluoroethylamine (1.50 g, 2.74 mmol) obtained in Production Example 10 in n-hexane (30 mL), add 1.0 M hydrogen chloride-ether solution (20 mL), and stir for 1 hour. Concentrate the reaction mixture under reduced pressure to obtain the title compound (1.55 g, 97%).

[0571] 1 1H NMR (CDCl3) δ: 0.88 (6H, t), 1.19 - 1.40 (52H, m), 1.93 (4H, br s), 3.15 (4H, br s), 3.77 (2H, q);

[0572] 19 19F NMR (CDCl3) δ: -63.4 (3F, t).

[0573] [Production Example 12]

[0574] Synthesis of N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate

[0575] Dissolve N,N-dihexadecyl-2,2,2-trifluoroethylamine hydrochloride (0.60 g, 1.03 mmol) obtained in Production Example 11 in chloroform (30 mL), add lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (0.95 g, 1.05 mmol), and stir at room temperature for 1 hour. Remove the insoluble matter by filtration and concentrate the filtrate under reduced pressure. Dry the residue under reduced pressure at 70 °C to obtain the title compound (1.51 g).

[0576] 1 1H NMR (CDCl3) δ: 0.88 (6H, t), 1.19 - 1.36 (54H, m), 1.65 - 1.70 (4H, m), 3.14 - 3.18 (4H, m), 3.62 (2H, q);

[0577] 19 19F NMR (CDCl3) δ: -66.4 (3F, t), -134.0 (8F, m), -163.4 (4F, t), -167.6 (8F, t).

[0578] [Example 23]

[0579] Dissolve N,N-dihexadecyl-2,2,2-trifluoroethylamine hydrochloride (8.10 g, 13.9 mmol) obtained in Production Example 11 in dichloromethane (80 mL), add ditetradecyl ether (8.10 g, 13.9 mmol) and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (14.2 g, 13.7 mmol), and stir at room temperature for 1 hour. Add water to the reaction mixture and stir at room temperature for 1 hour. Separate the aqueous layer and wash the organic layer with water. Dry the organic layer over anhydrous sodium sulfate, then filter, and concentrate the filtrate under reduced pressure. Dry the residue under reduced pressure at 80 °C to obtain a composition (22.5 g) containing N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and ditetradecyl ether.

[0580] 1 H NMR (CDCl3) δ: 0.87 - 0.89 (12H, m), 1.20 - 1.80 (104H, m), 3.21 - 3.24 (4H, m), 3.38 - 3.41 (4H, m), 3.69 (2H, q);

[0581] 19 F NMR (CDCl3) δ: -66.7 (3F, brs), -134.0 (8F, m), -163.4 (4F, t), -167.5 (8F, t).

[0582] Add n-hexane to the composition obtained in Example 23 to prepare a 20 wt% n-hexane solution, and confirm that it is a homogeneous solution.

[0583] [Example 24]

[0584] Mix N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (439.2 mg, 0.36 mmol) and didodecyl ether (254 mg, 0.72 mmol) obtained in Production Example 12, and add n-hexane (1.756 g) to prepare a homogeneous n-hexane solution of a composition containing N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and didodecyl ether. Confirm that the solution is a homogeneous solution. Concentrate the solution under reduced pressure and perform NMR analysis.

[0585] 1 H NMR (CDCl3) δ: 0.87 - 0.91 (12H, m), 1.20 - 1.42 (100H, m), 1.53 - 1.69 (12H, m), 3.20 - 3.24 (4H, m), 3.40 (8H, t), 3.67 (2H, q);

[0586] 19 19F NMR (CDCl3) δ: -66.9 (3F, t), -134.0 (8F, m), -163.8 (4F, t), -167.4 (8F, t).

[0587] [Example 25]

[0588] Suspend ditetradecyl ether (5.96 g, 14.3 mmol) and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (5.00 g, 4.81 mmol) in dichloroethane (25 mL), add 6M hydrochloric acid (5.5 mL, 30.0 mmol), and stir at room temperature for 2 hours. Obtain the organic layer and wash it with water (10 mL). After drying the organic layer with anhydrous sodium sulfate, concentrate it under reduced pressure. Dry it under reduced pressure at room temperature for 16 hours to obtain a composition (10.4 g) containing bis(ditetradecyl ether) complex of hydrogen tetrakis(pentafluorophenyl)borate and ditetradecyl ether.

[0589] 1 1H NMR (CDCl3) δ: 0.88 (18H, t), 1.20 - 1.30 (94H, m), 1.56 - 1.60 (12H, m), 3.57 (12H, t);

[0590] 19 19F NMR (CDCl3) δ: -134.0 (8F, m), -163.8 (4F, t), -167.8 (8F, t).

