Group 13 element-containing compound

Abstract

To provide a novel Group 13 element-containing compound, the compound being useful as a cocatalyst for an olefin polymerization catalyst and achieving excellent performance in activating a transition metal complex as a main catalyst.SOLUTION: There is provided a Group 13 element-containing compound (A) represented by the following formula (A). [α]γ+{β}γ- (A) [In the formula, γ is an integer of 1 to 5. [α]γ+ is a cation represented by [(R1)3NH]+, [(R2)3C]+, or [(R3)3 N-R4-N(R3)3]γ+ (R1 to R4 are hydrocarbon groups or the like). {β}γ- represents one or more anions, and at least one of the anions is an anion represented by the formula [MQ4]- (M is an atom of a Group 13 element, and each of the four Q is, independently, an aryl group represented by the following formula (Q-1a) or (Q-1b)).] [In the formula, * indicates a bond to M, and Xm is a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to Group 13 element-containing compounds. [Background technology]

[0002] In olefin polymerization, borate compounds are widely used as co-catalysts to activate the transition metal complexes that serve as the main catalysts. These borate compounds are ionic compounds consisting of cation-anion ion pairs, and the Lewis acid sites or Bronsted acid sites of the cations contribute to the activation of the transition metal complexes.

[0003] As the cation, tertiary ammonium ions having one hydrogen atom on the nitrogen atom and three substituents selected from alkyl (aliphatic) groups and aryl (aromatic) groups, tertiary carbonium cations having three substituents selected from alkyl groups and aryl groups on the carbon atoms, and polyvalent cations containing these cations are widely used. For example, many technologies have been reported, such as borate compounds of tertiary ammonium ions having aryl groups as substituents on the nitrogen atoms because of their excellent olefin polymerization activity, borate compounds of tertiary trialkylammonium ions having no aryl groups as substituents on the nitrogen atoms because of their excellent affinity with aliphatic hydrocarbon solvents, and borate compounds of polyvalent cations having multiple tertiary ammonium ions in which multiple nitrogen atoms are bridged by hydrocarbon groups (e.g., Patent Documents 1 to 5). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 1991 / 009882 [Patent Document 2] International Publication No. 2019 / 210026 [Patent Document 3] International Publication No. 2019 / 210030 [Patent Document 4] International Publication No. 1997 / 035893 [Patent Document 5] Japanese Patent Publication No. 2022-069397 Summary of the Invention [Problem to be solved by the invention]

[0005] However, conventional borate compounds have room for further improvement in terms of olefin polymerization activity. In view of the above-mentioned conventional techniques, the present invention aims to provide a novel Group 13 element-containing compound that is useful as a co-catalyst in an olefin polymerization catalyst and also has excellent activating performance for the transition metal complex that is the main catalyst. [Means for solving the problem]

[0006] The present invention relates to, for example, the following [1] to [4]. [1] A compound (A) containing a Group 13 element represented by the following general formula (A): [α] γ+ {β} γ- …(A) [In the general formula (A), γ is an integer of 1 to 5. [α] γ+ is a cation represented by the following general formula (α-1), (α-2) or (α-3). [(R 1 )3NH] + …(α-1) [(R 2 )3C] + …(α-2) [(R 3 )3N-R 4 -N(R 3 )3] γ+ …(α-3) (In the general formulae (α-1), (α-2) and (α-3), a plurality of R 1 , R 2 , and R 3are each independently a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a sulfanyl group, a hydrocarbon group having 1 to 30 carbon atoms, a heteroatom-containing hydrocarbon group, or a group in which some or all of the carbon atoms of the hydrocarbon group or heteroatom-containing hydrocarbon group have been replaced with silicon atoms or germanium atoms, and may be bonded to each other to form a ring. 4 is a hydrocarbon group having 1 to 30 carbon atoms or a hydrocarbon group containing a hetero atom, and R 4 and one or more R 3 may be bonded to each other to form a ring. {β} γ- represents one or more anions (β), and the total valence of the anions (β) is γ. The anions (β) are anions (β-1) represented by the following general formula (β-1) or anions (β-2) other than the anions (β-1): [MQ4] - …(β-1) (In the general formula (β-1), M is an atom of a Group 13 element. The four Qs are independently aryl groups, and at least one of the four Qs is an aryl group (Q-0) having one or more halogen atoms selected from a chlorine atom, a bromine atom, and an iodine atom as a substituent. At least one of the anions (β) is the anion (β-1). When a plurality of anions (β) are present, they may be the same or different.

[0007] [2] The Group 13 element-containing compound (A) according to [1], wherein in the general formula (A), at least one of the aryl groups (Q-0) is an aryl group represented by the following general formula (Q-1):

[0008] [ka] In the general formula (Q-1), * represents a bond to the M, and a plurality of X aare independently halogen atoms selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and two X's located at meta positions with respect to the bond to M are a At least one of the groups is a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom.

[0009] [3] The Group 13 element-containing compound (A) according to [2], wherein the aryl group represented by the general formula (Q-1) is an aryl group represented by the following general formula (Q-1a) or (Q-1b):

[0010] [ka] In general formulae (Q-1a) and (Q-1b), * represents a bond to M, and multiple X m are independently a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom.

[0011] [4] The Group 13 element-containing compound (A) according to any one of [1] to [3], wherein in the general formula (A), M is a boron atom. [Effects of the Invention]

[0012] According to the present invention, there is provided a novel Group 13 element-containing compound which is useful as a co-catalyst in an olefin polymerization catalyst and which also has excellent activating properties for the transition metal complex which is the main catalyst. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present invention will now be described in further detail. [Group 13 element-containing compound (A)] The Group 13 element-containing compound (A) according to the present invention (hereinafter also simply referred to as "compound (A)") is characterized by being represented by the following general formula (A). [α] γ+ {β} γ- …(A) [In general formula (A), [α] γ+ is a given cation. {β} γ- is a predetermined anion.

[0014] <γ> In the general formula (A), γ is an integer of 1 to 5, preferably an integer of 1 to 3, and more preferably an integer of 1 to 2.

[0015] <[α] γ+ > In general formula (A), [α] γ+ is a cation represented by the following general formula (α-1), (α-2) or (α-3). [(R 1 )3NH] + …(α-1) [(R 2 )3C] + …(α-2) [(R 3 )3N-R 4 -N(R 3 )3] γ+ …(α-3)

[0016] 《R 1 , R 2 , R 3 》 In the general formulae (α-1), (α-2) and (α-3), a plurality of R 1 , R 2 , and R 3 are each independently a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a sulfanyl group, a hydrocarbon group having 1 to 30 carbon atoms, a heteroatom-containing hydrocarbon group, or a group in which some or all of the carbon atoms of the hydrocarbon group or heteroatom-containing hydrocarbon group have been substituted with silicon atoms or germanium atoms. 1 Comrade, R 2 R 3 may be the same or different and may be bonded to each other to form a ring.

[0017] (halogen atom) Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0018] (hydrocarbon group) Examples of the hydrocarbon group include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. An alicyclic hydrocarbon group may contain an aliphatic hydrocarbon moiety, and an aromatic hydrocarbon group may contain an aliphatic hydrocarbon moiety and / or an alicyclic hydrocarbon moiety.

