JP2007084790A - Ring-closing polymerization of diene - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a polymer having a polar group and excellent in heat resistance and to provide a method for producing the polymer. <P>SOLUTION: The polymer is represented by formula (1) (wherein X<SP>1</SP>, X<SP>2</SP>, X<SP>3</SP>and X<SP>4</SP>are each an atom of XVI group of the periodic table of element; R<SP>1</SP>and R<SP>2</SP>are each a hydrogen atom or a hydrocarbon group; A<SP>1</SP>, A<SP>2</SP>, A<SP>3</SP>, A<SP>4</SP>, A<SP>5</SP>, A<SP>6</SP>, A<SP>7</SP>, A<SP>8</SP>, A<SP>9</SP>and A<SP>10</SP>are each a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, a substituted silyl group, an alkoxy group, an aralkyloxy group, an aryloxy group, a di-substituted amino group or a hydrocarbon thio group). <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a polymer having a polar group and excellent heat resistance and a method for producing the same.

  It is known that by introducing a polar group into the polymer, various properties derived from the compatibility of the polar group can be imparted to the polymer. Among them, as a polymer having higher heat resistance, for example, Patent Document 1 discloses a norbornene monomer having a hydroxyl group or a hydrocarboxy group and a norbornene monomer having an unsubstituted tricyclic or higher structure. , Hydrogenated ring-opening metathesis copolymers obtained by ring-opening metathesis copolymerization are described.

JP 2002-363263 A

However, the ring-opening metathesis copolymer hydride described in Patent Document 1 cannot always be said to have sufficient heat resistance. In addition, in the production method, when producing a monomer having a polar group by (co) polymerization, depending on the combination of the monomer and the polymerization catalyst, the polymerization catalyst is poisoned by the polar group, and the polymerization activity The polymerization reaction did not proceed or sufficient activity could not be obtained. Therefore, for example, as in the production method described in Patent Document 1, it must be based on ring-opening metathesis (co) polymerization using a polymerization catalyst mainly composed of an organic ruthenium compound, and in this case, a hydrogenation step is further required. Met.
Under such circumstances, the problem to be solved by the present invention, that is, an object of the present invention is to provide a polymer having a polar group and excellent in heat resistance and a method for producing the same.

（ただし、上式（１）において、Ｘ¹、Ｘ²、Ｘ³およびＸ⁴はそれぞれ独立に、元素の周期表第１６族の原子を表し、Ｒ¹およびＲ²はそれぞれ独立に、水素原子または炭素原子数１〜２０の炭化水素基を表し、Ｒ¹とＲ²は互いに結合していてもよい。Ａ¹、Ａ²、Ａ³、Ａ⁴、Ａ⁵、Ａ⁶、Ａ⁷、Ａ⁸、Ａ⁹およびＡ¹⁰はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、２置換アミノ基、または炭化水素チオ基を表す。） The present invention is a polymer comprising a repeating unit represented by the following formula (1).

(However, in the above formula (1), X ¹ , X ² , X ³ and X ⁴ each independently represent an atom of Group 16 of the periodic table of elements, and R ¹ and R ² each independently represent a hydrogen atom. Alternatively, it represents a hydrocarbon group having 1 to 20 carbon atoms, and R ¹ and R ² may be bonded to each other: A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ and A ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, disubstituted amino group, or hydrocarbon Represents a thio group.)

（ただし、上式（３）において、Ｘ¹、Ｘ²、Ｘ³およびＸ⁴はそれぞれ独立に、元素の周期表第１６族の原子を表し、Ｒ¹およびＲ²はそれぞれ独立に、水素原子または炭素原子数１〜２０の炭化水素基を表し、Ｒ¹とＲ²は互いに結合していてもよい。Ａ¹、Ａ²、Ａ³、Ａ⁴、Ａ⁵、Ａ⁶、Ａ⁷、Ａ⁸、Ａ⁹およびＡ¹⁰はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、２置換アミノ基、または炭化水素チオ基を表す。） The present invention is also a method for producing a polymer comprising a repeating unit represented by the above formula (1), which comprises a step of polymerizing a compound represented by the following formula (3).

(However, in the above formula (3), X ¹ , X ² , X ³ and X ⁴ each independently represent an atom of Group 16 of the periodic table of the elements, and R ¹ and R ² each independently represent a hydrogen atom. Alternatively, it represents a hydrocarbon group having 1 to 20 carbon atoms, and R ¹ and R ² may be bonded to each other: A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ and A ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, disubstituted amino group, or hydrocarbon Represents a thio group.)

  ADVANTAGE OF THE INVENTION According to this invention, the polymer excellent in heat resistance which has a polar group, and its manufacturing method are provided.

Examples of X ¹ , X ² , X ³ and X ^{4 in} formula (1) include an oxygen atom, a sulfur atom and a selenium atom. Among these, an oxygen atom is preferable.

As the hydrocarbon group for R ¹ and R ² in the formula (1), a linear alkyl group such as a methyl group, an ethyl group and an n-butyl group; an isopropyl group, an isobutyl group, a tert-butyl group and a neopentyl group Examples of such branched alkyl groups include cyclic alkyl groups such as cyclohexyl and cyclooctyl groups. R ¹ and R ² are preferably an alkyl group having 1 to 20 carbon atoms, more preferably a linear unsubstituted alkyl group having 1 to 10 carbon atoms, and further preferably a methyl group or an ethyl group. Or an n-butyl group.

When R ¹ and R ² in the formula (1) are bonded to each other, examples of the ring formed by the bond include an aliphatic ring and an aromatic ring. These rings may have a substituent. As the divalent group formed by the bond between R ¹ and R ² in the aliphatic ring, methylene group, isopropylidene group, 1,2-ethylene group, 1,2-cyclohexylene group, 1,3 -Cyclohexylene group, 1,4-cyclohexylene group, 1,2-norbornene group, 2,3-butene group, 2,3-dimethyl-2,3-butene group, and 2,4-pentene group be able to. Of these, a methylene group, an isopropylidene group, a 2,3-butene group, or a 2,3-dimethyl-2,3-butene group is preferable. As the divalent group formed by the bond between R ¹ and R ² in the aromatic ring, 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 1,2-naphthylene Group, 1,3-naphthylene group, 1,4-naphthylene group, 1,5-naphthylene group, 1,6-naphthylene group, 1,7-naphthylene group, 1,8-naphthylene group, 2,3-naphthylene group 2,4-naphthylene group, 2,5-naphthylene group, 2,6-naphthylene group, 2,7-naphthylene group, 2,8-naphthylene group, 2,2′-biphenylene group, 1,2-dimethylene Examples include phenyl group, 1,3-dimethylenephenyl group, 1,4-dimethylenephenyl group, 1,2-dimethylenephenyl group, 1,3-diethylenephenyl group, and 1,4-diethylenephenyl group. it can.

As the halogen atom in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ in the formula (1), a fluorine atom, a chlorine atom, a bromine atom, And iodine atom. Among them, preferred is a fluorine atom.

As the alkyl group in ^{A 1, A 2, A 3} , A 4, A 5, A 6, A 7, A 8, A 9, and A ¹⁰ in Formula (1), a methyl group, an ethyl group, and n- butyl Illustrate linear alkyl groups such as groups; branched alkyl groups such as isopropyl, isobutyl, tert-butyl, and neopentyl groups; and cyclic alkyl groups such as cyclohexyl and cyclooctyl groups Can do.

As an aralkyl group in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ in the formula (1), a benzyl group, a phenethyl group, 2-methyl Examples include benzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2,6-dimethylbenzyl group, and 3,5-dimethylbenzyl group. The aralkyl group may have a substituent such as a halogen atom, a hydrocarbon oxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

As the aryl group in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ in the formula (1), a phenyl group, a tolyl group, and a mesityl group Can be illustrated. The aryl group may have a substituent such as a halogen atom, a hydrocarbon oxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

As substituted silyl groups in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ in the above formula (1), a trimethylsilyl group, a diethylmethylsilyl group , Ethyldimethylsilyl group, and triethylsilyl group. The substituted silyl group may have a substituent such as a halogen atom, a hydrocarbon oxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

The alkoxy groups in ^{A 1, A 2, A 3} , A 4, A 5, A 6, A 7, A 8, A 9, and A ¹⁰ in Formula (1), a methoxy group, Etokishiki group and n- butoxy Linear alkoxy groups such as groups; branched alkoxy groups such as isopropoxy groups, isobutoxy groups, tert-butoxy groups, and neopentoxy groups; and cyclic alkoxy groups such as cyclohexyloxy groups and cyclooctyloxy groups. It can be illustrated. The alkoxy group may have a substituent such as a halogen atom, a hydrocarbon oxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

As the aralkyloxy group in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ in the formula (1), a benzyloxy group, a phenethyloxy group, 2- Examples thereof include a methylbenzyloxy group, a 3-methylbenzyloxy group, a 4-methylbenzyloxy group, a 2,6-dimethylbenzyloxy group, and a 3,5-dimethylbenzyloxy group. The aralkyloxy group may have a substituent such as a halogen atom, a hydrocarbon oxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

As an aryloxy group in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ in the formula (1), a phenoxy group, a 2-methylphenoxy group 2-ethylphenoxy group, 2-n-propylphenoxy group, 2-isopropylphenoxy group, 2-n-butylphenoxy group, 2-isobutylphenoxy group, 2-tert-butylphenoxy group, 3-methylphenoxy group, 3 -Isopropylphenoxy group, 3-n-butylphenoxy group, 3-tert-butylphenoxy group, 4-methylphenoxy group, 4-isopropylphenoxy group, 4-n-butylphenoxy group, 4-tert-butylphenoxy group, 2 , 3-dimethylphenoxy group, 2,4-dimethylphenoxy group, 2,5-dimethylphenoxy group, 2,6-dimethylphenoxy group Group, 3,5-dimethylphenoxy group, 2,6-diisopropyl-phenoxy group, can be exemplified 2,6-di -tert- butyl phenoxy group, and a naphthoxy group. The aryloxy group may have a substituent such as a halogen atom, a hydrocarbon oxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

As a disubstituted amino group in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ in the formula (1), an N, N-dimethylamino group , N, N-diethylamino group, and linear alkylamino groups such as N, N-di-n-butylamino group; N, N-diisopropylamino group, N, N-diisobutylamino group, N, N- Branched alkylamino groups such as di-tert-butylamino group and N, N-dineopentylamino group; and cyclic groups such as N, N-dicyclohexylamino group and N, N-dicyclooctylamino group An alkylamino group can be exemplified.

The hydrocarbon thio groups in A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ and A ¹⁰ in the formula (1) are methylthio, ethylthio and n- Linear alkylthio groups such as butylthio groups; branched alkylthio groups such as isopropylthio groups, isobutylthio groups, tert-butylthio groups, and neopentylthio groups; and cyclohexylthio groups and cyclooctylthio groups Among the cyclic alkylthio groups, A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ , and A ¹⁰ may be a hydrogen atom, a halogen atom, or An alkyl group having 1 to 10 carbon atoms is preferable, a hydrogen atom or a methyl group is more preferable, and a hydrogen atom is further preferable.

A ⁵ and A ⁶ or A ⁷ and A ⁸ may be bonded to each other. Examples of the ring formed by these bonds include aliphatic rings such as cyclobutane, cyclopentane and cyclohexane, and aromatic rings. These rings may have a substituent.

（ただし、上式（２）において、Ｘ¹、Ｘ²、Ｘ³およびＸ⁴はそれぞれ独立に、元素の周期表第１６族の原子を表し、Ｒ¹およびＲ²はそれぞれ独立に、水素原子または炭素原子数１〜２０の炭化水素基を表し、Ｒ¹とＲ²は互いに結合していてもよい。Ａ¹、Ａ²、Ａ³、Ａ⁴、Ａ⁵、Ａ⁶、Ａ⁷、Ａ⁸、Ａ⁹およびＡ¹⁰はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、２置換アミノ基、または炭化水素チオ基を表す。） In the repeating unit represented by the formula (1), the steric positional relationship between the main chain of the polymer and the 5-membered ring is not particularly limited. From the viewpoint of a polymer having excellent heat resistance, the 5-membered ring is preferably a trans form represented by the following formula (2) with respect to the main chain.

(However, in the above formula (2), X ¹ , X ² , X ³ and X ⁴ each independently represent an atom of Group 16 of the periodic table of elements, and R ¹ and R ² each independently represent a hydrogen atom. Alternatively, it represents a hydrocarbon group having 1 to 20 carbon atoms, and R ¹ and R ² may be bonded to each other: A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ and A ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, disubstituted amino group, or hydrocarbon Represents a thio group.)

Said positional relationship is calculated | required by the < ¹³ > C-NMR spectrum using the deuterated chloroform solution of the polymer of this invention. In the spectrum, when the peak position of deuterated chloroform as a solvent is 77 ppm, the peak (i) appearing at 45 to 46 ppm is attributed to a carbon atom in which the 5-membered ring is in a trans form with respect to the main chain of the polymer. The peak (ii) appearing at 39-42 ppm is attributed to a carbon atom whose 5-membered ring is cis with respect to the main chain of the polymer.
Therefore, by determining the ratio of the area of peak (i) to the sum of the area of peak (i) and the area of peak (ii) [100 (i) / {(i) + (ii)}] The proportion of the shape is determined.