[0591] Add n-hexane to the composition obtained in Example 25 to prepare a 20 wt% n-hexane solution, which was confirmed to be a homogeneous solution.

[0592] [Comparative Example 1]

[0593] It was confirmed that the ethyl ether complex of hydrogen tetrakis(pentafluorophenyl)borate obtained by a method known per se (for example, refer to Organometallics, 2000, 19, 1442 - 1444) is poorly soluble in aliphatic hydrocarbon solvents such as hexane and cyclohexane. In the test examples described later, the ethyl ether complex of hydrogen tetrakis(pentafluorophenyl)borate was used as the cocatalyst for Comparative Example 1.

[0594] [Comparative Example 2]

[0595] An attempt was made to prepare a 10 wt% n-hexane solution of N,N-dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate obtained by a method known per se (for example, refer to the specification of US Patent No. 6121185), but a homogeneous solution was not obtained. In the test examples described later, N,N-dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate was used as the cocatalyst for Comparative Example 2.

[0596] [Test Example] (Polymerization Performance Evaluation)

[0597] The following shows a general polymerization method using the composition (complex) of the present invention as a cocatalyst.

[0598] In a glove box, 1-octene, triisobutylaluminum (TIBA, 0.55 M n-hexane solution), and a solvent (methylcyclohexane (MCH) or toluene) were added to a 100 mL autoclave to prepare a comonomer solution. A polymerization catalyst, dimethylsilylene (tert-butylamide)-(tetramethylcyclopentadienyl)-titanium(IV)-dichloride (CGC), triisobutylaluminum (0.55 M n-hexane solution), and a solvent were added to prepare a catalyst solution with a predetermined concentration, which was then transferred to a Schlenk tube. The composition (cocatalyst) of the present invention was dissolved in a solvent to prepare a cocatalyst solution with a predetermined concentration, which was then transferred to a Schlenk tube. The comonomer solution, catalyst solution, and cocatalyst solution were mixed in such a way that the total amount of the solvent and the total amount of triisobutylaluminum were constant. After purging the autoclave with ethylene gas, the catalyst solution and the cocatalyst solution were sequentially added to the autoclave, and immediately the ethylene gas pressure was adjusted to a predetermined pressure, and stirring was carried out at a predetermined temperature (25 °C or 100 °C) for a predetermined time. After cooling the reaction mixture to ice-cold, the ethylene gas was discharged, and then the mixture was injected into methanol (100 mL) containing 3 mL of hydrochloric acid and stirred at room temperature for 30 minutes. The precipitate was filtered and dried under reduced pressure at 60 °C to obtain an ethylene-octene copolymer.

[0599] Melting Point Measurement

[0600] Measurement based on differential scanning calorimetry (DSC) was carried out using a DSC6220 device (Seiko Instruments Inc.). The sample (polymer) was heated from 40 °C to 150 °C at a rate of 10 °C / minute to measure the melting point.

[0601] Hereinafter, the results of the polymerization reactions at 25 °C or 100 °C are shown in Table 1 and Table 2, respectively.

[0602] [Table 1]

[0603]

[0604] Reaction conditions; catalyst: CGC, catalyst:cocatalyst = 1:1, TIBA (total amount 3000 μmol),

[0605] Total amount of solvent (40 mL), 1-octene (1 mL), ethylene pressure (8 atm), 25 °C

[0606] [Table 2]

[0607]

[0608] Reaction conditions; catalyst: CGC, catalyst: cocatalyst = 1:1, TIBA (total 100 μmol),

[0609] Total amount of solvent (40 mL), 1-octene (1 mL), ethylene pressure (8 atmospheres), 100 °C

[0610] According to Table 1 and Table 2, for the compositions (or complexes) of the present invention (Examples 2, 3, 5, 10, and 13), in the polymerization reaction in methylcyclohexane (MCH), the activity is higher than that of the compound of Comparative Example 2 regardless of the polymerization temperature. In addition, in the polymerization reaction in toluene, the activity of the compositions (or complexes) of the present invention (Examples 3 and 10) is also higher than that of the compound of Comparative Example 1 (Table 1). Furthermore, as shown in Table 1, the compositions (or complexes) of the present invention (Examples 2, 3, 5, 10, and 13) give polymers with a melting point lower than that of the comparative examples according to the polymerization conditions, and it is considered that the incorporation amount of the comonomer increases.

[0611] Industrial applicability

[0612] The composition of the present invention is soluble (or readily soluble) in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, and does not become a catalyst poison, and thus is useful as a cocatalyst for the polymerization of olefins and dienes.