[0019] The hydrocarbon group may or may not have an unsaturated bond, and the aliphatic hydrocarbon group may be linear or branched. Specific examples of the hydrocarbon group include: Methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-octadecyl, n-icosyl, isopropyl, sec-butyl, tert-butyl, isobutyl, pentan-2-yl, 2-methylbutyl, isopentyl, neopentyl, tert-pentyl (1,1-dimethylpropyl), cyamyl, pentan-3-yl, 2-methylpentyl, 3-methylpentyl, isohexyl, 1,1-dimethylbutyl (2-methylpentan-2-yl), 3-methylpentan-2-yl linear or branched alkyl groups having 1 to 30 carbon atoms, such as a 4-methylpentan-2-yl group, a 2,2-dimethylbutyl group, a 2,3-dimethylbutyl group, a 3,3-dimethylbutyl group, a thexyl group, a 3-methylpentan-3-yl group, a 3,3-dimethylbut-2-yl group, a hexane-3-yl group, a 2-methylpentan-3-yl group, a heptan-4-yl group, a 2,4-dimethylpentan-2-yl group, a 3-ethylpentan-3-yl group, a 4,4-dimethylpentyl group, a 4-methylheptan-4-yl group, a 4-propylheptan-4-yl group, a 2,3,3-trimethylbutan-2-yl group, or a 2,4,4-trimethylpentan-2-yl (tert-octyl group); Vinyl group, allyl group, propenyl group, isopropenyl group, allenyl group, but-3-en-1-yl group, crotyl group, but-3-en-2-yl group, methallyl group, but-1,3-dienyl group, pent-4-en-1-yl group, pent-3-en-1-yl group, pent-2-en-1-yl group, isopentenyl group, 2-methylbut-3-en-1-yl group, pent-4-en-2-yl group, prenyl group, 2-methyl-but-2-en-1- yl group, pent-3-en-2-yl group, 2-methyl-but-3-en-2-yl group, pent-1-en-3-yl group, penta-2,4-dien-1-yl group, penta-1,3-dien-1-yl group, penta-1,4-dien-3-yl group, iso-prenyl group (2-methyl-but-1,3-dien-1-yl group), penta-2,4-dien-2-yl group, hex-5-en-1-yl group, hex-4-en-1-yl group, hex-3-en- 1-yl group, hex-2-en-1-yl group, 4-methyl-pent-4-en-1-yl group, 3-methyl-pent-4-en-1-yl group, 2-methyl-pent-4-en-1-yl group, hex-5-en-2-yl group, 4-methyl-pent-3-en-1-yl group, 3-methyl-pent-3-en-1-yl group, 2,3-dimethyl-but-2-en-1-yl group, 2-methylpent-4-en-2-yl group, 3-ethyl-pent-1-en-3 linear or branched alkenyl groups or unsaturated double bond-containing groups having 2 to 30 carbon atoms, such as a 2-(cyclopentadienyl)-yl group, a hexa-3,5-dien-1-yl group, a hexa-2,4-dien-1-yl group, a 4-methylpenta-1,3-dien-1-yl group, a 2,3-dimethyl-buta-1,3-dien-1-yl group, a hexa-1,3,5-trien-1-yl group, a 2-(cyclopentadienyl)propan-2-yl group, or a 2-(cyclopentadienyl)ethyl group; Ethynyl group, prop-2-yn-1-yl group, propargyl group, but-1-yn-1-yl group, but-2-yn-1-yl group, but-3-yn-1-yl group, pent-1-yn-1-yl group, pent-2-yn-1-yl group, pent-3-yn-1-yl group, pent-4-yn-1-yl group, 3-methyl-but-1-yn-1-yl group, pent-3-yn-2-yl group, 2-methyl-but-3-yn-1-yl group linear or branched alkynyl groups or unsaturated triple bond-containing groups having 2 to 30 carbon atoms, such as pent-1-yn-yl, pent-4-yn-2-yl, hex-1-yn-1-yl, 3,3-dimethyl-but-1-yn-1-yl, 2-methyl-pent-3-yn-2-yl, 2,2-dimethyl-but-3-yn-1-yl, hex-4-yn-1-yl, and hex-5-yn-1-yl; Benzyl group, 2-methylbenzyl group, 4-methylbenzyl group, 2,4,6-trimethylbenzyl group, 3,5-dimethylbenzyl group, cuminyl group, 2,4,6-tri-isopropylbenzyl group, 4-tert-butylbenzyl group, 3,5-di-tert-butylbenzyl group, 1-phenylethyl group, benzhydryl group, cumyl group (2-phenylpropan-2-yl group), 2-(4-methylphenyl)propan-2-yl group, 2-(3,5-dimethylphenyl)propan-2-yl group, 2-(4-tert-butylphenyl)propan-2-yl group, 2-(3,5-di-tert-butylphenyl)propan-2-yl group, 3-phenylpentan-3-yl group, 4-phenylhepta-1, 6-dien-4-yl group, 1,2,3-triphenylpropan-2-yl group, 1,1-diphenylethyl group, 1,1-diphenylpropyl group, 1,1-diphenyl-but-3-en-1-yl group, 1,1,2-triphenylethyl group, trityl group (triphenylmethyl group), tri-(4-methylphenyl)methyl group, 2-phenylethyl group, styryl group (2-phenylvinyl group), 2-(2-methylphenyl)ethyl group, 2-(4-methylphenyl)ethyl group, 2-(2,4,6-trimethylphenyl)ethyl group, 2-(3,5-dimethylphenyl)ethyl group, 2-(2,4,6-tri-isopropylphenyl)ethyl group, 2-(4-tert-butylphenyl)ethyl group, 2-(3,(5-di-tert-butylphenyl)ethyl group, 2-methyl-1-phenylpropan-2-yl group, 3-phenylpropyl group, cinnamyl group (3-phenylallyl group), neophyl group (2-methyl-2-phenylpropyl group), 3-methyl-3-phenylbutyl group, 2-methyl-4-phenylbutan-2-yl group, cyclopentadienyldiphenylmethyl group, 2-(1-indenyl)propan-2-yl group, (1-indenyl)diphenylmethyl group, 2-(1-indenyl)ethyl group, 2-(tetrahydro-1-indacenyl)propan-2-yl group, (tetrahydro-1-indacenyl ) Aromatic-containing linear or branched alkyl groups and unsaturated double bond-containing groups having 7 to 30 carbon atoms, such as diphenylmethyl group, 2-(tetrahydro-1-indacenyl)ethyl group, 2-(1-benzoindenyl)propan-2-yl group, (1-benzoindenyl)diphenylmethyl group, 2-(1-benzoindenyl)ethyl group, 2-(9-fluorenyl)propan-2-yl group, (9-fluorenyl)diphenylmethyl group, 2-(9-fluorenyl)ethyl group, 2-(1-azulenyl)propan-2-yl group, (1-azulenyl)diphenylmethyl group, and 2-(1-azulenyl)ethyl group; Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclopentenyl group, cyclopentadienyl group, dimethylcyclopentadienyl group, n-butylcyclopentadienyl group, n-butyl-methylcyclopentadienyl group, tetramethylcyclopentadienyl group, 1-methylcyclopentyl group, 1-allylcyclopentyl group, 1-benzylcyclopentyl group, cyclohexyl group, cyclohexenyl group, cyclohexadienyl group, 1-methylcyclohex Sil group, 1-allylcyclohexyl group, 1-benzylcyclohexyl group, cycloheptyl group, cycloheptenyl group, cycloheptatrienyl group, 1-methylcycloheptyl group, 1-allylcycloheptyl group, 1-benzylcycloheptyl group, cyclooctyl group, cyclooctenyl group, cyclooctadienyl group, cyclooctatrienyl group, 1-methylcyclooctyl group, 1-allylcyclooctyl group, 1-benzylcyclooctyl group, 4-cyclohexyl- tert-butyl group, norbornyl group, norbornenyl group, norbornadienyl group, 2-methylbicyclo[2.2.1]heptan-2-yl group, 7-methylbicyclo[2.2.1]heptan-7-yl group, bicyclo[2.2.2]octan-1-yl group, bicyclo[2.2.2]octan-2-yl group, 1-adamantyl group, 2-adamantyl group, 1-(2-methyladamantyl), 1-(3-methyladamantyl), 1-(4-methyladamantyl), 1 cyclic saturated and unsaturated hydrocarbon groups having 3 to 30 carbon atoms, such as -(2-phenyladamantyl), 1-(3-phenyladamantyl), 1-(4-phenyladamantyl), 1-(3,5-dimethyladamantyl), 1-(3,5,7-trimethyladamantyl), 1-(3,5,7-triphenyladamantyl), pentalenyl, indenyl, fluorenyl, indacenyl, tetrahydroindacenyl, benzoindenyl, and azulenyl; Phenyl group, tolyl group (o-tolyl group, m-tolyl group, p-tolyl group), 4-n-butylphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n-undecylphenyl group, 4-n-dodecylphenyl group, 4-n-octadecylphenyl group, 4-iso-propylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4-iso-butylphenyl group, 4-iso- Pentylphenyl group, 4-neopentylphenyl group, 4-tert-pentylphenyl group, 4-(pentan-3-yl)phenyl group, 4-iso-hexylphenyl group, 4-(1,1-dimethylbutyl)phenyl group, 4-(3,3-dimethylbutyl)phenyl group, 4-thexylphenyl group, 4-(3-methylpentan-3-yl)phenyl group, 4-(heptan-4-yl)phenyl group, 4-(2,4-dimethylpentan-2-yl)phenyl group, 4-(3-ethylpentan-3-yl)phenyl group, 4-(4,4-dimethylpentyl)phenyl group nyl group, 4-(4-methylheptan-4-yl)phenyl group, 4-(4-propylheptan-4-yl)phenyl group, 4-(2,4,4-trimethylpentan-2-yl)phenyl group, 4-adamantylphenyl group, 3-n-butylphenyl group, 3-n-pentylphenyl group, 3-n-hexylphenyl group, 3-n-heptylphenyl group, 3-n-octylphenyl group, 3-n-nonylphenyl group, 3-n-decylphenyl group, 3-n-undecylphenyl group, 3-n-dodecylphenyl group, 3-n-octadecylphenyl group, 3-is o-Propylphenyl group, 3-sec-butylphenyl group, 3-tert-butylphenyl group, 3-iso-butylphenyl group, 3-iso-pentylphenyl group, 3-neopentylphenyl group, 3-tert-pentylphenyl group, 3-(pentan-3-yl)phenyl group, 3-iso-hexylphenyl group, 3-(1,1-dimethylbutyl)phenyl group, 3-(3,3-dimethylbutyl)phenyl group, 3-thexylphenyl group, 3-(3-methylpentan-3-yl)phenyl group, 3-(heptan-4-yl)phenyl group, 3-(2,4-dimethylpentan-2-yl)phenyl group, 3-(3-ethylpentan-3-yl)phenyl group, 3-(4,4-dimethylpentyl)phenyl group, 3-(4-methylheptan-4-yl)phenyl group, 3-(4-propylheptan-4-yl)phenyl group, 3-(2,4,4-trimethylpentan-2-yl)phenyl group, 3-adamantylphenyl group, 2-n-butylphenyl group, 2-n-pentylphenyl group, 2-n-hexylphenyl group, 2-n-heptylphenyl group, 2-n-octylphenyl group, 2-n-nonylphenyl group, 2-n-decylphenyl group, 2-n-undecylphenyl group, 2-n-dodecylphenyl group, 2-n-octadecylphenyl group, 2-iso-propylphenyl group, 2-sec-butylphenyl group, 2-tert-butylphenyl group, 2-iso-butylphenyl group, 2-iso-pentylphenyl group, 2-neopentylphenyl group, 2-tert-pentylphenyl group, 2-(pentan-3-yl)phenyl group, 2-iso-hexylphenyl group, 2-(1,1-dimethylbutyl)phenyl group, 2-(3,3-dimethylbutyl)phenyl group nyl group, 2-thexylphenyl group, 2-(3-methylpentan-3-yl)phenyl group, 2-(heptan-4-yl)phenyl group, 2-(2,4-dimethylpentan-2-yl)phenyl group, 2-(3-ethylpentan-3-yl)phenyl group, 2-(4,4-dimethylpentyl)phenyl group, 2-(4-methylheptan-4-yl)phenyl group, 2-(4-propylheptan-4-yl)phenyl group, 2-(2,4,4-trimethylpentan-2-yl)phenyl group, 2-adamantylphenyl group, xylyl group (2,3-dimethylphenyl) n-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl), 3,5-di-tert-butylphenyl, 3,5-di-n-octylphenyl, 3,5-di-n-dodecylphenyl, 3,5-di-n-octadecylphenyl, 3,5-di(2,4,4-trimethylpentan-2-yl)phenyl, 3,5-diadamantylphenyl, mesityl, cumenyl, duralyl, 2,6-di-isopropylphenyl, 2,4,Examples of aromatic substituents having 6 to 30 carbon atoms include a 6-tri-isopropylphenyl group, an allylphenyl group, a (but-3-en-1-yl)phenyl group, a (but-2-en-1-yl)phenyl group, a methallylphenyl group, a prenylphenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a binaphthyl group, an acenaphthalenyl group, a phenanthryl group, an anthracenyl group, a pyrenyl group, and a ferrocenyl group.