エリトロジアイソタクチック

エリトロジシンジオタクチック

トレオジアイソタクチック

トレオジシンジオタクチック
上式において、Ｃ¹は、式（１）で表される繰り返し単位中のＡ⁵およびＡ⁶が結合している炭素原子を表し、Ｃ²は、式（１）で表される繰り返し単位中のＡ⁷およびＡ⁸が結合している炭素原子を表し、Ｃ¹およびＣ²を結ぶ曲線は、Ａ⁵およびＡ⁶が結合している炭素原子とＡ⁷およびＡ⁸が結合している炭素原子の結合を表し、式（１）で表される繰り返し単位中の他の炭素原子および他の置換基は省略されている。 The stereoregularity of the polymer of the present invention is such that two asymmetric carbon atoms (A ⁹ and A ¹⁰ are bonded to each other in the main chain of the polymer composed of the repeating unit represented by the formula (1). Is determined by the absolute configuration of the carbon atom). The stereoregularity includes the following four types: erythro-isotactic, erythrosin-diotactic, throdi-isotactic, and throdi-syndiotactic. These four types of three-dimensional regularity, "Encyclopedia of Polymer Science and Engineering (Encyclopedia of polymer Science and Engineering)" (the United States), Second Edition (2 ^nd Ed.), Vol. 10, John・ John Wiley & Sons, 1987, p. 191-203).

Erythroisotactic

Erythrodysyndiotactic

Threodiisotactic

Threodisin ditactic In the above formula, C ¹ represents a carbon atom to which A ⁵ and A ⁶ in the repeating unit represented by formula (1) are bonded, and C ² is represented by formula (1). The carbon atom to which A ⁷ and A ⁸ in the repeating unit is bonded, and the curve connecting C ¹ and C ² is the carbon atom to which A ⁵ and A ⁶ are bonded to A ⁷ and A ^8. This represents a bond of bonded carbon atoms, and other carbon atoms and other substituents in the repeating unit represented by the formula (1) are omitted.

  The stereoregularity of the polymer of the present invention is not particularly limited, but from the viewpoint of producing a polymer excellent in heat resistance, preferably, erythroisotactic triad or throdiisotactic triad is more than 25%. A sotactic polymer or a dicindiotactic polymer having an erythrosindiotactic triad or throdisindiotactic triad greater than 25%.

  More preferably, the diisotactic polymer is a polymer having a diisotactic triad of 30% or more, and more preferably a polymer having a diisotactic triad of 50% or more. More preferable as the disyndiotactic polymer is a polymer having a disyndiotactic triad of 30% or more, and more preferable is a polymer having a disyndiotactic triad of 50% or more.

Said stereoregularity is calculated | required by the < ¹³ > C-NMR spectrum using the deuterated chloroform solution of the polymer of this invention. In the spectrum, when the peak position of deuterated chloroform as a solvent is 77 ppm, the peak (iii) appearing at 46.2 to 46.6 ppm is attributed to the carbon atom derived from the treodiisotactic triad, and 46.9 The peak (iv) appearing at ˜47.3 ppm is attributed to the carbon atom derived from the threodicindiotactic triad.
Therefore, the ratio of the area of peak (iii) to the total area of peaks (iii) and (iv) determines the throdiisotactic triad composition, while the area of peak (iv) and the total area The ratio determines the threodicindiotactic triad composition.

  As the compound represented by the formula (3), diallyl dicarboxylic acid ester can be exemplified. Among them, isopropylidene diallyl malonate, dimethyl diallyl malonate, diethyl diallyl malonate, diisopropyl diallyl malonate, or ditertiary butyl diallyl malonate are all known compounds. . Further, dipropyl diallyl malonic acid ester and dicyclohexyl diallyl malonic acid ester can be obtained by the method as shown in Examples.

  The polymer of the present invention is obtained by polymerizing a compound represented by the formula (3) in the presence of a polymerization catalyst produced by contacting a transition metal compound with an organoaluminum compound and / or a boron compound, Can be manufactured.

The transition metal compound is not particularly limited as long as it is a transition metal compound having addition polymerization activity, and may be a known transition metal compound. Among these, transition metal compounds having a transition metal atom of Group 4 to 10 of the periodic table of elements or a lanthanoid series transition metal atom are preferable. Examples of the transition metal compound include a transition metal compound represented by the following formula (4) and a μ-oxo type transition metal compound that is a dimer obtained by a reaction of the transition metal compound and water. .
L _a M ¹ X _b (4)
(In the above formula (4), M ¹ represents a group 4-10 transition metal atom or a lanthanoid series transition metal atom in the periodic table of elements (IUPAC 1985), and L represents a group having a cyclopentadiene-type anion skeleton. , Or a group containing a hetero atom, and when a plurality of L are present, they are directly connected to each other, or a carbon atom, a silicon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom X is a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, a is a number satisfying 0 <a ≦ 8, and b is 0 <b ≦ 8. Represents a number satisfying.)

M ¹ includes titanium atom, zirconium atom, hafnium atom, vanadium atom, niobium atom, tantalum atom, chromium atom, iron atom, ruthenium atom, cobalt atom, rhodium atom, nickel atom, palladium atom, samarium atom, and ytterbium atom. It can be illustrated.

  Examples of the group having a cyclopentadiene-type anion skeleton in L include a cyclopentadienyl group, a substituted cyclopentadienyl group, an indenyl group, a substituted indenyl group, a fluorenyl group, and a substituted fluorenyl group.

Specific examples of the group having a cyclopentadiene-type anion skeleton include η ⁵ -cyclopentadienyl group, η ⁵ -methylcyclopentadienyl group, η ⁵ -tert-butylcyclopentadienyl group, η ⁵ -1, 2-dimethylcyclopentadienyl group, η ⁵ -1,3-dimethylcyclopentadienyl group, η ⁵ -1-tert-butyl-2-methylcyclopentadienyl group, η ⁵ -1-tert-butyl- 3-methylcyclopentadienyl group, eta ^{5-1-methyl-2-isopropyl-cyclopentadienyl} group, eta ^{5-1-methyl-3-isopropyl-cyclopentadienyl} group, eta ^5-1,2,3 trimethyl cyclopentadienyl group, eta ^{5-1,2,4-trimethyl} cyclopentadienyl group, eta ⁵ - tetramethylcyclopentadienyl group, eta ⁵ - pentamethyl cyclo Ntajieniru group, eta ⁵ - indenyl group, eta ^{5-4,5,6,7-tetrahydroindenyl} group, eta ^{5-2-methylindenyl} group, eta ^{5-3-methylindenyl} group, eta ^5-4- Methyl indenyl group, η ⁵ -5-methyl indenyl group, η ⁵ -6-methyl indenyl group, η ⁵ -7-methyl indenyl group, η ⁵ -2-tert-butyl indenyl group, η ^5- 3-tert-butyl indenyl group, η ⁵ -4-tert-butyl indenyl group, η ⁵ -5-tert-butyl indenyl group, η ⁵ -6-tert-butyl indenyl group, η ⁵ -7- tert- butyl indenyl group, eta ^{5-2,3-dimethyl-indenyl} group, eta ^{5-4,7-dimethyl-indenyl} group, eta ^{5-2,4,7-trimethyl} indenyl group, eta ^5-2- methyl-4-isopropyl-indenyl group, eta ⁵ -4,5 Benzindenyl group, eta ^{5-2-methyl-4,5-benzindenyl} group, eta ^5-4-phenyl indenyl group, eta ^{5-2-methyl-5-phenyl} indenyl group, eta ^{5-2-methyl-4-} phenyl indenyl group, eta ^{5-2-methyl-4-naphthyl} indenyl group, eta ⁵ - fluorenyl group, eta ^{5-2,7-dimethyl} fluorenyl group, and eta ^5-2,7-di -tert- A butylfluorenyl group can be exemplified.

  Examples of the hetero atom related to the group containing a hetero atom in L include an oxygen atom, a sulfur atom, a nitrogen atom, and a phosphorus atom. Examples of the group include an alkoxy group, an aryloxy group, a thioalkoxy group, a thioaryloxy group, an alkylamino group, an arylamino group, an alkylphosphino group, an arylphosphino group, an oxygen atom, a sulfur atom, a nitrogen atom or a phosphorus atom. An aromatic or aliphatic heterocyclic group having a ring structure and a chelating ligand can be exemplified.

  Alkoxy groups such as methoxy group, ethoxy group, propoxy group, and butoxy group as a group containing a hetero atom; phenoxy group, 2-methylphenoxy group, 2,6-dimethylphenoxy group, 2,4,6-trimethyl Phenoxy group, 2-ethylphenoxy group, 4-n-propylphenoxy group, 2-isopropylphenoxy group, 2,6-diisopropylphenoxy group, 4-sec-butylphenoxy group, 4-tert-butylphenoxy group, 2,6 Aryloxy groups such as -di-sec-butylphenoxy, 2-tert-butyl-4-methylphenoxy, and 2,6-di-tert-butylphenoxy; 4-methoxyphenoxy, 2,6- Dimethoxyphenoxy group, 3,5-dimethoxyphenoxy group, 2-chlorophenoxy group 4-nitrosophenoxy group, 4-nitrophenoxy group, 2-aminophenoxy group, 3-aminophenoxy group, 4-aminothiophenoxy group, 2,3,6-trichlorophenoxy group, and 2,4,6-trifluoro Substituted aryloxy groups such as phenoxy groups; hydrocarbon thio groups such as thiomethoxy groups; alkyl-substituted amino groups such as dimethylamino groups, diethylamino groups, dipropylamino groups, isopropylamino groups, tert-butylamino groups, and Aryl substituted amino groups such as diphenylamino groups; pyrrolyl groups; phosphino groups such as dimethylphosphino groups; and 2- (2-oxy-1-propyl) phenoxy groups, catechol, resorcinol, 4-isopropylcatechol, 3 -Methoxycatechol, 1,8-dihydro Sinaphthyl group, 1,2-dihydroxynaphthyl group, 2,2′-biphenyldiol group, 1,1′-bi-2-naphthol group, 2,2′-dihydroxy-6,6′-dimethylbiphenyl group, 4 , 4 ′, 6,6′-tetra-tert-butyl-2,2′methylenediphenoxy group and 4,4 ′, 6,6′-tetramethyl-2,2′-isobutylidenediphenoxy group An aryldioxy group can be exemplified.

  The chelating ligand means a ligand having a plurality of binding sites. Examples of the ligand include acetylacetonate, diimine, oxazoline, bisoxazoline, terpyridine, acyl hydrazone, diethylenetriamine, triethylenetetramine, porphyrin, crown ether, and cryptate.

  When a plurality of L are present, groups having a cyclopentadiene-type anion skeleton, groups having a cyclopentadiene-type anion skeleton and a group containing a hetero atom, or groups containing a hetero atom are directly connected to each other. Or linked through a residue containing a carbon atom, a silicon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. Such residues include alkylene groups such as ethylene groups and propylene groups; substituted alkylene groups such as dimethylmethylene groups and diphenylmethylene groups; such as silylene groups, dimethylsilylene groups, diphenylsilylene groups, and tetramethyldisilylene groups. Substituted silylene groups; and heteroatoms such as nitrogen, oxygen, sulfur and phosphorus atoms can be exemplified.

  Examples of the halogen atom in X according to formula (4) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, and n- A propyl group, an isopropyl group, an n-butyl group, a phenyl group, and a benzyl group can be exemplified.

A and b in Formula (4) are appropriately selected so as to be neutral as a transition metal compound in consideration of the valence of the transition metal atom M ^{1 and} the valences of L and X.