[0613] This application is based on Japanese Patent Application Nos. 2020-043244 filed on March 12, 2020, 2020-144176 filed on August 28, 2020, and 2020-196703 filed on November 27, 2020, and the contents of all of them are incorporated herein by reference.

Claims

1. A composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (4), wherein, R 1 、R 2 、R 3 and R 4 each independently represents an aryl group substituted by one or more fluorine atoms or one or more fluorinated C 1-4 alkyl groups 6-14 aryl group. A + represents a hydrogen ion, a cation having 25 or more carbon atoms in total represented by the formula (2), or a cation having 25 or more carbon atoms in total represented by the formula (3). In formula (2), R 5 , R 6 and R 7 each independently represents an optionally substituted C 1-30 alkyl or an optionally substituted C 6-14 aryl, In formula (3), Ar 1 , Ar 2 and Ar 3 each independently represents an optionally C 1-30 alkyl or C 1-30 alkoxy-substituted C 6-14 aryl, and R and R' each independently represent optionally substituted C 1-30 alkyl, optionally substituted C 3-15 cycloalkyl or optionally substituted C 6-14 aryl, Among them, A + When it is a hydrogen ion, the total carbon number of R and R' is 20 or more, and the content of the compound represented by the formula (4) is 2 moles or more with respect to 1 mole of the compound represented by the formula (1). A + When it is the cation represented by the formula (2) or the cation represented by the formula (3), the total carbon number of R and R' is 8 or more; Optionally substituted means unsubstituted or having one or more substituents selected from at least one of the following groups: (1) a halogen atom, (4) C 1-30 alkyl, (5) halo C 1-30 alkyl, (6) C 3-8 cycloalkyl, (7) C 1-30 alkoxy, (8) halo C 1-30 alkoxy, (9) C 6-14 aryl.

2. The composition according to claim 1, wherein R and R' are each independently C 1-30 alkyl or optionally substituted C 6-14 aryl, and The total carbon number of R and R' is 25 or more when A + is a hydrogen ion, and is 8 or more when A + is the cation represented by the formula (2) or the cation represented by the formula (3).

3. The composition according to claim 1 or 2, wherein, R 1 、R 2 、R 3 and R 4 each independently represents the following groups substituted by one or more fluorine atoms or trifluoromethyl groups respectively: phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 1-anthryl, 2-anthryl, 9-anthryl, 9-phenanthryl or 3-phenanthryl.

4. The composition according to claim 1 or 2, wherein, R 1 、R 2 、R 3 and R 4 are all pentafluorophenyl, 2,2’,3,3’,4’,5,5’,6,6’-nonafluoro-4-(1,1’-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl.

5. The composition according to claim 1 or 2, wherein A + is a hydrogen ion.

6. The composition according to claim 1 or 2, wherein A + is a cation having 35 or more carbon atoms in total represented by the formula (2), and R 5 、R 6 and R 7 each independently is C 1-30 alkyl, or C 6-14 aryl optionally substituted with substituents selected from the group consisting of the following groups: (1) a halogen atom, (2)C 1-30 alkyl, (3)C 1-30 alkoxy, and (4) Halo C 1-30 alkyl group.

7. The composition according to claim 1 or 2, wherein A + is a cation with a total carbon number of 35 or more represented by the formula (2). R 5 Optionally substituted with a substituent selected from the group consisting of the following groups C 6-14 Aryl: (1) a halogen atom, (2)C 1-30 alkyl, (3)C 1-30 alkoxy, and (4) Halogenated C 1-6 alkyl And, R 6 and R 7 each independently is an optionally substituted C 1-30 alkyl group.

8. The composition according to claim 1 or 2, wherein, A + is a cation with 35 or more carbon atoms in total as shown in the formula (2). R 5 is substituted by C 6-14 aryl-substituted C 1-30 alkyl, or C 1-30 alkyl substituted by one or more fluorine atoms, said C 6-14 aryl is substituted by one or more fluorine atoms, and R 6 and R 7 each independently is C optionally substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl: (1) Optionally, a C substituted by a halogen atom 6-14 aryl, (2) a halogen atom, and (3)C 1-30 Alkoxy group.

9. The composition according to claim 1 or 2, wherein A + is a cation having 35 or more carbon atoms in total represented by the formula (2). R 5 is a fluoro C 1-6 alkyl, and R 6 and R 7 each independently is optionally substituted with a substituent selected from the group consisting of the following groups of C 1-30 alkyl groups: (1) Optionally, a C substituted by a halogen atom 6-14 aryl, (2) a halogen atom, and (3)C 1-30 Alkoxy group.