[0020] Among the linear or branched alkyl groups having 1 to 30 carbon atoms, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-octadecyl group, an isopropyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a pentan-3-yl group, an isohexyl group, a 1,1-dimethylbutyl group, a 3,3-dimethylbutyl group, a thexyl group, a 3-methylpentan-3-yl group, a heptane-4-yl group, a methyl group, an ethyl group, an n-propyl group, an ethyl group, an n-pentyl group, an ethyl ... Preferred are methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-dodecyl, n-octadecyl, isopropyl, tert-butyl, neopentyl, 2,4-dimethylpentan-2-yl, 2,4,4-trimethylpentan-2-yl, and the like, and more preferred are hydrocarbon groups having 1 to 20 carbon atoms, such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-dodecyl, n-octadecyl, isopropyl, tert-butyl, neopentyl, 2,4-dimethylpentan-2-yl, 2,4,4-trimethylpentan-2-yl, and tert-octyl. When the number of carbon atoms in the hydrocarbon group is reduced, compound (A) tends to have a lower affinity with the hydrocarbon medium when used as a catalyst component in the hydrocarbon medium, which improves catalyst immobilization and activation performance.

[0021] Among the linear or branched alkenyl groups or unsaturated double bond-containing groups having 2 to 30 carbon atoms, a vinyl group, an allyl group, a but-3-en-1-yl group, a crotyl group, a methallyl group, a pent-4-en-1-yl group, a prenyl group, a penta-1,4-dien-3-yl group, a hex-5-en-1-yl group, a 2-methylpent-4-en-2-yl group, a 2-(cyclopentadienyl)propan-2-yl group, a 2-(cyclopentadienyl)ethyl group, and the like are preferred, and a vinyl group, an allyl group, a but-3-en-1-yl group, a pent-4-en-1-yl group, a prenyl group, and a hex-5-en-1-yl group are more preferred.

[0022] Among the linear or branched alkynyl groups or unsaturated triple bond-containing groups having 2 to 30 carbon atoms, an ethynyl group, a propargyl group, a but-2-yn-1-yl group, a but-3-yn-1-yl group, a penta-3-yn-1-yl group, a penta-4-yn-1-yl group, a 3-methyl-but-1-yn-1-yl group, a 3,3-dimethyl-but-1-yn-1-yl group, a hex-4-yn-1-yl group, a hex-5-yn-1-yl group, and the like are preferred, and a propa-2-yn-1-yl group, a propargyl group, a but-2-yn-1-yl group, and a but-3-yn-1-yl group are more preferred.

[0023] Among the aromatic-containing linear or branched alkyl groups and unsaturated double bond-containing groups having 7 to 30 carbon atoms, benzyl group, 2-methylbenzyl group, 4-methylbenzyl group, 2,4,6-trimethylbenzyl group, 3,5-dimethylbenzyl group, cuminyl group, 2,4,6-tri-isopropylbenzyl group, 4-tert-butylbenzyl group, 3,5-di-tert-butylbenzyl group, benzhydryl group, cumyl group, 1,1-diphenylethyl group, trityl group, 2-phenylethyl group, 2-(4-methylphenyl)ethyl group, 2-(2,4,6-trimethylphenyl)ethyl group, 2-(3,5-dimethylphenyl)ethyl group, 2-(2,4,6-tri-isopropylphenyl)ethyl group, 2-(4-t Preferred are a 2-(3,5-di-tert-butylphenyl)ethyl group, a 2-(3,5-di-tert-butylphenyl)ethyl group, a styryl group, a 2-methyl-1-phenylpropan-2-yl group, a 3-phenylpropyl group, a cinnamyl group, a neophyl group, a cyclopentadienyldiphenylmethyl group, a 2-(1-indenyl)propan-2-yl group, a (1-indenyl)diphenylmethyl group, a 2-(1-indenyl)ethyl group, a 2-(9-fluorenyl)propan-2-yl group, a (9-fluorenyl)diphenylmethyl group, and a 2-(9-fluorenyl)ethyl group, and more preferred are a benzyl group, a benzhydryl group, a cumyl group, a 1,1-diphenylethyl group, a trityl group, a 2-phenylethyl group, a 3-phenylpropyl group, and a cinnamyl group.

[0024] Among the above-mentioned saturated and unsaturated cyclic hydrocarbon groups having 3 to 30 carbon atoms, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclopentenyl group, a cyclopentadienyl group, a 1-methylcyclopentyl group, a 1-allylcyclopentyl group, a 1-benzylcyclopentyl group, a cyclohexyl group, a cyclohexenyl group, a 1-methylcyclohexyl group, a 1-allylcyclohexyl group, a 1-benzylcyclohexyl group, a cycloheptyl group, a cycloheptenyl group, a cycloheptatrienyl group, a 1-methylcycloheptyl group, a 1-allylcycloheptyl group, a 1-benzylcyclopentyl group, a cyclohexyl group, a cyclohexenyl group, a cycloheptyl group, a cycloheptatrienyl group, a 1-methylcycloheptyl group, a 1-allylcycloheptyl group, a cyclohex ... Preferred are cycloheptyl, cyclooctyl, cyclooctenyl, cyclooctadienyl, 4-cyclohexyl-tert-butyl, norbornyl, 2-methylbicyclo[2.2.1]heptan-2-yl, bicyclo[2.2.2]octan-1-yl, 1-adamantyl, 2-adamantyl, pentalenyl, indenyl, and fluorenyl groups, and more preferred are cyclopentyl, cyclopentenyl, 1-methylcyclopentyl, cyclohexyl, cyclohexenyl, 1-methylcyclohexyl, and 1-adamantyl groups.

[0025] Among the aromatic substituents having 6 to 30 carbon atoms, a phenyl group, a tolyl group, a 4-n-hexylphenyl group, a 4-n-heptylphenyl group, a 4-n-octylphenyl group, a 4-n-decylphenyl group, a 4-n-dodecylphenyl group, a 4-n-octadecylphenyl group, a 4-tert-butylphenyl group, a 4-(2,4,4-trimethylpentan-2-yl)phenyl group, a 4-adamantylphenyl group, a 3-n-hexylphenyl group, a 3-n-hept ... Phenyl group, 3-n-octylphenyl group, 3-n-decylphenyl group, 3-n-dodecylphenyl group, 3-n-octadecylphenyl group, 3-tert-butylphenyl group, 3-(2,4,4-trimethylpentan-2-yl)phenyl group, 3-adamantylphenyl group, xylyl group, 3,5-di-tert-butylphenyl group, 3,5-di-n-octylphenyl group, 3,5-di-n-dodecylphenyl group, 3,5-di-n-octadecylphenyl group Preferred are an aryl group, a 3,5-di(2,4,4-trimethylpentan-2-yl)phenyl group, a 3,5-diadamantylphenyl group, a mesityl group, a cumenyl group, a 2,6-di-isopropylphenyl group, a 2,4,6-tri-isopropylphenyl group, an allylphenyl group, a prenylphenyl group, a 4-adamantylphenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a binaphthyl group, a phenanthryl group, an anthracenyl group, and a ferrocenyl group. More preferred are a phenyl group, a tolyl group, a xylyl group, a mesityl group, a cumenyl group, a 2,6-di-isopropylphenyl group, a 2,4,6-tri-isopropylphenyl group, a 4-tert-butylphenyl group, a 3,5-di-tert-butylphenyl group, a 4-(2,4,4-trimethylpentan-2-yl)phenyl group, an allylphenyl group, a 4-adamantylphenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, and an anthracenyl group.

[0026] (heteroatom-containing hydrocarbon group) One example of the heteroatom-containing hydrocarbon group is one in which some or all of the hydrogen atoms in the hydrocarbon group have been replaced with halogen atoms or a heteroatom-containing group. Examples of the heteroatom-containing group include an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, and a phosphorus-containing group.