As the transition metal compound represented by the formula (4) where M ¹ is a titanium atom, bis (cyclopentadienyl) titanium dichloride, bis (methylcyclopentadienyl) titanium dichloride, bis (n-butylcyclopentadidi) Enyl) titanium dichloride, bis (dimethylcyclopentadienyl) titanium dichloride, bis (ethylmethylcyclopentadienyl) titanium dichloride, bis (trimethylcyclopentadienyl) titanium dichloride, bis (tetramethylcyclopentadienyl) titanium dichloride Bis (pentamethylcyclopentadienyl) titanium dichloride, bis (indenyl) titanium dichloride, bis (4,5,6,7-tetrahydroindenyl) titanium dichloride, bis (fluorenyl) titanium dichloride, Pentadienyl (pentamethylcyclopentadienyl) titanium dichloride, cyclopentadienyl (indenyl) titanium dichloride, cyclopentadienyl (fluorenyl) titanium dichloride, indenyl (fluorenyl) titanium dichloride, pentamethylcyclopentadienyl (indenyl) titanium dichloride , Pentamethylcyclopentadienyl (fluorenyl) titanium dichloride,

Ethylenebis (cyclopentadienyl) titanium dichloride, ethylenebis (2-methylcyclopentadienyl) titanium dichloride, ethylenebis (3-methylcyclopentadienyl) titanium dichloride, ethylenebis (2-n-butylcyclopentadi) Enyl) titanium dichloride, ethylenebis (3-n-butylcyclopentadienyl) titanium dichloride, ethylenebis (2,3-dimethylcyclopentadienyl) titanium dichloride, ethylenebis (2,4-dimethylcyclopentadienyl) Titanium dichloride, ethylene bis (2,5-dimethylcyclopentadienyl) titanium dichloride, ethylene bis (3,4-dimethylcyclopentadienyl) titanium dichloride, ethylene bis (2,3-ethylmethylcyclopentadiene) L) Titanium dichloride, ethylene bis (2,4-ethylmethylcyclopentadienyl) titanium dichloride, ethylene bis (2,5-ethylmethylcyclopentadienyl) titanium dichloride, ethylene bis (3,5-ethylmethylcyclopenta) Dienyl) titanium dichloride, ethylenebis (2,3,4-trimethylcyclopentadienyl) titanium dichloride, ethylenebis (2,3,5-trimethylcyclopentadienyl) titanium dichloride, ethylenebis (tetramethylcyclopentadi) Enyl) titanium dichloride, ethylenebis (indenyl) titanium dichloride, ethylenebis (4,5,6,7-tetrahydroindenyl) titanium dichloride, ethylenebis (2-phenylindenyl) titanium dichloride, ethylenebi (2-methylindenyl) titanium dichloride, ethylenebis (2-methyl-4-phenylindenyl) titanium dichloride, ethylenebis (2-methyl-4-naphthylindenyl) titanium dichloride, ethylenebis (2-methyl-4) , 5-Benzoindenyl) titanium dichloride, ethylenebis (fluorenyl) titanium dichloride, ethylene (cyclopentadienyl) (pentamethylcyclopentadienyl) titanium dichloride, ethylene (cyclopentadienyl) (indenyl) titanium dichloride, ethylene (Methylcyclopentadienyl) (indenyl) titanium dichloride, ethylene (n-butylcyclopentadienyl) (indenyl) titanium dichloride, ethylene (tetramethylcyclopentadienyl) (indenyl) thi Tandichloride, ethylene (cyclopentadienyl) (fluorenyl) titanium dichloride, ethylene (methylcyclopentadienyl) (fluorenyl) titanium dichloride, ethylene (pentamethylcyclopentadienyl) (fluorenyl) titanium dichloride, ethylene (n-butyl) Cyclopentadienyl) (fluorenyl) titanium dichloride, ethylene (tetramethylpentadienyl) (fluorenyl) titanium dichloride, ethylene (indenyl) (fluorenyl) titanium dichloride,

Isopropylidenebis (cyclopentadienyl) titanium dichloride, isopropylidenebis (2-methylcyclopentadienyl) titanium dichloride, isopropylidenebis (3-methylcyclopentadienyl) titanium dichloride, isopropylidenebis (2-n- Butylcyclopentadienyl) titanium dichloride, isopropylidenebis (3-n-butylcyclopentadienyl) titanium dichloride, isopropylidenebis (2,3-dimethylcyclopentadienyl) titanium dichloride, isopropylidenebis (2,4 -Dimethylcyclopentadienyl) titanium dichloride, isopropylidenebis (2,5-dimethylcyclopentadienyl) titanium dichloride, isopropylidenebis (3,4-dimethylcyclopentadienyl) Titanium dichloride, isopropylidenebis (2,3-ethylmethylcyclopentadienyl) titanium dichloride, isopropylidenebis (2,4-ethylmethylcyclopentadienyl) titanium dichloride, isopropylidenebis (2,5-ethylmethylcyclo) Pentadienyl) titanium dichloride, isopropylidenebis (3,5-ethylmethylcyclopentadienyl) titanium dichloride, isopropylidenebis (2,3,4-trimethylcyclopentadienyl) titanium dichloride, isopropylidenebis (2, 3,5-trimethylcyclopentadienyl) titanium dichloride, isopropylidenebis (tetramethylcyclopentadienyl) titanium dichloride, isopropylidenebis (indenyl) titanium dichloride, isopropyl Pyridenebis (4,5,6,7-tetrahydroindenyl) titanium dichloride, isopropylidenebis (2-phenylindenyl) titanium dichloride, isopropylidenebis (2-methylindenyl) titanium dichloride, isopropylidenebis (2-methyl) -4-phenylindenyl) titanium dichloride, isopropylidenebis (2-methyl-4-naphthylindenyl) titanium dichloride, isopropylidenebis (2-methyl-4,5-benzoindenyl) titanium dichloride, isopropylidenebis ( Fluorenyl) titanium dichloride, isopropylidene (cyclopentadienyl) (tetramethylcyclopentadienyl) titanium dichloride, isopropylidene (cyclopentadienyl) (indenyl) titanium dichloride, Isopropylidene (methylcyclopentadienyl) (indenyl) titanium dichloride, isopropylidene (n-butylcyclopentadienyl) (indenyl) dichloride, isopropylidene (tetramethylcyclopentadienyl) (indenyl) dichloride, isopropylidene (cyclo Pentadienyl) (fluorenyl) titanium dichloride, isopropylidene (methylcyclopentadienyl) (fluorenyl) titanium dichloride, isopropylidene (n-butylcyclopentadienyl) (fluorenyl) titanium dichloride, isopropylidene (tetramethylcyclopentadiene) Enyl) (fluorenyl) titanium dichloride, isopropylidene (indenyl) (fluorenyl) titanium dichloride,

Dimethylsilylenebis (cyclopentadienyl) titanium dichloride, dimethylsilylenebis (2-methylcyclopentadienyl) titanium dichloride, dimethylsilylenebis (3-methylcyclopentadienyl) titanium dichloride, dimethylsilylenebis (2-n- Butylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (3-n-butylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (2,3-dimethylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (2,4 -Dimethylcyclopentadienyl) titanium dichloride, dimethylsilylenebis (2,5-dimethylcyclopentadienyl) titanium dichloride, dimethylsilylenebis (3,4-dimethylcyclopentadienyl) Titanium dichloride, dimethylsilylene bis (2,3-ethylmethylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (2,4-ethylmethylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (2,5-ethylmethylcyclo) Pentadienyl) titanium dichloride, dimethylsilylene bis (3,5-ethylmethylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (2,3,4-trimethylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (2, 3,5-trimethylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (tetramethylcyclopentadienyl) titanium dichloride, dimethylsilylene bis (indenyl) titanium dichloride, dimethyl Silylenebis (4,5,6,7-tetrahydroindenyl) titanium dichloride, dimethylsilylenebis (2-phenylindenyl) titanium dichloride, dimethylsilylenebis (2-methylindenyl) titanium dichloride, dimethylsilylenebis (2-methyl) -4-phenylindenyl) titanium dichloride, dimethylsilylenebis (2-methyl-4-naphthylindenyl) titanium dichloride, dimethylsilylenebis (2-methyl-4,5-benzoindenyl) titanium dichloride, dimethylsilylene (cyclo Pentadienyl) (indenyl) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (indenyl) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (indenyl) titanium di Chloride, dimethylsilylene (tetramethylcyclopentadienyl) (indenyl) titanium dichloride, dimethylsilylene (cyclopentadienyl) (fluorenyl) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (fluorenyl) titanium dichloride, dimethylsilylene ( n-butylcyclopentadienyl) (fluorenyl) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (indenyl) titanium dichloride, dimethylsilylene (indenyl) (fluorenyl) titanium dichloride,

Cyclopentadienyl titanium trichloride, pentamethylcyclopentadienyl titanium trichloride, cyclopentadienyl (dimethylamido) titanium dichloride, cyclopentadienyl (phenoxy) titanium dichloride, cyclopentadienyl (2,6-dimethylphenyl) ) Titanium dichloride, cyclopentadienyl (2,6-diisopropylphenyl) titanium dichloride, cyclopentadienyl (2,6-di-tert-butylphenyl) titanium dichloride, pentamethylcyclopentadienyl (2,6-dimethyl) Phenyl) titanium dichloride, pentamethylcyclopentadienyl (2,6-diisopropylphenyl) titanium dichloride, pentamethylcyclopentadienyl (2,6-di-tert-butylphenyl) Titanium dichloride, indenyl (2,6-diisopropylphenyl) titanium dichloride, fluorenyl (2,6-diisopropylphenyl) titanium dichloride,

Methylene (cyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, methylene (cyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, methylene (cyclopentadienyl) ( 3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, methylene (cyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, methylene (cyclopentadienyl) (3-tert-butyldimethyl) Silyl-5-methyl-2-phenoxy) titanium dichloride, methylene (cyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene (cyclopentadienyl) (3-tert-butyl- 5-methoxy-2-fu Noxy) titanium dichloride, methylene (cyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, methylene (methylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium Dichloride, methylene (methylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, methylene (methylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, Methylene (methylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, methylene (methylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene ( Methyl Clopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene (methylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, methylene (methyl Cyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, methylene (tert-butylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, methylene (tert -Butylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, methylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, methylene (Tert- Butylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, methylene (tert-butylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene ( tert-Butylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium Dichloride, methylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, methylene (tetramethylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) Titanium , Methylene (tetramethylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, methylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium Dichloride, methylene (tetramethylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, methylene (tetramethylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium Dichloride, methylene (tetramethylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) ) Titanium dichloride, methylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, methylene (trimethylsilylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) Titanium dichloride, methylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, methylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride , Methylene (trimethylsilylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, methylene (trimethylsilylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl -2-phenoxy) titanium dichloride, methylene (trimethylsilylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-methoxy) -2-phenoxy) titanium dichloride, methylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, methylene (fluorenyl) (3,5-dimethyl-2-phenoxy) titanium Dichloride, methylene (fluorenyl) (3-tert-butyl-2-phenoxy) titanium dichloride, methylene (fluorenyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, methyle (Fluorenyl) (3-phenyl-2-phenoxy) titanium dichloride, methylene (fluorenyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, methylene (fluorenyl) (3-trimethylsilyl-5- Methyl-2-phenoxy) titanium dichloride, methylene (fluorenyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, methylene (fluorenyl) (3-tert-butyl-5-chloro-2-phenoxy) Titanium dichloride,

Isopropylidene (cyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, isopropylidene (cyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, isopropylidene (cyclopentadi) Enyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (cyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, isopropylidene (cyclopentadienyl) (3 -Tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (cyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (cyclopente) Dienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, isopropylidene (cyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, isopropylidene (methyl) Cyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, isopropylidene (methylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, isopropylidene (methylcyclopentadienyl) ) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (methylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, isopropylidene (methylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (methylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (methylcyclohexane) Pentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, isopropylidene (methylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, isopropyl Riden (tert-butylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, isopropylidene (tert-butylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride Isopropylidene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (tert-butylcyclopentadienyl) (3-phenyl-2-phenoxy) ) Titanium dichloride, isopropylidene (tert-butylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (tert-butylcyclopentadienyl) (3-trimethylsilyl) -5-methyl-2-phenoxy) titanium dichloride, isopropylidene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, isopropylidene (tert Butylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, isopropylidene (tetramethylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, isopropylidene (Tetramethylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, isopropylidene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, Isopropylidene (tetramethylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, isopropylidene (tetramethylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) Titanium dichloride, isopropylidene (tetramethylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methoxy- 2-phenoxy) titanium dichloride, isopropylidene (tetramethylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclopentadienyl) (3,5-dimethyl) -2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclopene) Tadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclo) Pentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, isopropylidene (trimethylsilylcyclopentadienyl) (3-tert-butyl) Ru-5-chloro-2-phenoxy) titanium dichloride, isopropylidene (fluorenyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, isopropylidene (fluorenyl) (3-tert-butyl-2-phenoxy) titanium dichloride Isopropylidene (fluorenyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (fluorenyl) (3-phenyl-2-phenoxy) titanium dichloride, isopropylidene (fluorenyl) (3-tert -Butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (fluorenyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, isopropylidene (full Reniru) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, isopropylidene (fluorenyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride,