10. The composition according to claim 1 or 2, wherein A + is a cation having 35 or more carbon atoms in total represented by the formula (3), and Ar 1 、 Ar 2 and Ar 3 each independently is phenyl optionally substituted with C 1-30 alkyl or C 1-30 alkoxy.

11. The composition according to claim 1 or 2, wherein A + is a hydrogen ion, and each of R and R' independently is: Optionally, the C is substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl groups: (1) a halogen atom, (2)C 1-30 alkoxy, and (3) Halo C 1-30 alkoxy group; Optionally substituted with a substituent selected from the group consisting of the following groups C 3-15 Cycloalkyl: (1) a halogen atom, (2)C 1-30 alkyl, (3)C 1-30 alkoxy group (4) Halogenated C 1-30 alkyl, and (5) Halo C 1-30 alkoxy group; or optionally C substituted with a substituent selected from the group consisting of the following groups 6-14 aryl: (1) a halogen atom, (2)C 1-30 alkyl, (3)C 1-30 alkoxy (4) Halo C 1-30 alkyl, and (5) Halo C 1-30 alkoxy group.

12. The composition according to claim 1 or 2, wherein A + is a hydrogen ion, and each of R and R' is independently a C 1-30 alkyl group.

13. The composition according to claim 1 or 2, wherein A + is a hydrogen ion, R and R' are each independently C 14-30 alkyl, and the total carbon number of R and R' is 28 or more.

14. The composition according to claim 1 or 2, wherein A + is a hydrogen ion, and R and R' are the same group.

15. The composition according to claim 1 or 2, wherein A + is the cation represented by the formula (2) or formula (3), R and R' are each independently C 1-30 alkyl group, and the total number of carbon atoms of R and R' is 8 or more.

16. The composition according to claim 1 or 2, wherein The content of the compound represented by the formula (4) is in the range of 0.01 to 10 moles relative to 1 mole of the compound represented by the formula (1), and A in the formula (1) + is the cation represented by the formula (2) or the formula (3).

17. The composition according to claim 1 or 2, wherein The content of the compound represented by the formula (4) is in the range of 0.01 to 3 moles relative to 1 mole of the compound represented by the formula (1), and A in the formula (1) + is the cation represented by the formula (2) or the formula (3).

18. The composition according to claim 1 or 2, having a solubility of 5% by weight or more at 25 °C in n - hexane, iso - hexane, n - heptane, n - octane, cyclohexane, methylcyclohexane, or a mixed solvent thereof.

19. The composition according to claim 1 or 2, which substantially does not contain ethers having a total carbon number of 7 or less. Substantially not containing ethers having a total carbon number of 7 or less means that 1 as a result of 1H-NMR analysis, no ether compound having a total carbon number of 7 or less is detected.

20. A cocatalyst for use in the polymerization of at least one monomer selected from the group consisting of olefins and dienes, the cocatalyst comprising the composition according to any one of claims 1 to 19.

21. A method for manufacturing a polymer, comprising: Using the composition according to any one of claims 1 to 19 as a cocatalyst to polymerize at least one monomer selected from the group consisting of olefins and dienes.

22. A manufacturing method, characterized in that, It is a method for manufacturing the following composition, the composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (4), wherein, R 1 、R 2 、R 3 and R 4 each independently represents an aryl group substituted with one or more fluorine atoms or one or more fluorinated C 1-4 alkyl groups 6-14 aryl group, A + represents a hydrogen ion, R and R' each independently represent an optionally substituted C 1-30 alkyl group, an optionally substituted C 3-15 cycloalkyl group or an optionally substituted C 6-14 aryl group, and the total number of carbon atoms of R and R' is 20 or more, and relative to 1 mole of the compound represented by the formula (1), the content of the compound represented by the formula (4) is 2 moles or more, the manufacturing method includes a step of reacting a compound represented by the following formula (5) with a compound represented by the following formula (4), in formula (5), R 1 、R 2 、R 3 and R 4 represent the same meaning as described above, R 8 and R 9 each independently represents C 1-6 alkyl, and R 8 OR 9 The total carbon number is 7 or less, R and R' in formula (4) represent the same meanings as described above; Optionally substituted means unsubstituted or having one or more substituents selected from at least one of the following groups: (1) a halogen atom, (4) C 1-30 alkyl, (5) halo C 1-30 alkyl, (6) C 3-8 cycloalkyl, (7) C 1-30 alkoxy, (8) halo C 1-30 alkoxy, (9) C 6-14 aryl.

23. The manufacturing method according to claim 22, wherein, R 8 and R 9 are both ethyl groups.

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