[0027] Examples of the groups substituted with halogen atoms include a fluoromethyl group, a trifluoromethyl group, a trichloromethyl group, a tribromomethyl group, a triiodomethyl group, a pentafluoroethyl group, a pentachloroethyl group, a 2,2,2-trifluoroethyl group, a heptafluoropropyl group, a 3,3,3-trifluoropropyl group, a nonafluorobutyl group, a nonachlorobutyl group, a 4,4,4-trifluorobutyl group, a dodecafluorohexyl group, a 6,6,6-trifluorohexyl group, chlorophenyl group, fluorophenyl group, bromophenyl group, iodophenyl group, difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group, pentafluorophenyl group, pentachlorophenyl group, pentabromophenyl group, pentaiodophenyl group, bis(trimethylsilyl)trifluorophenyl group, bis(triisopropylsilyl)trifluorophenyl group, bis(tert-butyldimethylsilyl)trifluorophenyl group, di-tert-butyl-fluorophenyl group, trifluoromethylphenyl group, di-tert-butyl-fluorophenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, bis(trifluoromethyl)fluorophenyl group, bis(trifluoromethyl)trifluorophenyl group, pentafluorobenzyl group, trifluoromethoxyphenyl group, bistrifluoromethoxyphenyl group, trifluoromethylthiophenyl group, bistrifluoromethylthiophenyl group, fluorobiphenyl group, difluoro Examples of such groups include a difluorobiphenyl group, a trifluorobiphenyl group, a tetrafluorobiphenyl group, a pentafluorobiphenyl group, a perfluorobiphenyl-2-yl group, a perfluorobiphenyl-3-yl group, a di-tert-butyl-fluorobiphenyl group, a trifluoromethylbiphenyl group, a bistrifluoromethylbiphenyl group, a trifluoromethoxybiphenyl group, a bistrifluoromethoxybiphenyl group, a trifluoromethyldimethylsilyl group, a trifluoromethoxy group, a pentafluoroethoxy group, a fluorophenoxy group, a difluorophenoxy group, a trifluorophenoxy group, a pentafluorophenoxy group, a di-tert-butyl-fluorophenoxy group, a trifluoromethylphenoxy group, a bistrifluoromethylphenoxy group, a trifluoromethoxyphenoxy group, a bistrifluoromethoxyphenoxy group, a difluoromethylenedioxyphenyl group, a bistrifluoromethylphenyliminomethyl group, a trifluoromethylthio group, an α-perfluoronaphthyl group, and a β-perfluoronaphthyl group.

[0028] Among those substituted with halogen atoms, a fluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, a fluorophenyl group, a difluorophenyl group, a trifluorophenyl group, a tetrafluorophenyl group, a pentafluorophenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a trifluoromethoxyphenyl group, a pentafluorobiphenyl group, a trifluoromethylbiphenyl group, a bistrifluoromethylbiphenyl group, a trifluoromethoxy group, a pentafluorophenoxy group, a bistrifluoromethylphenoxy group, a bistrifluoromethylphenoxy group, a difluoromethylenedioxyphenyl group, and a trifluoromethylthio group are preferred, and a trifluoromethyl group, a fluorophenyl group, a pentafluorophenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a pentafluorobiphenyl group, a trifluoromethoxy group, and a pentafluorophenoxy group are more preferred.

[0029] Examples of the oxygen-containing group include a hydroxymethyl group, a hydroxyethyl group, a 2-hydroxydodecyl group, a 2-hydroxyoctadecyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an allyloxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, a tert-butoxy group, a methallyloxy group, a prenyloxy group, an octyloxy group, a tert-octyloxy group, a decyloxy group, a dodecyloxy group, an octa ... Decyloxy group, benzyloxy group, methoxymethoxy group, methoxyethoxy group, phenoxy group, naphthoxy group, toluyloxy group, isopropylphenoxy group, allylphenoxy group, tert-butylphenoxy group, methoxyphenoxy group, isopropoxyphenoxy group, allyloxyphenoxy group, biphenyloxy group, binaphthyloxy group, methoxymethyl group, allyloxymethyl group, benzyloxymethyl group, phenoxymethyl group, methoxy Examples of such groups include a diethyl group, an allyloxyethyl group, a benzyloxyethyl group, a phenoxyethyl group, a methoxypropyl group, an allyloxypropyl group, a benzyloxypropyl group, a phenoxypropyl group, a methoxyvinyl group, an allyloxyvinyl group, a benzyloxyvinyl group, a phenoxyvinyl group, a methoxyallyl group, an allyloxyallyl group, a benzyloxyallyl group, a phenoxyallyl group, a dimethoxymethyl group, a di-iso-propoxymethyl group, a dioxolanyl group, a tetramethyldioxolanyl group, a dioxanyl group, a methoxyphenyl group, an iso-propoxyphenyl group, an allyloxyphenyl group, a phenoxyphenyl group, a methylenedioxyphenyl group, a 3,5-dimethyl-4-methoxyphenyl group, a 3,5-di-tert-butyl-4-methoxyphenyl group, a furyl group, a methylfuryl group, a tetrahydrofuryl group, a pyranyl group, a tetrahydropyranyl group, a furofuryl group, a benzofuryl group, and a dibenzofuryl group.

[0030] Among the oxygen-containing groups, a hydroxymethyl group, a hydroxyethyl group, a 2-hydroxydodecyl group, a 2-hydroxyoctadecyl group, a methoxy group, an ethoxy group, an isopropoxy group, an allyloxy group, an n-butoxy group, a tert-butoxy group, a prenyloxy group, an octyloxy group, a tert-octyloxy group, a decyloxy group, a dodecyloxy group, an octadecyloxy group, a benzyloxy group, a phenoxy group, a naphthoxy group, a toluyloxy group, an isopropylphenoxy group, a oxy group, allylphenoxy group, tert-butylphenoxy group, methoxyphenoxy group, biphenyloxy group, binaphthyloxy group, allyloxymethyl group, benzyloxymethyl group, phenoxymethyl group, methoxyethyl group, methoxymethoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-(2-ethoxyethoxy)ethoxy group, methoxyallyl group, benzyloxyallyl group, phenoxyallyl group, dimethoxymethyl group, dioxolanyl group, tetramethyldioxolanyl group, A xolanyl group, a dioxanyl group, a dimethyldioxanyl group, a methoxyphenyl group, an isopropoxyphenyl group, an allyloxyphenyl group, a phenoxyphenyl group, a methylenedioxyphenyl group, a 3,5-dimethyl-4-methoxyphenyl group, a 3,5-di-tert-butyl-4-methoxyphenyl group, a furyl group, a methylfuryl group, a tetrahydropyranyl group, a furofuryl group, a benzofuryl group, a dibenzofuryl group, and the like are preferred, and a hydroxyethyl group, a 2-hydroxydodecanyl group, and the like are also preferred. A sil group, a 2-hydroxyoctadecyl group, a methoxy group, an iso-propoxy group, a tert-butoxy group, an allyloxy group, a phenoxy group, a dimethoxymethyl group, a dioxolanyl group, a methoxyphenyl group, an iso-propoxyphenyl group, an allyloxyphenyl group, a phenoxyphenyl group, a 3,5-dimethyl-4-methoxyphenyl group, a 3,5-di-tert-butyl-4-methoxyphenyl group, a furyl group, a methylfuryl group, a benzofuryl group, and a dibenzofuryl group are more preferred.

[0031] Examples of the nitrogen-containing group include a dimethylamino group, a diethylamino group, an allylamino group, a diallylamino group, an N,N-dihexylamino group, an N,N-didecylamino group, an N,N-didodecylamino group, an N,N-dioctadecylamino group, a benzylamino group, a dibenzylamino group, a pyrrolidinyl group, a piperidinyl group, a morpholyl group, an azepinyl group, a dimethylaminomethyl group, a dibenzylaminomethyl group, a pyrrolidinylmethyl group, a dimethylaminoethyl group, a benzylaminomethyl group, a benzylaminoethyl group, a pyrrolidinylethyl group, a dimethylaminovinyl group, a benzylaminovinyl group, a pyrrolidinylvinyl group, a dimethylaminopropyl group, a benzylaminopropyl group, a pyrrolidinylpropyl group, a dimethylaminoallyl group, a benzylaminoallyl group, a pyrrolidinylallyl group, an aminophenyl group, a dimethylaminophenyl group, a 3, Examples of such groups include a 5-dimethyl-4-dimethylaminophenyl group, a 3,5-di-isopropyl-4-dimethylaminophenyl group, a julolidinyl group, a tetramethyljulolidinyl group, a pyrrolidinylphenyl group, a pyrrolylphenyl group, a pyridylphenyl group, a quinolylphenyl group, an isoquinolylphenyl group, an indolinylphenyl group, an indolylphenyl group, a carbazolylphenyl group, a di-tert-butylcarbazolylphenyl group, a pyrrolyl group, a methylpyrrolyl group, a phenylpyrrolyl group, a pyridyl group, a quinolyl group, a tetrahydroquinolyl group, an isoquinolyl group, a tetrahydro-isoquinolyl group, an indolyl group, an indolinyl group, a carbazolyl group, a di-tert-butylcarbazolyl group, an imidazolyl group, a dimethylimidazolidinyl group, a benzimidazolyl group, an oxazolyl group, an oxazolidinyl group, and a benzoxazolyl group.