Diphenylmethylene (cyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, diphenylmethylene (cyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, diphenylmethylene (cyclopentadi) Enyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (cyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, diphenylmethylene (cyclopentadienyl) (3 -Tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (cyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethyle (Cyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, diphenylmethylene (cyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, Diphenylmethylene (methylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, diphenylmethylene (methylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, diphenylmethylene (methyl Cyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (methylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, diphenylmethylene ( Tilcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (methylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride Diphenylmethylene (methylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, diphenylmethylene (methylcyclopentadienyl) (3-tert-butyl-5-chloro-2- Phenoxy) titanium dichloride, diphenylmethylene (tert-butylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, diphenylmethylene (tert-butylcyclopentadienyl) (3-tert-butyl) Ru-2-phenoxy) titanium dichloride, diphenylmethylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (tert-butylcyclopentadienyl) ( 3-phenyl-2-phenoxy) titanium dichloride, diphenylmethylene (tert-butylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (tert-butylcyclopenta) Dienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) Tandichloride, diphenylmethylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopentadienyl) (3,5-dimethyl-2 -Phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl) -2-phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopentadienyl) (3-phenyl-2-phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopentadienyl) (3- ert-Butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopentadienyl) (3-trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopenta) Dienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, diphenylmethylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, diphenyl Methylene (trimethylsilylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, diphenylmethylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-2-phenoxy) Ii) Titanium dichloride, diphenylmethylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (trimethylsilylcyclopentadienyl) (3-phenyl-2-phenoxy) Titanium dichloride, diphenylmethylene (trimethylsilylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (trimethylsilylcyclopentadienyl) (3-trimethylsilyl-5-methyl- 2-phenoxy) titanium dichloride, diphenylmethylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride , Diphenylmethylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, diphenylmethylene (fluorenyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, diphenylmethylene ( Fluorenyl) (3-tert-butyl-2-phenoxy) titanium dichloride, diphenylmethylene (fluorenyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (fluorenyl) (3-phenyl-2) -Phenoxy) titanium dichloride, diphenylmethylene (fluorenyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (fluorenyl) ( -Trimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, diphenylmethylene (fluorenyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, diphenylmethylene (fluorenyl) (3-tert-butyl-5 -Chloro-2-phenoxy) titanium dichloride,

Dimethylsilylene (cyclopentadienyl) (2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3,5-dimethyl -2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3-tert-butyl-5-methyl-2) -Phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3,5-di-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (5-methyl-3-phenyl-2) -Phenoxy Titanium dichloride, dimethylsilylene (cyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (5-methyl-3-trimethylsilyl-2- Phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3-tert-butyl-5-chloro-) 2-phenoxy) titanium dichloride, dimethylsilylene (cyclopentadienyl) (3,5-diamil-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (2-phenoxy) titanium dichloride, Methylsilylene (methylcyclopentadienyl) (3-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopenta Dienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopenta) Dienyl) (3,5-di-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (5-methyl-3-phenyl-2-phenoxy) titanium dichloride, dimethylsilylene (methyl) Lucyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (5-methyl-3-trimethylsilyl-2-phenoxy) titanium dichloride Dimethylsilylene (methylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (3-tert-butyl-5-chloro-2-) Phenoxy) titanium dichloride, dimethylsilylene (methylcyclopentadienyl) (3,5-diamil-2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (2-phenoxy) titanium dichloride, dimethylsilane Len (n-butylcyclopentadienyl) (3-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, dimethylsilylene ( n-butylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride Dimethylsilylene (n-butylcyclopentadienyl) (3,5-di-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (5-methyl-3-phenyl- 2-phenoxy) titanium dichloride, dimethyl Silylene (n-butylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (5-methyl-3-trimethylsilyl- 2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (3- tert-butyl-5-chloro-2-phenoxy) titanium dichloride, dimethylsilylene (n-butylcyclopentadienyl) (3,5-diamil-2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) ) (2-F Enoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) Titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methyl- 2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3,5-di-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadiene) ) (5-methyl-3-phenyl-2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, dimethyl Silylene (tert-butylcyclopentadienyl) (5-methyl-3-trimethylsilyl-2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-) Phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, dimethylsilylene (tert-butylcyclopentadienyl) (3,5- The Mil-2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (3-methyl-2-phenoxy) titanium dichloride, dimethyl Silylene (tetramethylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (3-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene ( Tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (3,5-di-tert-butyl-2- Phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (5-methyl-3-phenyl-2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (3-tert-butyldimethylsilyl- 5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (5-methyl-3-trimethylsilyl-2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (3- tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, dimethylsilylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, dimethyl Silylene (tetramethylcyclopentadienyl) (3,5-diamil-2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) ( 3-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (3-tert-butyl- 2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, dimethyl Rylene (trimethylsilylcyclopentadienyl) (3,5-di-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (5-methyl-3-phenyl-2-phenoxy) titanium dichloride Dimethylsilylene (trimethylsilylcyclopentadienyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (5-methyl-3-trimethylsilyl-2- Phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (3-tert-butyl-5-methoxy-2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilyl) Lucyclopentadienyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, dimethylsilylene (trimethylsilylcyclopentadienyl) (3,5-diamil-2-phenoxy) titanium dichloride, dimethylsilylene ( Indenyl) (2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (3-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) ) (3-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) ( , 5-Di-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (5-methyl-3-phenyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (3-tert-butyldimethylsilyl) -5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (5-methyl-3-trimethylsilyl-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (3-tert-butyl-5-methoxy-2) -Phenoxy) titanium dichloride, dimethylsilylene (indenyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, dimethylsilylene (indenyl) (3,5-diamil-2-phenoxy) titanium dichlori Dimethylsilylene (fluorenyl) (2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3,5-dimethyl-2-phenoxy) titanium dichloride, Dimethylsilylene (fluorenyl) (3-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3 5-Di-tert-butyl-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (5-methyl-3-phenyl-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3-tert-butyldimethylsilyl-5-methyl-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (5-methyl-3-trimethylsilyl-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3-tert -Butyl-5-methoxy-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3-tert-butyl-5-chloro-2-phenoxy) titanium dichloride, dimethylsilylene (fluorenyl) (3,5-diamil-2) -Phenoxy) titanium dichloride and dimethylsilylene (tetramethylcyclopentadienyl)) (1-naphthoxy-2-yl) titanium dichloride, (2-phenoxy) of these compounds (3-phenyl-2-phenoxy) (3-trimethylsilyl-2-phenoxy) or a compound in which (3-tert-butyldimethylsilyl-2-phenoxy) is replaced, a compound in which dimethylsilylene in these compounds is replaced with diethylsilylene, diphenylsilylene, or dimethoxysilylene, In addition, the dichloride of these compounds was replaced with difluoride, dibromide, diiodide dimethyl, diethyl, diisopropyl, bis (dimethylamide), bis (diethylamide), dimethoxide, diethoxide, di-n-butoxide, diisopropoxide. A compound can be illustrated.

As a transition metal compound represented by formula (4), wherein M ¹ is a titanium atom, (tert-butylamido) tetramethylcyclopentadienyl-1,2-ethanediyltitanium dichloride, (tert-butylamido) tetra Methylcyclopentadienyl-1,2-ethanediyltitanium dimethyl, (tert-butylamido) tetramethylcyclopentadienyl-1,2-ethanediyltitanium dibenzyl, (methylamido) tetramethylcyclopentadienyl-1,2, -Ethanediyl titanium dichloride, (ethylamido) tetramethylcyclopentadienyl-1,2-ethanediyl titanium dichloride, (tert-butylamido) tetramethylcyclopentadienyldimethylsilane titanium dichloride, (tert-butylamido) te Methylcyclopentadienyldimethylsilanetitanium dimethyl, (tert-butyramide) tetramethylcyclopentadienyldimethylsilanetitanium dibenzyl, (benzylamido) tetramethylcyclopentadienyldimethylsilanetitanium dichloride, (phenylphosphide) tetramethylcyclo Pentadienyldimethylsilane titanium dibenzyl, (tert-butylamido) indenyl-1,2-ethanediyltitanium dichloride, (tert-butylamido) indenyl-1,2-ethanediyltitanium dimethyl, (tert-butylamido) tetrahydroindenyl- 1,2-ethanediyltitanium dichloride, (tert-butylamido) tetrahydroindenyl-1,2-ethanediyltitanium dimethyl, (tert-butyl Amido) fluorenyl-1,2-ethanediyl titanium dichloride, (tert-butylamido) fluorenyl-1,2-ethanediyl titanium dimethyl, (tert-butylamido) indenyldimethylsilane titanium dichloride, (tert-butylamido) indenyldimethylsilane Titanium dimethyl, (tert-butylamido) tetrahydroindenyldimethylsilane titanium dichloride, (tert-butylamido) tetrahydroindenyldimethylsilane titanium dimethyl, (tert-butylamido) fluorenyldimethylsilane titanium dichloride, (tert-butylamido) fluorenyl Dimethylsilane titanium dimethyl,

(Dimethylaminomethyl) tetramethylcyclopentadienyl titanium (III) dichloride, (dimethylaminoethyl) tetramethylcyclopentadienyl titanium (III) dichloride, (dimethylaminopropyl) tetramethylcyclopentadienyl titanium (III) dichloride (N-pyrrolidinylethyl) tetramethylcyclopentadienyl titanium dichloride, (B-dimethylaminoborabenzene) cyclopentadienylzirconium dichloride, cyclopentadienyl (9-mesitylboraanthracenyl) zirconium dichloride,

2,2′-thiobis (4-methyl-6-tert-butylphenoxy) titanium dichloride, 2,2′-thiobis [4-methyl-6- (1-methylethyl) phenoxy] titanium dichloride, 2,2′- Thiobis (4,6-dimethylphenoxy) titanium dichloride, 2,2'-methylenebis (4-methyl-6-tert-butylphenoxy) titanium dichloride, 2,2'-ethylenebis (4-methyl-6-tert-butyl) Phenoxy) titanium dichloride, 2,2'-sulfinylbis (4-methyl-6-tert-butylphenoxy) titanium dichloride, 2,2 '-(4,4', 6,6'-tetra-tert-butyl-1 , 1′biphenoxy) titanium dichloride, 2,2′-thiobis (4-methyl-6-tert-butylpheno) Ii) Titanium diisopropoxide, 2,2'-methylenebis (4-methyl-6-tert-butylphenoxy) titanium diisopropoxide, 2,2'-ethylenebis (4-methyl-6-tert-butylphenoxy) ) Titanium diisopropoxide, 2,2′-sulfinylbis (4-methyl-6-tert-butylphenoxy) titanium diisopropoxide,

(Di-tert-butyl-1,3-propanediamide) titanium dichloride, (dicyclohexyl-1,3-propanediamide) titanium dichloride, [bis (trimethylsilyl) -1,3-propanediamide] titanium dichloride, [bis ( tert-butyldimethylsilyl) -1,3-propanediamide] titanium dichloride, [bis (2,6-dimethylphenyl) -1,3-propanediamide] titanium dichloride, [bis (2,6-diisopropylphenyl) -1 , 3-propanediamide] titanium dichloride, [bis (2,6-di-tert-butylphenyl) -1,3-propanediamide] titanium dichloride, [bis (triisopropylsilyl) naphthalenediamide] titanium dichloride, [bis ( Trimethylsilyl) naphth Range amide] titanium dichloride, [bis (tert- butyldimethylsilyl) naphthalene diamide] titanium dichloride, [bis (tert- butyldimethylsilyl) naphthalene diamide] titanium dibromide,

[Hydrotris (3,5-dimethylpyrazolyl) borate] titanium trichloride, [hydrotris (3,5-dimethylpyrazolyl) borate] titanium tribromide, [hydrotris (3,5-dimethylpyrazolyl) borate] titanium triiodide, [ Hydrotris (3,5-diethylpyrazolyl) borate] titanium trichloride, [hydrotris (3,5-diethylpyrazolyl) borate] titanium tribromide, [hydrotris (3,5-diethylpyrazolyl) borate] titanium triiodide, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] titanium trichloride, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] titanium tribromide, [hydrotris (3,5-di-t rt-butylpyrazolyl) borate] titanium triiodide, [tris (3,5-dimethylpyrazolyl) methyl] titanium trichloride, [tris (3,5-dimethylpyrazolyl) methyl] titanium tribromide, [tris (3,5 -Dimethylpyrazolyl) methyl] titanium triiodide, [tris (3,5-diethylpyrazolyl) methyl] titanium trichloride, [tris (3,5-diethylpyrazolyl) methyl] titanium tribromide, [tris (3,5- Diethylpyrazolyl) methyl] titanium triiodide, [tris (3,5-di-tert-butylpyrazolyl) methyl] titanium trichloride, [tris (3,5-di-tert-butylpyrazolyl) methyl] titanium tribromide, [Tris (3,5-di-tert-butyl Rupirazoriru) methyl] titanium triiodide,