[0032] Among the nitrogen-containing groups, an amino group, a dimethylamino group, a diethylamino group, an allylamino group, a benzylamino group, a dibenzylamino group, a pyrrolidinyl group, a piperidinyl group, a morpholyl group, a dimethylaminomethyl group, a benzylaminomethyl group, a pyrrolidinylmethyl group, a dimethylaminoethyl group, a pyrrolidinylethyl group, a dimethylaminopropyl group, a pyrrolidinylpropyl group, a dimethylaminoallyl group, a pyrrolidinylallyl group, an aminophenyl group, a dimethylaminophenyl group, a 3,5-dimethyl-4-dimethylaminophenyl group, a 3,5-di-iso-propyl-4-dimethylaminophenyl group, a julolidinyl group, a tetramethyljulolidinyl group, a pyrrolidinylphenyl group, a pyrrolylphenyl group, a carbazolylphenyl group, a di-tert-butylcarbazolyl group, A phenyl group, a pyrrolyl group, a pyridyl group, a quinolyl group, a tetrahydroquinolyl group, an isoquinolyl group, a tetrahydro-isoquinolyl group, an indolyl group, an indolinyl group, a carbazolyl group, a di-tert-butylcarbazolyl group, an imidazolyl group, a dimethylimidazolidinyl group, a benzimidazolyl group, an oxazolyl group, an oxazolidinyl group, a benzoxazolyl group, and the like are preferred, and an amino group, a dimethylamino group, a diethylamino group, a pyrrolidinyl group, a dimethylaminophenyl group, a 3,5-dimethyl-4-dimethylaminophenyl group, a 3,5-di-isopropyl-4-dimethylaminophenyl group, a julolidinyl group, a tetramethyljulolidinyl group, a pyrrolidinylphenyl group, a pyrrolyl group, a pyridyl group, a carbazolyl group, and an imidazolyl group are more preferred.

[0033] Examples of the sulfur-containing group include a methylthio group, an ethylthio group, a benzylthio group, a phenylthio group, a naphthylthio group, a methylthiomethyl group, a benzylthiomethyl group, a phenylthiomethyl group, a naphthylthiomethyl group, a methylthioethyl group, a benzylthioethyl group, a phenylthioethyl group, a naphthylthioethyl group, a methylthiovinyl group, a benzylthiovinyl group, a phenylthiovinyl group, a naphthylthiovinyl group, a methylthiopropyl group, a benzylthiopropyl group, a phenylthiopropyl group, a naphthylthiopropyl group, a methylthioallyl group, a benzylthioallyl group, a phenylthio Examples of such groups include a thioallyl group, a naphthylthioallyl group, a mercaptophenyl group, a methylthiophenyl group, a thienylphenyl group, a methylthienylphenyl group, a benzothienylphenyl group, a dibenzothienylphenyl group, a benzodithienylphenyl group, a thienyl group, a tetrahydrothienyl group, a methylthienyl group, a thienofuryl group, a thienothienyl group, a benzothienyl group, a dibenzothienyl group, a thienobenzofuryl group, a benzodithienyl group, a dithiolanyl group, a dithianyl group, an oxathiolanyl group, an oxathianyl group, a thiazolyl group, a benzothiazolyl group, and a thiazolidinyl group.

[0034] Among the sulfur-containing groups, a thienyl group, a methylthienyl group, a thienofuryl group, a thienothienyl group, a benzothienyl group, a dibenzothienyl group, a thienobenzofuryl group, a benzodithienyl group, a thiazolyl group, and a benzothiazolyl group are preferred.

[0035] Examples of the phosphorus-containing group include a dimethylphosphino group, a diethylphosphino group, a di-n-propylphosphino group, a diisopropylphosphino group, a dicyclopentylphosphino group, a dicyclohexylphosphino group, a di(methylcyclohexyl)phosphino group, a di-n-butylphosphino group, a di-sec-butylphosphino group, a di-tert-butylphosphino group, an ethyldecylphosphino group, a diundecylphosphino group, a didodecylphosphino group, a methyldodecylphosphino group, a dioctadecylphosphino group, a diphenylphosphino group, a di(o-tolyl)phosphino group, a di(m-tolyl)phosphino group, a di(p-tolyl)phosphino group, a di(pentafluorophenyl)phosphino group, and a di(trifluoromethyl)phosphino group.

[0036] Among the phosphorus-containing groups, a dioctadecylphosphino group and a di(pentafluorophenyl)phosphino group are preferred.

[0037] Other examples of the heteroatom-containing hydrocarbon group include groups in which some of the methylene groups in the hydrocarbon group have been replaced with a structure represented by -CO-, -CH(OH)-, -NR-, -PR-, -P(O)(R)- (where R is a hydrogen atom or a hydrocarbon group (having, for example, 1 to 10 carbon atoms)), -O-, -S-, or -SO2-, and groups in which some of the methine groups in the hydrocarbon group have been replaced with a nitrogen atom, a phosphorus atom, or a structure represented by ≡SiH (wherein the number of carbon atoms in the cations represented by general formulae (α-1), (α-2), and (α-3) is selected within a range such that the number of carbon atoms is 30 or less).

[0038] Other examples of the heteroatom-containing hydrocarbon group include residues obtained by removing two hydrogen atoms from a polymer having a heteroatom, and examples of such polymers include polyaniline, polypyrrole, polyacrylonitrile, polyethyleneimine, and polyamide. A proton may be coordinately bonded to some or all of the heteroatoms (preferably nitrogen atoms) contained in the heteroatom-containing hydrocarbon group.

[0039] (Groups in which some or all of the carbon atoms of the hydrocarbon groups and heteroatom-containing hydrocarbon groups have been replaced with silicon atoms and germanium atoms) Examples of the substituent include a silyl group, a trimethylsilyl group, a triethylsilyl group, a tri-isopropylsilyl group, a diphenylmethylsilyl group, a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group, a triphenylsilyl group, a tris(trimethylsilyl)silyl group, a cyclopentadienyldimethylsilyl group, a di-n-butyl(cyclopentadienyl)silyl group, a cyclopentadienyldiphenylsilyl group, an indenyldimethylsilyl group, a di-n-butyl(indenyl)silyl group, an indenyldiphenylsilyl group, a fluorenyldimethylsilyl group, a di-n-butyl(fluorenyl)silyl group, a fluoren ... Examples thereof include an olefinyldiphenylsilyl group, a 4-trimethylsilylphenyl group, a 4-triethylsilylphenyl group, a 4-tri-isopropylsilylphenyl group, a 4-tert-butyldiphenylsilylphenyl group, a 4-triphenylsilylphenyl group, a 4-tris(trimethylsilyl)silylphenyl group, a 3,5-bis(trimethylsilyl)phenyl group, a trimethylgermyl group, a triethylgermyl group, a tert-butyldimethylgermyl group, a 4-trimethylgermylphenyl group, a 4-triethylgermylphenyl group, a 4-tri-isopropylgermylphenyl group, and a 3,5-bis(trimethylgermyl)phenyl group.

[0040] Among the above substituents, a trimethylsilyl group, a triethylsilyl group, a tri-isopropylsilyl group, a tert-butyldimethylsilyl group, and a trifluorosilyl group are more preferred.

[0041] 《R 4 》 In general formula (α-3), R 4 R is a hydrocarbon group having 1 to 30 carbon atoms or a hydrocarbon group containing a hetero atom. 4 and one or more R 3 may be bonded to each other to form a ring.

[0042] (hydrocarbon group) Examples of the hydrocarbon group include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. An alicyclic hydrocarbon group may contain an aliphatic hydrocarbon moiety, and an aromatic hydrocarbon group may contain an aliphatic hydrocarbon moiety and / or an alicyclic hydrocarbon moiety.

[0043] The hydrocarbon group may or may not have an unsaturated bond, and the aliphatic hydrocarbon group may be linear or branched. Examples of saturated aliphatic hydrocarbon groups include a methylene group; and alkylene groups such as an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a 2-methylpropylene group, a pentamethylene group, a 2-methylbutylene group, a 2-ethylpropylene group, a hexamethylene group, a 2-ethylbutylene group, a heptamethylene group, a 2-ethylpentylene group, a 2-methylhexylene group, an octamethylene group, a 2-ethylhexylene group, a nonamethylene group, a decamethylene group, an undecamethylene group, a dodecamethylene group, a tetradecamethylene group, a hexadecamethylene group, an octadecamethylene group, a 2-ethyloctadecene group, and an icosene group.

[0044] The alkylene group has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and even more preferably 2 to 6 carbon atoms.

[0045] Examples of unsaturated aliphatic hydrocarbon groups include those in which some or all of the carbon-carbon single bonds in the above-mentioned alkylene groups have been replaced with double bonds, such as groups represented by -CH=CH-, -CH2CH=CH-, -CH2CH2CH=CH-, -CH2CH=CHCH2-, -CH2C(CH3)=CH-, -CH2-C(=CH2)-CH2-, -CH(CH2CH3)-CH2CH2CH=CH-, -CH2CH2CH=CH-CH=CH-, and -CH2CH=CH-CH(CH3)-CH=CH-CH2-.

[0046] The alicyclic hydrocarbon group may be monocyclic or polycyclic, and examples thereof include a cyclopropylene group, a cyclobutane-1,2-diyl group, a cyclobutane-1,3-diyl group, a cyclopentane-1,2-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,2-diyl group, a cyclohexane-1,3-diyl group, a cyclohexane-1,4-diyl group, a 3-cyclohexene-1,2-diyl group, a 2,5-cyclohexadiene-1,4-diyl group, a cycloheptane-1,4-diyl group, a cyclooctane-1,4-diyl group, a spiro[3,4]octane-2,7-diyl group, and a spiro[4,5]deca-1,6-diene-3,9-diyl group. Further examples of groups having an aliphatic hydrocarbon moiety include groups represented by the following formula:

[0047] [ka]

[0048] The alicyclic hydrocarbon group has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and even more preferably 3 to 6 carbon atoms.

[0049] The aromatic hydrocarbon group may be monocyclic or polycyclic, and examples thereof include an o-phenylene group, a p-phenylene group, an m-phenylene group, a 1,5-naphthylene group, a 2,6-naphthylene group, a 2,7-naphthylene group, a biphenyl-4,4′-diyl group, a 1,5-anthrylene group, a 2,6-anthrylene group, an o-terphenyl-4,4″-diyl group, a p-terphenyl-4,4″-diyl group, an m-terphenyl-4,4″-diyl group, a 2,7-phenanthrylene group, and a 1,6-pyrenylene group. Further examples of groups having an aliphatic hydrocarbon moiety include groups represented by the following formula:

[0050] [ka]

[0051] The aromatic hydrocarbon group has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 carbon atoms.

[0052] (heteroatom-containing hydrocarbon group) One example of the heteroatom-containing hydrocarbon group is one in which some or all of the hydrogen atoms in the hydrocarbon group have been replaced with halogen atoms or a heteroatom-containing group. Examples of the heteroatom-containing group include a silicon-containing group, an oxygen-containing group, a nitrogen-containing group, and a sulfur-containing group, and the nitrogen-containing group is preferred.

[0053] The halogen atom or heteroatom-containing group may be substituted with the above-mentioned R 1 ~R 3 Specific examples of the heteroatom-containing hydrocarbon group in the above formula (1) are the same as those in the above formula (1).

[0054] Other examples of the heteroatom-containing hydrocarbon group include groups in which some of the methylene groups in the hydrocarbon group have been replaced with a structure represented by -CO-, -CH(OH)-, -NR-, -PR-, -P(O)(R)- (where R is a hydrogen atom or a hydrocarbon group (having, for example, 1 to 10 carbon atoms)), -O-, -S-, or -SO2-, and groups in which some of the methine groups in the hydrocarbon group have been replaced with a nitrogen atom, a phosphorus atom, or a structure represented by ≡SiH (wherein the number of carbon atoms in the cation represented by general formula (α-3) is selected within a range such that the number of carbon atoms is 30 or less).

[0055] Some or all of the heteroatoms (preferably nitrogen atoms) contained in the heteroatom-containing hydrocarbon group may have an [α] γ+ The proton may be coordinately bonded within the range in which the valence γ falls within the above range.

[0056] 《[α] γ+ Examples of [α] γ+ Specific examples of the cation include those represented by the following formula:

[0057] [ka]

[0058] <{β} γ- > In the general formula (A), {β} γ- is the above [α] γ+ represents the anion pair of {β} γ- represents one or more anions (β), and the total valence of the anions (β) is γ. The anions (β) are anions (β-1) represented by the following general formula (β-1) or anions (β-2) other than the anions (β-1): [MQ4] - …(β-1) At least one of the anions (β) is the anion (β-1). When a plurality of the anions (β) are present, they may be the same or different.

[0059] [Anion (β-1)] "M" M represents an atom of an element of Group 13. Examples of the atom of an element of Group 13 include a boron atom (B), an aluminum atom (Al), a gallium atom (Ga), an indium atom (In), and a thallium atom (Tl), of which a boron atom and an aluminum atom are preferred, and a boron atom is more preferred.

[0060] Q The four Qs are independently an aryl group, and at least one of the four Qs is an aryl group (Q-0) having one or more halogen atoms selected from a chlorine atom, a bromine atom, and an iodine atom as a substituent. Preferably, all of the four Qs are independently the aryl group (Q-0). From the viewpoint of ease of production or availability, it is more preferable that all of the four Qs are the same aryl group (Q-0).

[0061] (aryl group) Examples of the aryl group include the aromatic hydrocarbon groups having 6 to 30 carbon atoms and the aromatic hydrocarbon groups in which some or all of the hydrogen atoms have been replaced with halogen atoms or heteroatom-containing groups, and are preferably aryl groups having 6 to 20 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0062] Examples of the aryl group (Q-0) having one or more halogen atoms selected from a chlorine atom, a bromine atom, and an iodine atom as substituents include, among the aforementioned "aromatic hydrocarbon group in which some or all of the hydrogen atoms have been replaced with halogen atoms or heteroatom-containing groups," those in which at least one hydrogen atom has been replaced with a halogen atom, and at least one of the replaced halogen atoms is a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom.

[0063] Specific examples of the aryl group (Q-0) include a chlorophenyl group, a bromophenyl group, an iodophenyl group, a dichlorophenyl group, a dibromophenyl group, a diiodophenyl group, a trichlorophenyl group, a tribromophenyl group, a triiodophenyl group, a tetrachlorophenyl group, a tetrabromophenyl group, a tetraiodophenyl group, a pentachlorophenyl group, a pentabromophenyl group, a pentaiodophenyl group, a chlorotetrafluorophenyl group, a bromotetrafluorophenyl group, an iodotetrafluorophenyl group, a dichlorotrifluorophenyl group, a dibromotrifluorophenyl group, a diiodotrifluorophenyl group, a chloronaphthyl group, a bromonaphthyl group, an iodonaphthyl group, an α-pa Examples of such groups include a β-chloronaphthyl group, a β-perchloronaphthyl group, a 3,5-bis(chlorotetrafluorophenyl)-2,4,6-trifluorophenyl group, a 3,5-bis(bromotetrafluorophenyl)-2,4,6-trifluorophenyl group, a 3,5-bis(iodotetrafluorophenyl)-2,4,6-trifluorophenyl group, a 3,5-bis(pentachlorophenyl)-2,4,6-trifluorophenyl group, a 4-(chlorotetrafluorophenyl)-2,3,5,6-tetrafluorophenyl group, a 4-(bromotetrafluorophenyl)-2,3,5,6-tetrafluorophenyl group, and a 4-(iodotetrafluorophenyl)-2,3,5,6-tetrafluorophenyl group.

[0064] In compound (A), at least one of the aryl groups (Q-0) is preferably an aryl group (Q-1) represented by the following general formula (Q-1), more preferably each of the aryl groups (Q-0) is independently the aryl group (Q-1), and further preferably each of the aryl groups (Q-0) is the same aryl group (Q-1).

[0065] [ka]

[0066] In the general formula (Q-1), * represents [MQ4] -The bond to atom M of a group 13 element in the molecule is shown. In the general formula (Q-1), a plurality of X a are independently halogen atoms selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and two X's located at meta positions (3- or 5-positions) with respect to the bond to M; a At least one of the groups is a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom.

[0067] Specific examples of the aryl group (Q-1) include a chlorotetrafluorophenyl group, a bromotetrafluorophenyl group, an iodotetrafluorophenyl group, a dichlorotrifluorophenyl group, a dibromotrifluorophenyl group, a diiodotrifluorophenyl group, a trichlorodifluorophenyl group, a tribromodifluorophenyl group, a triiododifluorophenyl group, a tetrachlorofluorophenyl group, a tetrabromofluorophenyl group, a tetraiodofluorophenyl group, a pentachlorophenyl group, a pentabromophenyl group, a pentaiodophenyl group, a chlorobromotrifluorophenyl group, a chloroiodotrifluorophenyl group, a bromoiodotrifluorophenyl group, and a chlorobromoiododifluorophenyl group.

[0068] The aryl group represented by the general formula (Q-1) is preferably an aryl group represented by the following general formula (Q-1a) or (Q-1b).

[0069] [ka]

[0070] In the general formulas (Q-1a) and (Q-1b), * represents [MQ4] - The bond to atom M of a group 13 element in the m are independently a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom.

[0071] Specific examples of the aryl group represented by general formula (Q-1a) or (Q-1b) include a 3-chlorotetrafluorophenyl group, a 3-bromotetrafluorophenyl group, a 3-iodotetrafluorophenyl group, a 3,5-dichloro-2,4,6-trifluoro group, a 3,5-dibromo-2,4,6-trifluoro group, a 3,5-diiodo-2,4,6-trifluoro group, a 3-chloro-5-bromo-2,4,6-trifluorophenyl group, a 3-chloro-5-iodo-2,4,6-trifluorophenyl group, and a 3-bromo-5-iodo-2,4,6-trifluorophenyl group.

[0072] As the aryl group represented by the general formula (Q-1), in the general formulas (Q-1a) and (Q-1b), X m is a chlorine atom.

[0073] <Example of anion (β-1)> Specific examples of the anion (β-1) include tetrakis(3-chlorotetrafluorophenyl)borate ion, tetrakis(3-bromotetrafluorophenyl)borate ion, tetrakis(3-iodotetrafluorophenyl)borate ion, tetrakis(3,5-dichloro-2,4,6-trifluorophenyl)borate ion, tetrakis(3,5-dibromo-2,4,6-trifluorophenyl)borate ion, tetrakis(3,5-diiodo-2,4,6-trifluorophenyl)borate ion, tris(pentafluorophenyl)(pentachlorophenyl)borate ion, tris(3,5-dichloro-2,4,6-trifluorophenyl)(pentafluorophenyl)borate ion, tris(3,5-dichloro-2,4,6-trifluorophenyl)(α-perfluoronaphthyl)borate ion, bis(3,5-dibromo-2,4,6-trifluorophenyl)bis(pentafluorophenyl)borate ion, tris(pentafluorophenyl)(pentachlorophenyl)borate ion, tris(pentafluorophenyl)(α-perfluoronaphthyl)borate ion, bis(pentafluorophenyl)bis(pentafluorophenyl)borate ion, tris(pentafluorophenyl) ... Tris(3,5-dichloro-2,4,6-trifluorophenyl)(3,5-bis(pentafluorophenyl)borate ion, bis(3,5-dibromo-2,4,6-trifluorophenyl)bis(pentafluorophenyl)borate ion, tris(3,5-dichloro-2,4,6-trifluorophenyl)(4-trimethylsilylphenyl)borate ion, tris(3,5-dichloro-2,4,6-trifluorophenyl)(hydroxyphenyl)borate ion, Examples include tris(3,5-dichloro-2,4,6-trifluorophenyl)(4-(4'-hydroxyphenyl)phenyl)borate ion, tris(3,5-dichloro-2,4,6-trifluorophenyl)(6-hydroxy-2-naphthyl)borate ion, tris(3,5-dichloro-2,4,6-trifluoro)(4-hydroxyphenylphenyl)borate ion, and anions in which the boron atom in these anions is replaced with an atom of one of the other Group 13 elements mentioned above. Among these, tetrakis(3,5-dichloro-2,4,6-trifluorophenyl)borate ion is preferred.