μ-oxobis [isopropylidene (cyclopentadienyl) (2-phenoxy) titanium chloride], μ-oxobis [isopropylidene (cyclopentadienyl) (2-phenoxy) titanium methoxide], μ-oxobis [isopropylidene ( Cyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium chloride], μ-oxobis [isopropylidene (cyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) ) Titanium methoxide], μ-oxobis [isopropylidene (methylcyclopentadienyl) (2-phenoxy) titanium chloride], μ-oxobis [isopropylidene (methylcyclopentadienyl) (2-phenoxy) titanium methoxide] , Μ-oxobis [isopropyl Den (methylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium chloride], μ-oxobis [isopropylidene (methylcyclopentadienyl) (3-tert-butyl-5-methyl) -2-phenoxy) titanium methoxide], μ-oxobis [isopropylidene (tetramethylcyclopentadienyl) (2-phenoxy) titanium chloride], μ-oxobis [isopropylidene (tetramethylcyclopentadienyl) (2- Phenoxy) titanium methoxide], μ-oxobis [isopropylidene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium chloride], μ-oxobis [isopropylidene (tetramethylcyclo) Pentadienyl) (3-t rt-butyl-5-methyl-2-phenoxy) titanium methoxide], μ-oxobis [dimethylsilylene (cyclopentadienyl) (2-phenoxy) titanium chloride], μ-oxobis [dimethylsilylene (cyclopentadienyl) (2-phenoxy) titanium methoxide], μ-oxobis [dimethylsilylene (cyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium chloride], μ-oxobis [dimethylsilylene (cyclopenta) Dienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium methoxide], μ-oxobis [dimethylsilylene (methylcyclopentadienyl) (2-phenoxy) titanium chloride], μ-oxobis [dimethyl Silylene (methylcyclopentadienyl) ( 2-phenoxy) titanium methoxide], μ-oxobis [dimethylsilylene (methylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium chloride], μ-oxobis [dimethylsilylene (methylcyclohexane) Pentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium methoxide], μ-oxobis [dimethylsilylene (tetramethylcyclopentadienyl) (2-phenoxy) titanium chloride], μ-oxobis [Dimethylsilylene (tetramethylcyclopentadienyl) (2-phenoxy) titanium methoxide], μ-oxobis [dimethylsilylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) Titanium chloride], μ-oxobis Dimethylsilylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium methoxide], di-μ-oxobis [isopropylidene (cyclopentadienyl) (2-phenoxy) titanium ], Di- [mu] -oxobis [isopropylidene (cyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium], di- [mu] -oxobis [isopropylidene (methylcyclopentadienyl) ( 2-phenoxy) titanium], di-μ-oxobis [isopropylidene (methylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium], di-μ-oxobis [isopropylidene (tetra Methylcyclopentadienyl) (2-phenoxy) titanium], di-μ-oxy Bis [isopropylidene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium], di-μ-oxobis [dimethylsilylene (cyclopentadienyl) (2-phenoxy) titanium ], Di- [mu] -oxobis [dimethylsilylene (cyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium], di- [mu] -oxobis [dimethylsilylene (methylcyclopentadienyl) ( 2-phenoxy) titanium], di-μ-oxobis [dimethylsilylene (methylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium], di-μ-oxobis [dimethylsilylene (tetra Methylcyclopentadienyl) (2-phenoxy) titanium] and di-μ-o Xoxobis [dimethylsilylene (tetramethylcyclopentadienyl) (3-tert-butyl-5-methyl-2-phenoxy) titanium] can be exemplified.

Examples of the transition metal compound represented by formula (4) in which M ¹ is a zirconium atom or a hafnium atom include compounds in which the titanium atom in the titanium compound is replaced with a zirconium atom or a hafnium atom.

Examples of the transition metal compound represented by formula (4) in which M ¹ is a vanadium atom include vanadium acetylacetonate, vanadium tetrachloride, and vanadium oxytrichloride.

An example of the transition metal compound represented by formula (4) where M ¹ is a samarium atom is bis (pentamethylcyclopentadienyl) samarium methyltetrahydrofuran.

Examples of the transition metal compound represented by the formula (4) in which M ¹ is an ytterbium atom include bis (pentamethylcyclopentadienyl) ytterbium methyltetrahydrofuran.

As a transition metal compound represented by formula (4), wherein M ¹ is a palladium atom, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-dimethyloxazoline] palladium dichloride, 2,2 '-Methylenebis [(4R) -4-phenyl-5,5'-dimethyloxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-phenyl-5,5'-diethyloxazoline] palladium dichloride, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-diethyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-di-n -Propyloxazoline] palladium dichloride, 2,2'-methylenebis [(4R) -4-phenyl-5,5'-di-n-propyloxazoline Palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-diisopropyloxazoline] palladium dichloride, 2,2′-methylenebis [(4R) -4-phenyl-5,5′- Diisopropyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-dicyclohexyloxazoline] palladium dichloride, 2,2′-methylenebis [(4R) -4-phenyl-5, 5'-dicyclohexyloxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-phenyl-5,5'-dimethoxyoxazoline] palladium dichloride, 2,2'-methylenebis [(4R) -4-phenyl -5,5'-dimethoxyoxazoline] palladium dibromide, 2 , 2′-methylenebis [(4R) -4-phenyl-5,5′-diethoxyoxazoline] palladium dichloride, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-diethoxyoxazoline] Palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-diphenyloxazoline] palladium dichloride, 2,2′-methylenebis [(4R) -4-phenyl-5,5′- Diphenyloxazoline] palladium dibromide,

Methylenebis [(4R) -4-methyl-5,5′-di- (2-methylphenyl) oxazoline] palladium dibromide, methylenebis [(4R) -4-methyl-5,5′-di- (3-methyl) Phenyl) oxazoline] palladium dibromide, methylenebis [(4R) -4-methyl-5,5′-di- (4-methylphenyl) oxazoline] palladium dibromide, methylenebis [(4R) -4-methyl-5,5 '-Di- (2-methoxyphenyl) oxazoline] palladium dibromide, methylenebis [(4R) -4-methyl-5,5'-di- (3-methoxyphenyl) oxazoline] palladium dibromide, methylenebis [(4R) -4-methyl-5,5'-di- (4-methoxyphenyl) oxazoline] palladium dibromide, Tylene bis [spiro {(4R) -4-methyloxazoline-5,1'-cyclobutane}] palladium dibromide, methylenebis [spiro {(4R) -4-methyloxazoline-5,1'-cyclopentane}] palladium dibromide , Methylenebis [spiro {(4R) -4-methyloxazoline-5,1'-cyclohexane}] palladium dibromide, methylenebis [spiro {(4R) -4-methyloxazoline-5,1'-cycloheptane}] palladium dibromide bromide,

2,2′-methylenebis [(4R) -4-isopropyl-5,5′-dimethyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isopropyl-5,5′-diethyloxazoline] Palladium dibromide, 2,2′-methylenebis [(4R) -4-isopropyl-5,5′-di-n-propyloxazoline] palladium dibromide, methylenebis [(4R) -4-isopropyl-5,5′- Diisopropyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isopropyl-5,5′-dicyclohexyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isopropyl-5 , 5′-diphenyloxazoline] palladium dibromide, 2, '-Methylenebis [(4R) -4-isopropyl-5,5'-di- (2-methylphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-isopropyl-5,5' -Di- (3-methylphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-isopropyl-5,5'-di- (4-methylphenyl) oxazoline] palladium dibromide, 2 , 2′-methylenebis [(4R) -4-isopropyl-5,5′-di- (2-methoxyphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isopropyl-5, 5′-di- (3-methoxyphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4 Isopropyl-5,5′-di- (4-methoxyphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-isopropyloxazoline-5,1′-cyclobutane}] palladium dibromide 2,2'-methylenebis [spiro {(4R) -4-isopropyloxazoline-5,1'-cyclopentane}] palladium dibromide, 2,2'-methylenebis [spiro {(4R) -4-isopropyloxazoline- 5,1′-cyclohexane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-isopropyloxazoline-5,1′-cycloheptane}] palladium dibromide, 2,2′-methylenebis [ (4R) -4-isobutyl-5,5′-dimethyloxazoline] Palladium dibromide, 2,2′-methylenebis [(4R) -4-isobutyl-5,5′-diethyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isobutyl-5,5 ′ -Di-n-propyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isobutyl-5,5′-diisopropyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R ) -4-Isobutyl-5,5'-dicyclohexyloxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-isobutyl-5,5'-diphenyloxazoline] palladium dibromide, 2,2'- Methylenebis [(4R) -4-isobutyl-5,5′-di- (2-methylphenyl) Xazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isobutyl-5,5′-di- (3-methylphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isobutyl-5,5'-di- (4-methylphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-isobutyl-5,5'-di- (2-methoxy) Phenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-isobutyl-5,5′-di- (3-methoxyphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [( 4R) -4-isobutyl-5,5′-di- (4-methoxyphenyl) oxazoline] palladium dibromide, 2 2′-methylenebis [spiro {(4R) -4-isobutyloxazoline-5,1′-cyclobutane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-isobutyloxazoline-5,1 ′ -Cyclopentane}] palladium dibromide, 2,2'-methylenebis [spiro {(4R) -4-isobutyloxazoline-5,1'-cyclohexane}] palladium dibromide, 2,2'-methylenebis [spiro {(4R ) -4-isobutyloxazoline-5,1′-cycloheptane}] palladium dibromide, 2,2′-methylenebis [(4R) -4-tert-butyl-5,5′-dimethyloxazoline] palladium dibromide, 2 , 2′-methylenebis [(4R) -4-tert-butyl-5,5′-die [Luxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4--4-tert-butyl-5,5′-di-n-propyloxazoline] palladium dibromide, 2,2′-methylenebis [( 4R) -4-tert-butyl-5,5′-di-isopropyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-tert-butyl-5,5′-diphenyloxazoline] palladium di Bromide, 2,2′-methylenebis [(4R) -4-tert-butyl-5,5′-dicyclohexyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-tert-butyl-5, 5'-di- (2-methylphenyl) oxazoline] palladium dibromide, 2,2'-methyle Bis [(4R) -4-tert-butyl-5,5′-di- (3-methylphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-tert-butyl-5, 5′-di- (4-methylphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-tert-butyl-5,5′-di- (2-methoxyphenyl) oxazoline] palladium Dibromide, 2,2'-methylenebis [(4R) -4-tert-butyl-5,5'-di- (3-methoxyphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R)- 4-tert-butyl-5,5′-di- (4-methoxyphenyl) oxazoline] palladium dibromide,

2,2′-methylenebis [spiro {(4R) -4-tert-butyloxazoline-5,1′-cyclobutane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-tert-butyl Oxazoline-5,1′-cyclopentane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-tert-butyloxazoline-5,1′-cyclohexane}] palladium dibromide, 2,2 '-Methylenebis [spiro {(4R) -4-tert-butyloxazoline-5,1'-cycloheptane}] palladium dibromide,

2,2′-methylenebis [(4R) -4-phenyl-5,5′-dimethyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-diethyloxazoline] Palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-di-n-propyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl- 5,5′-di-isopropyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-dicyclohexyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R ) -4-Phenyl-5,5′-diphenyloxazoline] palladium dibromide, 2,2′-methyle Bis [(4R) -4-phenyl-5,5′-di- (2-methylphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-di -(3-Methylpheni) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-phenyl-5,5'-di- (4-methylphenyl) oxazoline] palladium dibromide, 2,2 ' -Methylenebis [(4R) -4-phenyl-5,5'-di- (2-methoxyphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-phenyl-5,5'- Di- (3-methoxyphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-phenyl-5,5′-di- (4-me Kishifeniru) oxazoline] palladium dibromide,

2,2′-methylenebis [spiro {(4R) -4-phenyloxazoline-5,1′-cyclobutane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-phenyloxazoline-5, 1′-cyclopentane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-phenyloxazoline-5,1′-cyclohexane}] palladium dibromide, 2,2′-methylenebis [spiro { (4R) -4-phenyloxazoline-5,1′-cycloheptane}] palladium dibromide,

2,2′-methylenebis [(4R) -4-benzyl-5,5′-dimethyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-benzyl-5,5′-diethyloxazoline] Palladium dibromide, 2,2′-methylenebis [(4R) -4-benzyl-5,5′-di-n-propyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-benzyl- 5,5′-di-isopropyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-benzyl-5,5′-dicyclohexyloxazoline] palladium dibromide, 2,2′-methylenebis [(4R ) -4-Benzyl-5,5′-diphenyloxazoline] palladium dibromide, 2,2′-methyle Bis [(4R) -4-benzyl-5,5′-di- (2-methylphenyl) oxazoline] palladium dibromide, 2,2′-methylenebis [(4R) -4-benzyl-5,5′-di -(3-methylphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-benzyl-5,5'-di- (4-methylphenyl) oxazoline] palladium dibromide, 2,2 '-Methylenebis [(4R) -4-benzyl-5,5'-di- (2-methoxyphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-benzyl-5,5' -Di- (3-methoxyphenyl) oxazoline] palladium dibromide, 2,2'-methylenebis [(4R) -4-benzyl-5,5'-di- (4- Tokishifeniru) oxazoline] palladium dibromide,

2,2′-methylenebis [spiro {(4R) -4-benzyloxazoline-5,1′-cyclobutane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-benzyloxazoline-5, 1′-cyclopentane}] palladium dibromide, 2,2′-methylenebis [spiro {(4R) -4-benzyloxazoline-5,1′-cyclohexane}] palladium dibromide, and 2,2′-methylenebis [ Spiro {(4R) -4-benzyloxazoline-5,1′-cycloheptane}] palladium dibromide and compounds in which (4R) in each of the above compounds corresponds to (4S) can be exemplified. Further, as meso-type isomers, (4R) in each compound described above as an optically active bisoxazoline is exemplified by a compound in which one oxazoline skeleton is (4R) and the other oxazoline skeleton is (4S). be able to.

As the transition metal compound represented by the formula (4), wherein M ¹ is a palladium atom, [hydrotris (3,5-dimethylpyrazolyl) borate] palladium chloride, [hydrotris (3,5-dimethylpyrazolyl) borate] Palladium bromide, [hydrotris (3,5-dimethylpyrazolyl) borate] palladium iodide, [hydrotris (3,5-dimethylpyrazolyl) borate] palladium methyl, [hydrotris (3,5-dimethylpyrazolyl) borate] palladium ethyl, Hydrotris (3,5-dimethylpyrazolyl) borate] palladium allyl, [hydrotris (3,5-dimethylpyrazolyl) borate] palladium methallyl, [hydrotris (3,5-diethylpyrazolyl) borate] palladium chloride , [Hydrotris (3,5-diethylpyrazolyl) borate] palladium bromide, [hydrotris (3,5-diethylpyrazolyl) borate] palladium iodide, [hydrotris (3,5-diethylpyrazolyl) borate] palladium methyl, [hydrotris ( 3,5-diethylpyrazolyl) borate] palladium ethyl, [hydrotris (3,5-diethylpyrazolyl) borate] palladium allyl, [hydrotris (3,5-diethylpyrazolyl) borate] palladium methallyl, [hydrotris (3,5- Di-tert-butylpyrazolyl) borate] palladium chloride, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] palladium bromide, [hydrotris (3,5-di-tert-butyl) Pyrazolyl) borate] palladium iodide, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] palladium methyl, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] palladium ethyl, [hydrotris (3 , 5-di-tert-butylpyrazolyl) borate] palladium allyl, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] palladium methallyl,

Chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (aniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2 -Methylaniline-κN)] palladium, chloro (methyl) [N, N '-(ethane-1,2-diylidene) bis (2-ethylaniline-κN)] palladium, chloro (methyl) [N, N'- (Ethane-1,2-diylidene) bis (2-normalpropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-isopropylaniline-κN) ] Palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(D -1,2-diylidene) bis (2-isobutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-normalhexylaniline-κN)] Palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (4-methylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2- Diylidene) bis (2,6-dimethylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2,6-diethylaniline-κN)] palladium, chloro (Methyl) [N, N ′-(ethane-1,2-diylidene) bis (2,6-dinormalpropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane 1,2-diylidene) bis (2,6-diisopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2,6-dinormalbutylaniline) κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2,6-diisobutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane -1,2-diylidene) bis (2,6-dihexylhexylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-methyl-6- Ethylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-methyl-6-normalpropylaniline-κN)] palladium , Chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-methyl-6-isopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1 , 2-Diylidene) bis (2-methyl-6-butylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-ethyl-6-normalpropyl) Aniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-ethyl-6-isopropylaniline-κN)] palladium, chloro (methyl) [N, N '-(Ethane-1,2-diylidene) bis (2-ethyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N'-(ethane-1,2-diylidene) Bis (2-normalpropyl-6-isopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-normalpropyl-6-normalbutylaniline-κN) )] Palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis (2-isopropyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N′— (Ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2-methylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) ) Bis {2,4-dimethyl-6- (2-ethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) ) Bis {2,4-dimethyl-6- (2-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis {2,4- Dimethyl-6- (2-isopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2,6 -Dimethylphenyl) aniline- [kappa] N}] palladium, chloro (methyl) [N, N '-(ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2,6-diethylphenyl) aniline- [kappa] N}] palladium, chloro (methyl) [N, N '-(ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2,6-dinorpropylpropyl) aniline-κN}] para Palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2,6-diisopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2-methyl-6-ethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N '-(Ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2-methyl-6-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N'-( Ethane-1,2-diylidene) bis {2,4-dimethyl-6- (2-methyl-6-isopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1, 2 Diylidene) bis {2,4-dimethyl-6- (2-ethyl-6-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis {2,4-Dimethyl-6- (2-ethyl-6-isopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(ethane-1,2-diylidene) bis {2,4 -Dimethyl-6- (1-naphthyl) aniline-κN}] palladium,

Chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (aniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2 -Methylaniline-κN)] palladium, chloro (methyl) [N, N '-(butane-2,3-diylidene) bis (2-ethylaniline-κN)] palladium, chloro (methyl) [N, N'- (Butane-2,3-diylidene) bis (2-normalpropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-isopropylaniline-κN) ] Palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(bu -2,3-diylidene) bis (2-isobutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-normalhexylaniline-κN)] Palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (4-methylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3- Diylidene) bis (2,6-dimethylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2,6-diethylaniline-κN)] palladium, chloro (Methyl) [N, N ′-(butane-2,3-diylidene) bis (2,6-dinormalpropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane 2,3-diylidene) bis (2,6-diisopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2,6-dinormalbutylaniline- [kappa] N)] palladium, chloro (methyl) [N, N '-(butane-2,3-diylidene) bis (2,6-diisobutylaniline-κN)] palladium, chloro (methyl) [N, N'-(butane -2,3-diylidene) bis (2,6-dinormalhexylaniline-κN)] palladium, chloro (methyl) [N, N '-(butane-2,3-diylidene) bis (2-methyl-6- Ethylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-methyl-6-normalpropylaniline-κN)] palladium , Chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-methyl-6-isopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2) , 3-Diylidene) bis (2-methyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-ethyl-6-normal) Propylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-ethyl-6-isopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-ethyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-dii) Ridene) bis (2-normalpropyl-6-isopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-normalpropyl-6-normalbutylaniline) -ΚN)] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2-isopropyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N '-(Butane-2,3-diylidene) bis (2,4,6-trimethylaniline-κN)] palladium, chloro (methyl) [N, N'-(butane-2,3-diylidene) bis {2, 4-dimethyl-6- (2-methylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4 -Dimethyl-6- (2-ethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6- (2- Normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6- (2-isopropylphenyl) aniline-κN} ] Palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6- (2,6-dimethylphenyl) aniline-κN}] palladium, chloro (methyl ) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6- (2,6-diethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6- (2,6-dinormalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-( Butane-2,3-diylidene) bis {2,4-dimethyl-6- (2,6-diisopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3- Diylidene) bis {2,4-dimethyl-6- (2-methyl-6-ethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis { 2,4-dimethyl-6- (2-methyl-6-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4 -Jimee Ru-6- (2-methyl-6-isopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6 (2-Ethyl-6-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6- (2- Ethyl-6-isopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis {2,4-dimethyl-6- (1-naphthyl) aniline— κN}] palladium,

Chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bisaniline-κN] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthyl) Len-1,2-diylidene) bis (2-methylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2- Ethylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-normalpropylaniline-κN)] palladium, chloro (methyl ) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-isopropylaniline-κN)] palladium, chloro (methyl) [N, N′— (1,2-dihydroacenaphthylene-1,2-diylidene) bis (4-methylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1, 2-diylidene) bis (2-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-isobutylaniline) κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-normalhexylaniline-κN)] palladium, chloro (methyl) [N , N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,6-dimethylaniline-κN)] palladium, chloro (methyl) [N, N ′-( 1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,6-diethylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1) , 2-Diylidene) bis (2,6-dinormalpropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2 , 6-diisopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,6-dinormalbutylaniline-κN) ] Palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,6-diisobutylaniline-κN)] palladium, Loro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,6-dihexylaniline-κN)] palladium, chloro (methyl) [N, N '-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-methyl-6-ethylaniline-κN)] palladium, chloro (methyl) [N, N'-(1,2-dihydro Acenaphthylene-1,2-diylidene) bis (2-methyl-6-normalpropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2) -Diylidene) bis (2-methyl-6-isopropylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2 Methyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-ethyl-6-normalpropylaniline) -ΚN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-ethyl-6-isopropylaniline-κN)] palladium, chloro ( Methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-ethyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′ -(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-normalpropyl-6-isopropylaniline-κN)] palladium, chloro (methyl) ) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-normalpropyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′ -(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-isopropyl-6-normalbutylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydro Acenaphthylene-1,2-diylidene) bis (2,4,6-trimethylaniline-κN)] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2- Diylidene) bis {2,4-dimethyl-6- (2-methylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2) Diylidene) bis {2,4-dimethyl-6- (2-ethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) ) Bis {2,4-dimethyl-6- (2-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N '-(1,2-dihydroacenaphthylene-1,2-diylidene) ) Bis {2,4-dimethyl-6- (2-isopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) Bis {2,4-dimethyl-6- (2,6-dimethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2 -Diylidene) bis {2,4-dimethyl-6- (2,6-diethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1, 2-Diylidene) bis {2,4-dimethyl-6- (2,6-dinormalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene) -1,2-diylidene) bis {2,4-dimethyl-6- (2,6-diisopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthy Len-1,2-diylidene) bis {2,4-dimethyl-6- (2-methyl-6-ethylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2- Jihi Roacenaphthylene-1,2-diylidene) bis {2,4-dimethyl-6- (2-methyl-6-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2 -Dihydroacenaphthylene-1,2-diylidene) bis {2,4-dimethyl-6- (2-methyl-6-isopropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-( 1,2-dihydroacenaphthylene-1,2-diylidene) bis {2,4-dimethyl-6- (2-ethyl-6-normalpropylphenyl) aniline-κN}] palladium, chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis {2,4-dimethyl-6- (2-ethyl-6-isopropylphenyl) aniline-κN ] Palladium and chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis {2,4-dimethyl-6- (1-naphthyl) aniline-κN} ] Palladium can be exemplified.

As the transition metal compound represented by the formula (4) in which M ¹ is a nickel atom, a cobalt atom, a rhodium atom, or a ruthenium atom, the palladium atom in the palladium compound is replaced with a nickel atom, a cobalt atom, a rhodium atom, or ruthenium. Examples include compounds substituted with atoms.

As a transition metal compound represented by formula (4), wherein M ¹ is an iron atom, 2,6-bis- [1- (2,6-dimethylphenylimino) ethyl] pyridine iron dichloride, 2,6-bis -[1- (2,6-diisopropylphenylimino) ethyl] pyridine iron dichloride, 2,6-bis- [1- (2-tert-butyl-phenylimino) ethyl] pyridine iron dichloride, [hydrotris (3,5 -Dimethylpyrazolyl) borate] iron chloride, [hydrotris (3,5-dimethylpyrazolyl) borate] iron bromide, [hydrotris (3,5-dimethylpyrazolyl) borate] iron iodide, [hydrotris (3,5-dimethylpyrazolyl) Borate] iron methyl, [hydrotris (3,5- Methylpyrazolyl) borate] iron ethyl, [hydrotris (3,5-dimethylpyrazolyl) borate] iron allyl, [hydrotris (3,5-dimethylpyrazolyl) borate] iron methallyl, [hydrotris (3,5-diethylpyrazolyl) borate Iron chloride, [hydrotris (3,5-diethylpyrazolyl) borate] iron bromide, [hydrotris (3,5-diethylpyrazolyl) borate] iron iodide, [hydrotris (3,5-diethylpyrazolyl) borate] iron methyl, [Hydrotris (3,5-diethylpyrazolyl) borate] iron ethyl, [hydrotris (3,5-diethylpyrazolyl) borate] iron allyl, [hydrotris (3,5-diethylpyrazolyl) borate [Rate] Iron Metharyl, [Hydrotris (3,5-di-tert-butylpyrazolyl) borate] Iron Chloride, [Hydrotris (3,5-di-tert-butylpyrazolyl) borate] Iron Bromide, [Hydrotris (3,5 -Di-tert-butylpyrazolyl) borate] iron iodide, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] iron methyl, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] iron Examples thereof include ethyl, [hydrotris (3,5-di-tert-butylpyrazolyl) borate] iron allyl, and [hydrotris (3,5-di-tert-butylpyrazolyl) borate] iron methallyl.
Examples of the transition metal compound represented by formula (4) in which M ¹ is a cobalt atom or a nickel atom include compounds in which the iron atom in the iron compound is replaced with a cobalt atom or a nickel atom.
Two or more of the above transition metal compounds may be combined.

（ただし、上式［Ｉ］において、Ｍは元素の周期表第１０族の遷移金属原子を表し、Ｒ³およびＲ⁴はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、またはアリールオキシ基を表し、Ｒ⁵およびＲ⁶はそれぞれ独立に、炭素原子数１〜３０の炭化水素基を表し、Ｒ⁷およびＲ⁸はそれぞれ独立に、水素原子または炭素原子数１〜２０の炭化水素基を表し、Ｒ⁷とＲ⁸とは互いに結合していてもよい。） The transition metal compound is preferably a compound represented by the following formula [I].

(In the above formula [I], M represents a transition metal atom of Group 10 of the periodic table of elements, and R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group. Represents a substituted silyl group, an alkoxy group, an aralkyloxy group, or an aryloxy group, R ⁵ and R ⁶ each independently represent a hydrocarbon group having 1 to 30 carbon atoms, and R ⁷ and R ⁸ each independently Represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ⁷ and R ⁸ may be bonded to each other.)