[0074] [Anion (β-2) other than anion (β-1)] Examples of the anion (β-2) include anions other than the anion (β-1), namely, a tetrakispentafluorophenylborate ion, a tetrakis(α-perfluoronaphthylborate)borate ion, a tetrakis(β-perfluoronaphthylborate)borate ion, a carboxylate ion, a benzoate ion, an amide, a sulfate ester ion, a sulfonate ion, a hexafluorophosphate ion, a phosphate ester ion, a phosphonate ion, a fluoride ion, a chloride ion, a bromide ion, and an iodide ion, and the tetrakispentafluorophenylborate ion, the hexafluorophosphate ion, and the chloride ion are preferred.

[0075] <Specific Examples of Group 13 Element-Containing Compound (A)> Specific examples of the compound (A) include compounds represented by the following formulas (A-1) to (A-6).

[0076] [ka]

[0077] [ka]

[0078] The compound represented by formula (A-5) has two anions (β) (one anion (β-1) and one anion (β-2) (chloride ion)), and the total valence thereof is 2. The compound represented by formula (A-6) has three anions (β) (one anion (β-1) and two anions (β-2) (tetrakispentafluorophenylborate ion and hexafluorophosphate ion), and the total valence thereof is 3.

[0079] <Method for producing Group 13 element-containing compound (A)> Examples of methods for producing compound (A) include methods using the methods described in U.S. Patent Application Publication No. 2019 / 0330392, U.S. Patent No. 5,493,056, and European Patent No. 0426637. Specifically, compound (A) can be mainly produced by the following method.

[0080] The cation [α] γ+ Compounds containing ([α] γ+ Hydrochloride salts, including [α] γ+ and the anion {β} γ- By mixing the compound (A) with a salt containing the Group 13 element (lithium borate salt, sodium aluminate salt, etc.) in a solvent (cyclohexane, dichloromethane, methylcyclohexane, etc.), the target Group 13 element-containing compound and a by-product alkali metal chloride can be synthesized, and the latter can be removed by filtration to isolate compound (A).

[0081] The cation [α] γ+ The compound containing [(R 1 )3NH] + The hydrochloride salt is synthesized by dissolving the amine, which has a structure in which one proton has been removed from , in a solvent (dichloromethane, diethyl ether, hexane, cyclohexane, methylcyclohexane, toluene, etc.) and adding one or more equivalents of hydrogen chloride. The resulting hydrochloride salt is isolated by filtration.

[0082] <Uses of Group 13 element-containing compound (A)> Compound (A) is useful as a co-catalyst in an olefin polymerization catalyst. There are no particular limitations on the application of compound (A) as a co-catalyst as long as the catalyst is used for olefin polymerization. For example, it can be applied to a process of polymerizing olefins (such as ethylene and α-olefins having 3 to 20 carbon atoms) in the presence of an olefin polymerization catalyst. Here, "polymerization" is a general term for homopolymerization and copolymerization.

[0083] The phrase "polymerizing an olefin in the presence of an olefin polymerization catalyst" refers to, for example, adding the compound (A), the transition metal complex (B) used in the olefin polymerization catalyst, and any other components used in the olefin polymerization catalyst to a polymerization vessel in any order to polymerize the olefin.

[0084] The polymerization is not particularly limited as long as it is olefin polymerization, and can be carried out by either a liquid phase polymerization method such as solution polymerization or suspension polymerization, or a gas phase polymerization method, and the reaction conditions for each type of polymerization are not particularly limited.

[0085] When compound (A) is brought into contact with transition metal complex (B), the cations constituting compound (A) activate the transition metal complex (B), which is the main catalyst, and the amine moiety (or carbenium moiety) coordinates with the polymerization active species, thereby immobilizing the transition metal complex (B) on compound (A).

[0086] In the production of olefin polymers by polymerizing olefins in the presence of an olefin polymerization catalyst obtained by contacting a transition metal complex with a Group 13 element-containing compound, when compound (A) is used as the Group 13 element-containing compound, the size of the substituent in the anion moiety is larger than that of conventional Group 13 element-containing compounds (e.g., Group 13 element-containing compound (A'-1) described below). In particular, the introduction of a large-sized substituent at the meta position has the effect of lengthening the interionic distance in the ion pair consisting of the cation of the transition metal complex and the anion (β-1), and this correspondingly weakens the interionic interaction, which is thought to improve catalytic performance. [Example]

[0087] The present invention will be explained in more detail below based on examples, but the present invention is not limited to these examples.

[0088] <Measurement method> [Identification of Group 13 element-containing compound (A)] The structure of the group 13 element-containing compound is 270MHz 1H-NMR (GSH-270 manufactured by JEOL Ltd.), 160MHz 11 Measurement was carried out using B-NMR (ECA-500 manufactured by JEOL Ltd.) and the like, and various signals were assigned and determined according to standard methods.

[0089] [Polymer weight average molecular weight (Mw), molecular weight distribution (Mw / Mn)] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the olefin polymer were determined by gel permeation chromatography (GPC) using a Waters Alliance GPC 2000 gel permeation chromatograph (high-temperature size exclusion chromatograph) under the following operating conditions: (Operating conditions) Measurement equipment: Gel permeation chromatograph Alliance GPC2000 (Waters) Analysis software: Chromatography Data System Empower (trademark, manufactured by Waters) Column: TSKgel GMH6-HT x 2 + TSKgel GMH6-HT x 2 (inner diameter 7.5 mm x length 30 cm, manufactured by Tosoh Corporation) Mobile phase: o-dichlorobenzene (special grade, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) Detector: Differential refractometer (built into the device) Column temperature: 140℃ Flow rate: 1.0mL / min Injection volume: 400μL Sampling time interval: 1 second Sample concentration: 0.15% (w / v) Molecular weight calibration: Monodisperse polystyrene (manufactured by Tosoh Corporation) / molecular weight 495 to 20.6 million

[0090] <Synthesis of Group 13 element-containing compounds> [Manufacturing Example 1] (Synthesis of anion precursor (compound (a-1))) In Production Example 1 and Example 1, triphenylmethyl chloride was purchased from Fujifilm Wako Pure Chemical Industries, Ltd., 1-bromo-3,5-dichloro-2,4,6-trifluorobenzene was purchased from Matrix Scientific, Inc., 1.6 M n-butyllithium / hexane solution was purchased from Kanto Chemical Co., Inc., and 1.0 M boron tribromide / heptane solution was purchased from Aldrich, and all of these were used as they were. A 200 mL reactor was thoroughly dried and purged with nitrogen, and 2.0 g of 1-bromo-3,5-dichloro-2,4,6-trifluorobenzene and 30 mL of diethyl ether were added and stirred. The mixture was then cooled to -78°C, and 4.5 mL (1.0 equivalent) of a 1.6 M n-butyllithium / hexane solution was slowly added dropwise, followed by stirring for 1 hour. 2.1 mL (0.25 equivalent) of a 1.0 M boron tribromide / heptane solution was slowly added dropwise, and the mixture was stirred overnight while slowly warming to room temperature. The diethyl ether was then removed under reduced pressure, and the resulting suspension was dissolved in 10 mL of dichloromethane. The insoluble matter in the resulting suspension was removed by passing it through Celite on a glass filter, and the solvent was distilled off. The residue was washed with hexane, filtered, and dried under reduced pressure to obtain 600 mg (41% yield) of compound (a-1) represented by the following formula (a-1). 11 B-NMR(CDCl3)δ -16.79 ppm

[0091] [ka]

[0092] [Example 1] (Synthesis of Group 13 element-containing compound (A-1)) A 50 mL reactor that had been thoroughly dried and purged with nitrogen was charged with 240 mg of compound (a-1) obtained in Preparation Example 1 and 20 mL of dichloromethane and stirred. The mixture was then cooled in an ice bath, and a solution of 120 mg (1.5 equivalents) of triphenylmethyl chloride dissolved in 10 mL of dichloromethane was added dropwise. The mixture was stirred overnight while slowly warming to room temperature. The insoluble matter in the resulting suspension was then removed by passing it through Celite on a glass filter, and the solvent was distilled off. The residue was washed with a dichloromethane / hexane (1:1) mixed solvent and then with hexane, and dried under reduced pressure to obtain 150 mg (50% yield) of Group 13 element-containing compound (A-1) represented by the following formula (A-1). 1 H-NMR(tol-d8)δ 7.62(6H),7.82(6H),8.22(3H)ppm

[0093] [ka]

[0094] [Manufacturing Example 2] (Synthesis of cation precursor (compound (a-2))) In Production Example 2, N,N-dimethylaniline and hydrogen chloride (approximately 1 mol / L diethyl ether solution) were purchased from Tokyo Chemical Industry Co., Ltd. and used as they were. In a thoroughly dried, nitrogen-purged 50 mL reactor, 3.4 g of N,N-dimethylaniline and 10 mL of diethyl ether were added and stirred. Then, 25 mL of a 1 M hydrogen chloride / diethyl ether solution was added dropwise in an ice bath, and the mixture was allowed to warm to room temperature and stirred for 1 hour. The insoluble matter in the resulting suspension was collected by filtration and dried under reduced pressure to obtain 2.6 g (yield 99%) of compound (a-2) represented by the following formula (a-2). 1 H-NMR(CDCl3)δ 3.17(6H),7.47-7.49(3H),7.76-7.79(2H),14.51(NH)ppm