Examples of the hydrocarbon group for R ⁷ and R ⁸ include an alkyl group and an aryl group. These groups may be substituted with groups such as halogen atoms, hydrocarbon oxy groups, nitro groups, sulfonyl groups, and silyl groups. Examples of the alkyl group include linear alkyl groups such as methyl, ethyl, and n-butyl groups; branched alkyl groups such as isopropyl, isobutyl, tert-butyl, and neopentyl groups; and cyclohexyl And a cyclic alkyl group such as a cyclooctyl group. Among them, preferred is an alkyl group having 1 to 20 carbon atoms, more preferred is a linear alkyl group having 1 to 12 carbon atoms, and further preferred is a methyl group or an ethyl group. Examples of the aryl group include a phenyl group, a naphthyl group, a 4-tolyl group, and a mesityl group. Among them, an aryl group having 6 to 20 carbon atoms is preferable, an aryl group having 6 to 12 carbon atoms is more preferable, and a phenyl group or a mesityl group is further preferable.

When R ⁷ and R ⁸ in the formula [I] are bonded to each other, examples of the ring formed by the bond include an aliphatic ring and an aromatic ring. These rings may have a substituent. Examples of the divalent group formed by the bond between R ⁷ and R ⁸ in the aliphatic ring include 1,2-ethylene group, 1,2-cyclohexylene group, 1,2-norbornene group, 2,3- Examples include butene, 2,3-dimethyl-2,3-butene, and 2,4-pentene. Examples of the divalent group formed by the bond between R ⁷ and R ⁸ in the aromatic ring include a 1,2-phenylene group and an acenaphthyl group, and an acenaphthyl group is preferable.

Examples of the hydrocarbon group having 1 to 30 carbon atoms of R ⁵ and R ⁶ in the formula [I] include an alkyl group, an aralkyl group, and an aryl group. These groups may have a substituent such as a halogen atom, a hydrocarbon oxy group, a nitro group, a sulfonyl group, and a silyl group.

  Examples of the alkyl group include linear alkyl groups such as methyl, ethyl, and n-butyl groups; branched alkyl groups such as isopropyl, isobutyl, tert-butyl, and neopentyl groups; and cyclohexyl and cyclo A cyclic alkyl group such as octyl can be exemplified. Among them, preferred is an alkyl group having 1 to 20 carbon atoms, more preferred is a branched alkyl group having 1 to 12 carbon atoms, and further preferred is an isopropyl group or a tert-butyl group.

  Examples of the aralkyl group include a benzyl group and a phenethyl group. Among them, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 12 carbon atoms, and further preferably a benzyl group.

  As the aryl group, phenyl group, 2-methylphenyl group, 2-ethylphenyl group, 2-normalpropylphenyl group, 2-isopropylphenyl group, 2-normalbutylphenyl group, 2-isobutylphenyl group, 2-normalhexyl Phenyl group, 4-methylphenyl group, 2,6-dimethylphenyl group, 2,6-diethylphenyl group, 2,6-dinormalpropylphenyl group, 2,6-diisopropylphenyl group, 2,6-dinormalbutyl Phenyl group, 2,6-diisobutylphenyl group, 2,6-dihexylphenyl group, 2-methyl-6-ethylphenyl group, 2-methyl-6-normalpropylphenyl group, 2-methyl-6-isopropylphenyl Group, 2-methyl-6-butylphenyl group, 2-ethyl-6-normalpropyl Phenyl group, 2-ethyl-6-isopropylphenyl group, 2-ethyl-6-normalbutylphenyl group, 2-normalpropyl-6-isopropylphenyl group, 2-normalpropyl-6-normalbutylphenyl group, 2-isopropyl -6-normal butylphenyl group, 2,4,6-trimethylphenyl group, 2,4-dimethyl-6- (2-methylphenyl) phenyl group, 2,4-dimethyl-6- (2-ethylphenyl) phenyl Group, 2,4-dimethyl-6- (2-normalpropylphenyl) phenyl group, 2,4-dimethyl-6- (2-isopropylphenyl) phenyl group, 2,4-dimethyl-6- (2,6- Dimethylphenyl) phenyl group, 2,4-dimethyl-6- (2,6-diethylphenyl) phenyl group, 2,4-dimethyl-6- ( , 6-Dinormalpropylphenyl) phenyl group, 2,4-dimethyl-6- (2,6-diisopropylphenyl) phenyl group, 2,4-dimethyl-6- (2-methyl-6-ethylphenyl) phenyl group 2,4-dimethyl-6- (2-methyl-6-normalpropylphenyl) phenyl group, 2,4-dimethyl-6- (2-methyl-6-isopropylphenyl) phenyl group, 2,4-dimethyl- 6- (2-ethyl-6-normalpropylphenyl) phenyl group, 2,4-dimethyl-6- (2-ethyl-6-isopropylphenyl) phenyl group, and 2,4-dimethyl-6- (1-naphthyl) ) A phenyl group can be exemplified. Among them, an aryl group having 6 to 30 carbon atoms is preferable, and an aryl group having 7 to 30 carbon atoms is more preferable.

Examples of the halogen atom of R ³ and R ⁴ in formula [I] include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among these, a chlorine atom or a bromine atom is preferable.

  Examples of the alkyl group include linear alkyl groups such as methyl, ethyl and n-butyl groups; branched alkyl groups such as isopropyl, isobutyl, tert-butyl and neopentyl groups; and cyclohexyl and cyclo A cyclic alkyl group such as octyl can be exemplified. Among them, preferably an alkyl group having 1 to 20 carbon atoms, more preferably a linear unsubstituted alkyl group having 1 to 12 carbon atoms, and further preferably a methyl group.

  Examples of the aralkyl group include a benzyl group and a phenethyl group. Among them, preferably an aralkyl group having 7 to 12 carbon atoms, more preferably an unsubstituted aralkyl group having 7 to 12 carbon atoms, and further preferably a benzyl group.

  Examples of the aryl group include a phenyl group, a naphthyl group, a 4-tolyl group, a mesityl group, and a 4-phenylphenyl group. Among them, an aryl group having 6 to 20 carbon atoms is preferable, an aryl group having 6 to 12 carbon atoms is more preferable, and a phenyl group, a 4-tolyl group, or a mesityl group is more preferable.

  As the substituted silyl group, a monosubstituted silyl group having 1 to 20 carbon atoms such as a methylsilyl group, an ethylsilyl group and a phenylsilyl group; 2 to 2 carbon atoms such as a dimethylsilyl group, a diethylsilyl group and a diphenylsilyl group 20 disubstituted silyl groups; trimethylsilyl group; triethylsilyl group; tri-n-propylsilyl group; triisopropylsilyl group; tri-n-butylsilyl group; tri-sec-butylsilyl group; tri-tert-butylsilyl group; Examples include silyl group; tert-butyldimethylsilyl group; tri-n-pentylsilyl group; tri-n-hexylsilyl group; tricyclohexylsilyl group; and triphenylsilyl group. Among them, a trisubstituted silyl group having 3 to 20 carbon atoms is preferable, and a trimethylsilyl group, a tert-butyldimethylsilyl group, or a triphenylsilyl group is more preferable.

  As the alkoxy group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, n-pentyloxy group, neopentyloxy group, n-hexyloxy Examples thereof include a group, an n-octyloxy group, an n-dodecyloxy group, an n-pentadecyloxy group, and an n-eicosyloxy group. Among them, preferred is an alkoxy group having 1 to 20 carbon atoms, more preferred is a methoxy group, an ethoxy group, an isopropoxy group or a tert-butoxy group.

  Examples of the aralkyloxy group include benzyloxy group, (2-methylphenyl) methoxy group, (3-methylphenyl) methoxy group, (4-methylphenyl) methoxy group, (2,3-dimethylphenyl) methoxy group, (2 4-dimethylphenyl) methoxy group, (2,5-dimethylphenyl) methoxy group, (2,6-dimethylphenyl) methoxy group, (3,4-dimethylphenyl) methoxy group, (3,5-dimethylphenyl) Methoxy group, (2,3,4-trimethylphenyl) methoxy group, (2,3,5-trimethylphenyl) methoxy group, (2,3,6-trimethylphenyl) methoxy group, (2,4,5-trimethyl) Phenyl) methoxy group, (2,4,6-trimethylphenyl) methoxy group, (3,4,5-trimethylphenyl) methoxy group, 2,3,4,5-tetramethylphenyl) methoxy group, (2,3,4,6-tetramethylphenyl) methoxy group, (2,3,5,6-tetramethylphenyl) methoxy group, (pentamethyl Phenyl) methoxy group, (ethylphenyl) methoxy group, (n-propylphenyl) methoxy group, (isopropylphenyl) methoxy group, (n-butylphenyl) methoxy group, (sec-butylphenyl) methoxy group, (tert-butyl) Examples include phenyl) methoxy group, (n-hexylphenyl) methoxy group, (n-octylphenyl) methoxy group, (n-decylphenyl) methoxy group, naphthylmethoxy group, and anthracenylmethoxy group. Among them, an aralkyloxy group having 7 to 20 carbon atoms is preferable, and a benzyloxy group is more preferable.

  As the aryloxy group, phenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2,3-dimethylphenoxy group, 2,4-dimethylphenoxy group, 2,5-dimethylphenoxy group 2,6-dimethylphenoxy group, 3,4-dimethylphenoxy group, 3,5-dimethylphenoxy group, 2-tert-butyl-3-methylphenoxy group, 2-tert-butyl-4-methylphenoxy group, 2 -Tert-butyl-5-methylphenoxy group, 2-tert-butyl-6-methylphenoxy group, 2,3,4-trimethylphenoxy group, 2,3,5-trimethylphenoxy group, 2,3,6-trimethyl Phenoxy group, 2,4,5-trimethylphenoxy group, 2,4,6-trimethylphenoxy group, 2-te t-butyl-3,4-dimethylphenoxy group, 2-tert-butyl-3,5-dimethylphenoxy group, 2-tert-butyl-3,6-dimethylphenoxy group, 2,6-di-tert-butyl- 3-methylphenoxy group, 2-tert-butyl-4,5-dimethylphenoxy group, 2,6-di-tert-butyl-4-methylphenoxy group, 3,4,5-trimethylphenoxy group, 2,3, 4,5-tetramethylphenoxy group, 2-tert-butyl-3,4,5-trimethylphenoxy group, 2,3,4,6-tetramethylphenoxy group, 2-tert-butyl-3,4,6- Trimethylphenoxy group, 2,6-di-tert-butyl-3,4-dimethylphenoxy group, 2,3,5,6-tetramethylphenoxy group, 2-tert-butyl 3,5,6-trimethylphenoxy group, 2,6-di-tert-butyl-3,5-dimethylphenoxy group, pentamethylphenoxy group, ethylphenoxy group, n-propylphenoxy group, isopropylphenoxy group, n-butyl Examples thereof include a phenoxy group, a sec-butylphenoxy group, a tert-butylphenoxy group, an n-hexylphenoxy group, an n-octylphenoxy group, an n-decylphenoxy group, a naphthoxy group, and an anthracenoxy group. Among these, an aryloxy group having 6 to 20 carbon atoms is preferable.

R ³ and R ⁴ in the formula [I] are preferably a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom, a halogen atom, or a linear unsubstituted alkyl having 1 to 12 carbon atoms. Group, particularly preferably a chlorine atom or a methyl group.

  M in the formula [I] is preferably a nickel atom or a palladium atom, more preferably a palladium atom.

（ただし、上式［ＩＩ］において、Ｍは元素の周期表第１０族の遷移金属原子を表し、Ｒ³およびＲ⁴はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、またはアリールオキシ基を表し、Ｒ⁷およびＲ⁸はそれぞれ独立に、水素原子または炭素原子数１〜２０の炭化水素基を表し、Ｒ⁷とＲ⁸とは互いに結合していてもよい、Ｒ⁹およびＲ¹⁰はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、置換シリル基、アルコキシ基、アラルキルオキシ基、２置換アミノ基、または炭化水素チオ基を表し、Ｒ¹¹およびＲ¹²はそれぞれ独立に炭素原子数７〜２０のアリール基を表し、Ｒ¹³およびＲ¹⁴はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、２置換アミノ基、または炭化水素チオ基を表す。）

（ただし、上式［ＩＩＩ］において、Ｍは元素の周期表第１０族の遷移金属原子を表し、Ｒ³およびＲ⁴はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、またはアリールオキシ基を表し、Ｒ⁷およびＲ⁸はそれぞれ独立に、水素原子または炭素原子数１〜２０の炭化水素基を表し、Ｒ⁷とＲ⁸とは互いに結合していてもよい。Ｒ¹⁵、Ｒ¹⁶、Ｒ¹⁷およびＲ¹⁸はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、炭素原子数６のアリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、２置換アミノ基、または炭化水素チオ基を表し、Ｒ¹⁹およびＲ²⁰はそれぞれ独立に、水素原子、ハロゲン原子、アルキル基、アラルキル基、アリール基、置換シリル基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、２置換アミノ基、または炭化水素チオ基を表す。） The transition metal compound used in the present invention is preferably represented by the above formula [I] from the viewpoint of producing a diisotactic triad polymer in which diisotactic triad (preferably, threodiisotactic triad) exceeds 25%. Of the compound represented by the following formula [II] belonging to the above-mentioned compound, wherein the dicindiotactic triad (preferably threodicindiotactic triad) exceeds 25%: To the compound represented by the following formula [III] belonging to the compound represented by the above formula [I].