[0095] [ka]

[0096] [Example 2] (Synthesis of Group 13 element-containing compound (A-2)) A 50 mL reactor that had been thoroughly dried and purged with nitrogen was charged with 180 mg of compound (a-1) obtained in Preparation Example 1 and 10 mL of dichloromethane and stirred. A solution of 35 mg (1.0 equivalent) of compound (a-2) obtained in Preparation Example 2 dissolved in 10 mL of dichloromethane was added dropwise and stirred overnight at room temperature. The insoluble matter in the resulting suspension was then removed by passing it through Celite on a glass filter, and the solvent was distilled off. The residue was washed with water and then hexane and dried under reduced pressure to obtain 150 mg (71% yield) of the Group 13 element-containing compound (A-2) represented by the following formula (A-2). 1 H-NMR(tol-d8)δ 2.22(6H),6.51(2H),6.75(1H),7.01(2H)ppm

[0097] [ka]

[0098] [Example 3] (Synthesis of Group 13 Element-Containing Compound (A-5)) In Example 3 and Comparative Example 1, 1,4-diazabicyclo[2.2.2]octane dihydrochloride was purchased from Fujifilm Wako Pure Chemical Industries, Ltd. and used as is. A 50 mL reactor that had been thoroughly dried and purged with nitrogen was charged with 220 mg of compound (a-1) obtained in Preparation Example 1 and 5 mL of dichloromethane and stirred. Subsequently, a solution of 50 mg (1.0 equivalent) of 1,4-diazabicyclo[2.2.2]octane dihydrochloride in 10 mL of dichloromethane was added dropwise, and stirring was continued at room temperature for 24 hours. The insoluble matter in the resulting suspension was removed by passing it through Celite on a glass filter, and the solvent was distilled off. The residue was washed with water, hexane, and dichloromethane, respectively, and the insoluble matter was collected by filtration and dried under reduced pressure to obtain 160 mg (63% yield) of a Group 13 element-containing compound represented by the following formula (A-5). 1H NMR(CD3OD) δ 3.31(12H,s)ppm

[0099] [ka]

[0100] [Comparative Example 1] (Synthesis of Group 13 Element-Containing Compound (A'-5)) In Comparative Example 1, the lithium tetrakis(pentafluorophenyl)borate ethyl ether complex was purchased from Tokyo Chemical Industry Co., Ltd. and used as it was. A 200 mL reactor was thoroughly dried and purged with nitrogen, and 2.7 g of lithium tetrakis(pentafluorophenyl)borate ethyl ether complex and 80 mL of dichloromethane were added and stirred. A solution of 0.5 g of 1,4-diazabicyclo[2.2.2]octane dihydrochloride in 20 mL of dichloromethane was then added dropwise, and the mixture was stirred at room temperature for 24 hours. The insoluble material in the resulting suspension was removed by passing it through Celite on a glass filter, and the solvent was evaporated. The residue was washed with water, hexane, and dichloromethane, respectively. The insoluble material was collected by filtration and dried under reduced pressure, yielding 1.9 g (85% yield) of a Group 13 element-containing compound represented by the following formula (A'-5). 1 H NMR(CD3OD) δ 3.34(12H,s)ppm

[0101] [ka]

[0102] <Polymerization evaluation> In order to evaluate the Group 13 element-containing compounds synthesized or purchased in the above Examples or Comparative Examples as cocatalysts in olefin polymerization catalysts, the following olefin polymerizations were carried out and the polymerization activities were compared.

[0103] The Group 13 element-containing compounds (A'-1), (A'-2), and (A'-5) used in the polymerization comparative examples are as follows. ·Compounds containing Group 13 elements (A'-1) Triphenylcarbenium tetrakis(pentafluorophenyl)borate represented by the following formula (A'-1) was purchased from Tokyo Chemical Industry Co., Ltd. and used as is.

[0104] [ka]

[0105] ·Compounds containing Group 13 elements (A'-2) N,N-dimethylanilinium tetrakis(pentafluorophenyl)borate represented by the following formula (A'-2) was purchased from Tokyo Chemical Industry Co., Ltd. and used as is.

[0106] [ka]

[0107] ·Compounds containing Group 13 elements (A'-5) The compound represented by the formula (A'-5) obtained in Comparative Example 1 was used.

[0108] As the transition metal complex (B), a transition metal complex (B2-1) represented by the following formula (B2-1) produced by a conventionally known method was used.

[0109] [ka]

[0110] [Polymerization Example 1] 250 mL of toluene was added to a 500 mL glass reactor thoroughly purged with nitrogen. Ethylene was then supplied at 100 L / hr to saturate the reactor with ethylene. Polymerization was then initiated by adding 0.20 mmol of triisobutylaluminum, 0.500 μmol of the transition metal complex (B2-1), and 4 equivalents (2.000 μmol) of the Group 13 element-containing compound (A-1) obtained in Example 1 relative to the transition metal complex (B2-1). Ethylene was continuously supplied at 100 L / hr, and polymerization was carried out at 50°C under atmospheric pressure for 5 minutes. The polymerization was then terminated by adding a small amount of methanol. After polymerization, the reaction mixture was added to 1 L of methanol containing a small amount of hydrochloric acid to precipitate an olefin polymer. The resulting olefin polymer had an Mw of 228,000 and an Mw / Mn ratio of 4.5.

[0111] [Polymerization Example 2] Polymerization was carried out in the same manner as in Polymerization Example 1, except that the Group 13 element-containing compound (A-2) obtained in Example 2 was used instead of the Group 13 element-containing compound (A-1), to obtain 1.56 g of an olefin polymer. The Mw of the obtained olefin polymer was 214,000, and the Mw / Mn was 3.5.

[0112] [Polymerization Example 3] Polymerization was carried out in the same manner as in Polymerization Example 1, except that the Group 13 element-containing compound (A-5) obtained in Example 3 was used instead of the Group 13 element-containing compound (A-1), to obtain 1.58 g of an olefin polymer. The Mw of the obtained olefin polymer was 166,000, and the Mw / Mn was 3.6.

[0113] [Comparative Polymerization Example 1] Polymerization was carried out in the same manner as in Polymerization Example 1, except that the Group 13 element-containing compound (A'-1) was used instead of the Group 13 element-containing compound (A-1), to obtain 1.48 g of an olefin polymer. The Mw of the obtained olefin polymer was 106,000, and the Mw / Mn was 4.5.

[0114] [Comparative Polymerization Example 2] Polymerization was carried out in the same manner as in Polymerization Example 1, except that the Group 13 element-containing compound (A'-2) was used instead of the Group 13 element-containing compound (A-1), to obtain 1.04 g of an olefin polymer. The Mw of the obtained olefin polymer was 93,100, and the Mw / Mn was 3.4.

[0115] [Comparative Polymerization Example 3] Polymerization was carried out in the same manner as in Polymerization Example 1, except that the Group 13 element-containing compound (A'-5) obtained in Comparative Example 1 was used instead of the Group 13 element-containing compound (A-1), to obtain 1.34 g of an olefin polymer. The Mw of the obtained olefin polymer was 103,000, and the Mw / Mn was 3.2.

[0116] In the polymerization examples using the Group 13 element-containing compound (A) of the present invention, more olefin polymers were obtained than in the polymerization comparison examples, which shows that the olefin polymerization catalyst using the Group 13 element-containing compound (A) as a co-catalyst exhibits high polymerization activity.

Claims

1. A compound (A) containing a Group 13 element represented by the following general formula (A): [a] γ＋ {b} γ－ …(A) [In the general formula (A), γ is an integer of 1 to 2.] [α] γ＋ is a cation represented by the following general formula (α-1), (α-2) or (α-3). [(R １ ) ３ NH] ＋ …(α-1) [(R) ２ ) ３ C] ＋ …(a-2) [(R) ３ ) ３ N-R ４ -N (R) ３ ) ３ ] γ＋ …(a-3) (In general formulas (α-1), (α-2) and (α-3), a plurality of R １ , R ２ , and R ３ are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 30 carbon atoms, or an aromatic substituent having 6 to 30 carbon atoms, and a plurality of R ３ may be bonded to each other to form a ring represented by the following general formula (a-5): ４ is a methylene group, a linear or branched alkylene group having 2 to 30 carbon atoms, a group in which some or all of the carbon-carbon single bonds in the alkylene group have been replaced with double bonds, an alicyclic hydrocarbon group having 3 to 30 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms. {β} γ－ represents one or more anions (β), the total valence of said anions (β) being γ. The anion (β) is an anion (β-1) represented by the following general formula (β-1) or an anion (β-2) other than the above (β-1). [MQM ４ ] － …(b-1) (In general formula (β-1), M is an atom of a Group 13 element. All four Qs are independently an aryl group represented by the following general formula (Q-1a) or (Q-1b): At least one of the anions (β) is the anion (β-1). When a plurality of anions (β) are present, they may be the same or different. 【Chemistry 1】 [In general formula (a-5), * represents R in general formula (α-3)] ４ indicates a bond to R ３ has the same meaning as the same symbol in the general formula (α-3). In the general formulae (Q-1a) and (Q-1b), * represents a bond to the M, and a plurality of X ｍ are independently a halogen atom selected from a chlorine atom, a bromine atom, and an iodine atom.

2. The Group 13 element-containing compound (A) according to claim 1 , wherein in the general formula (A), M is a boron atom.

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