(In the above formula [II], M represents a transition metal atom of Group 10 of the periodic table of elements, and R ³ and R ⁴ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group. , A substituted silyl group, an alkoxy group, an aralkyloxy group, or an aryloxy group, R ⁷ and R ⁸ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ⁷ and R ⁸ May be bonded to each other. R ⁹ and R ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, substituted silyl group, alkoxy group, aralkyloxy group, disubstituted amino group, or carbonized represents hydrogen thio group, R ¹¹ and R ¹² each independently represents an aryl group having 7 to 20 carbon atoms, each R ¹³ and R ¹⁴ are independently a hydrogen atom, a halogen atom Alkyl group, an aralkyl group, an aryl group, a substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, di-substituted amino group or a hydrocarbon thio group.)

(In the above formula [III], M represents a transition metal atom of Group 10 of the periodic table of elements, and R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group. , A substituted silyl group, an alkoxy group, an aralkyloxy group, or an aryloxy group, R ⁷ and R ⁸ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ⁷ and R ⁸ R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group having 6 carbon atoms, a substituted silyl group, alkoxy group, aralkyloxy group, an aryloxy group, an 2-substituted amino group or a hydrocarbon thio group,, R ¹⁹ and R ²⁰ are each independently a hydrogen atom, a halogen atom, alkyl Represents group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, an aryloxy group, a disubstituted amino group or a hydrocarbon thio group.)

R ⁹ and R ¹⁰ in the formula [II] are preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, particularly preferably a methyl group, an ethyl group, a normal propyl group, an isopropyl group, or a normal butyl group. , An isobutyl group, or a tert-butyl group.

As R ¹¹ and R ¹² in the formula [II], 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5- Dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 3,6-dimethylphenyl group, naphthyl group, 2-methyl-1-naphthyl group, 3- Methyl-1-naphthyl group, 4-methyl-1-naphthyl group, 2,3-dimethyl-1-naphthyl group, 2,4-dimethyl-1-naphthyl group, 2,5-dimethyl-1-naphthyl group, 2 , 6-dimethyl-1-naphthyl group, 3,4-dimethyl-1-naphthyl group, 3,5-dimethyl-1-naphthyl group, 3,6-dimethyl-1-naphthyl group, anthracenyl group, 2-methyl- -Anthracenyl group, 3-methyl-10-anthracenyl group, 4-methyl-10-anthracenyl group, 2,3-dimethyl-10-anthracenyl group, 2,4-dimethyl-10-anthracenyl group, 2,5-dimethyl- 1-10-anthracenyl group, 2,6-dimethyl-10-anthracenyl group, 3,4-dimethyl-10-anthracenyl group, 3,5-dimethyl-10-anthracenyl group, 3,6-dimethyl-10-anthracenyl group And 2-methyl-10-anthracenyl group. Among them, a substituted phenyl group, a naphthyl group, or an anthracenyl group is preferable, and a 2-methyl-phenyl group or a naphthyl group is more preferable.

R ¹³ and R ¹⁴ in formula [II] are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, still more preferably a methyl group, an ethyl group, a normal propyl group, or isopropyl. Group, normal butyl group, or isobutyl group.

  In the general formula [II], M is a transition metal atom of Group 10 of the periodic table of elements. M is preferably a nickel atom or a palladium atom, and more preferably a palladium atom.

R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ in the formula [III] are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or the number of carbon atoms. A 6-20 aryl group, more preferably a hydrogen atom, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a tert-butyl group, or a phenyl group.

R ¹⁹ and R ²⁰ in the formula [III] are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 20 carbon atoms. And more preferably a hydrogen atom, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, an ert-butyl group, or a phenyl group.

The organoaluminum compound in the present invention may be a known compound. Examples of the organoaluminum compound include the following compounds and combinations of one or more thereof.
(1) an organoaluminum compound represented by the formula E ¹ _d AlZ _3-d ;
(2) a cyclic aluminoxane represented by the formula {—Al (E ² ) —O—} _e ; and (3) a formula E ³ {—Al (E ³ ) —O—} _f AlE ³ _2. Linear aluminoxane;
However, in the above formula, E ¹ , E ² and E ³ each represent a hydrocarbon group, and when a plurality of E ¹ , a plurality of E ² or a plurality of E ³ are present, they are the same or different from each other. Z represents a hydrogen atom or a halogen atom, and when there are a plurality of Z, they are the same or different. d represents a number satisfying 0 <d ≦ 3, e is an integer of 2 or more, preferably an integer of 2 to 40, and f is an integer of 1 or more, preferably an integer of 1 to 40 .

The hydrocarbon group for E ¹ , E ² and E ³ is preferably a hydrocarbon group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.

  As organoaluminum compounds represented by the above formula, trialkylaluminum such as trimethylaluminum, triethylaluminum, tripropylaluminum, triisobutylaluminum, and trihexylaluminum; dimethylaluminum chloride, diethylaluminum chloride, dipropylaluminum chloride, diisobutyl Dialkylaluminum chlorides such as aluminum chloride and dihexylaluminum chloride; alkylaluminum dichlorides such as methylaluminum dichloride, ethylaluminum dichloride, propylaluminum dichloride, isobutylaluminum dichloride, and hexylaluminum dichloride; and dimethylaluminium Hydride, diethylaluminum hydride, can be exemplified dipropyl aluminum hydride, diisobutylaluminum hydride, and the dialkyl aluminum hydride such as dihexyl aluminum hydride. Among them, preferred is trialkylaluminum, and more preferred is triethylaluminum or triisobutylaluminum.

Examples of E ² and E ³ in the above formula include alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, normal pentyl group, and neopentyl group. Of these, a methyl group or an isobutyl group is preferable.

  The cyclic and linear aluminoxane represented by the above formula can be produced by various methods. Their production methods are not particularly limited, and may be known production methods. As a production method, a method in which a trialkylaluminum such as trimethylaluminum is dissolved in a suitable organic solvent such as benzene and an aliphatic hydrocarbon is brought into contact with water, and a trialkylaluminum such as trimethylaluminum is produced. An example is a method of producing by contacting with a metal salt containing water of crystallization, such as copper sulfate hydrate.

The boron compound in the present invention may be a known compound. As a boron compound, the following each compound and those 1 or more types of combinations can be illustrated.
(1) A boron compound represented by the formula BQ ¹ Q ² Q ³ ;
(2) Boron compound represented by formula G ⁺ (BQ ¹ Q ² Q ³ Q ⁴ ) ⁻ ; and (3) Formula (JH) ⁺ (BQ ¹ Q ² Q ³ Q ⁴ ) ^−. Boron compounds;
In the above formula, B represents a boron atom in a trivalent valence state, and Q ^{1 to} Q ⁴ each independently represent a halogen atom, a hydrocarbon group, a halogenated hydrocarbon group, a substituted silyl group, an alkoxy group, or Represents a disubstituted amino group, G ⁺ represents an inorganic or organic cation, J represents a neutral Lewis base, and (JH) ⁺ represents a Bronsted acid.

Q ^{1 to} Q ⁴ in the first to third formulas are preferably a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogenated hydrocarbon group having 1 to 20 carbon atoms, or 1 carbon atom. A substituted amino group substituted with a substituted silyl group having 20 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a hydrocarbon group having 2 to 20 carbon atoms, more preferably a halogen atom or 1 to 20 carbon atoms. Or a halogenated hydrocarbon group containing 1 to 20 carbon atoms, more preferably a fluorinated carbon atom having 1 to 20 carbon atoms containing at least one fluorine atom. A hydrogen group, particularly preferably a fluorinated aryl group having 6 to 20 carbon atoms and containing at least one fluorine atom.

  Examples of the boron compound represented by the above formula 1 include tris (pentafluorophenyl) borane, tris (2,3,5,6-tetrafluorophenyl) borane, and tris (2,3,4,5-tetrafluorophenyl). Examples include borane, tris (3,4,5-trifluorophenyl) borane, tris (2,3,4-trifluorophenyl) borane, and phenylbis (pentafluorophenyl) borane. Of these, tris (pentafluorophenyl) borane is most preferable.

Examples of G ⁺ that is an inorganic cation in the boron compound represented by the above formula 2 include a ferrocenium cation, an alkyl-substituted ferrocenium cation, and a silver cation. An example of G ⁺ that is an organic cation is a triphenylmethyl cation. G ⁺ is preferably a carbenium cation, particularly preferably a triphenylmethyl cation.

As (BQ ¹ Q ² Q ³ Q ⁴ ) ⁻ in the above formula ² , tetrakis (pentafluorophenyl) borate, tetrakis (2,3,5,6-tetrafluorophenyl) borate, tetrakis (2,3,4, 5-tetrafluorophenyl) borate, tetrakis (3,4,5-trifluorophenyl) borate, tetrakis (2,3,4-trifluorophenyl) borate, phenyltris (pentafluorophenyl) borate, and tetrakis ( 3,5-bistrifluoromethylphenyl) borate can be exemplified.

  As the boron compound represented by the above formula 2, lithium tetrakis (3,5-bistrifluoromethylphenyl) borate, sodium tetrakis (3,5-bistrifluoromethylphenyl) borate, potassium tetrakis (3,5-bistrifluoromethyl) Phenyl) borate, silver tetrakis (pentafluorophenyl) borate, ferrocenium tetrakis (pentafluorophenyl) borate, 1,1′-dimethylferrocenium tetrakis (pentafluorophenyl) borate, tetrabutylphosphonium tetrakis (pentafluorophenyl) Borate, tetraphenylphosphonium tetrakis (pentafluorophenyl) borate, tetramethylammonium tetrakis (pentafluorophenyl) borate, trimethylsulfo Examples include umtetrakis (pentafluorophenyl) borate, diphenyliodoniumtetrakis (pentafluorophenyl) borate, triphenylcarbeniumtetrakis (pentafluorophenyl) borate, and triphenylcarbeniumtetrakis (3,5-bistrifluoromethylphenyl) borate can do. Of these, triphenylcarbenium tetrakis (pentafluorophenyl) borate is most preferable.

Examples of (JH) ⁺ in the above formula 3 include trialkyl-substituted ammonium, N, N-dialkylanilinium, dialkylammonium and triarylphosphonium. (BQ ¹ Q ² Q ³ Q ⁴ ) ^- as it can be exemplified by the same manner as described above.

  Examples of the boron compound represented by the above formula 3 include triethylammonium tetrakis (pentafluorophenyl) borate, tripropylammonium tetrakis (pentafluorophenyl) borate, tri (n-butyl) ammonium tetrakis (pentafluorophenyl) borate, tri ( n-butyl) ammonium tetrakis (3,5-bistrifluoromethylphenyl) borate, N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate, N, N-diethylanilinium tetrakis (pentafluorophenyl) borate, N, N-dimethyl-2,4,6-trimethylanilinium tetrakis (pentafluorophenyl) borate, N, N-dimethylanilinium tetrakis (3,5-bistrifluoromethylphenol B) borate, diisopropylammonium tetrakis (pentafluorophenyl) borate, dicyclohexylammonium tetrakis (pentafluorophenyl) borate, triphenylphosphonium tetrakis (pentafluorophenyl) borate, tri (methylphenyl) phosphonium tetrakis (pentafluorophenyl) borate, and An example is tri (dimethylphenyl) phosphonium tetrakis (pentafluorophenyl) borate. Among these, tri (n-butyl) ammonium tetrakis (pentafluorophenyl) borate or N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate is most preferable.

  The boron compound in the present invention is preferably a boron compound represented by the above formula 2 or 3, and particularly preferably triphenylcarbenium tetrakis (pentafluorophenyl) borate or tri (n-butyl) ammonium tetrakis. (Pentafluorophenyl) borate or N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate.

  The molecular weight of the polymer of the present invention is not particularly limited, and the weight average molecular weight (Mw) is preferably 1,000 to 10,000,000, more preferably 2,000 to 5,000,000. Most preferably, it is 4,000 to 3,000,000.

  The molecular weight distribution of the polymer of this invention is not specifically limited, Preferably it is 1.0-100, More preferably, it is 1.0-50, Most preferably, it is 1.0-20.

  The glass transition point (measure of heat resistance) of the polymer of the present invention is preferably 60 ° C. or higher, more preferably 70 ° C. or higher, and most preferably 80 ° C. or higher.

  In the present invention, the method for contacting the transition metal compound, the organoaluminum compound and / or boron compound, and the monomer is not particularly limited.

  When a polymerization catalyst is produced by bringing a transition metal compound into contact with an organoaluminum compound, a cyclic aluminoxane, a linear aluminoxane, or a combination thereof is preferable as the organoaluminum compound from the viewpoint of increasing the activity of the polymerization catalyst. . In the case where a transition metal compound, an organoaluminum compound, and a boron compound are brought into contact with each other to form a polymerization catalyst, the organoaluminum compound represented by the above formula 1 is preferable as the organoaluminum compound from the same viewpoint.

  The usage-amount of an organoaluminum compound is 0.1-10000 mol part normally per 1 mol part of transition metal compounds, Preferably it is 5-2000 mol part. If the amount used is less than 0.1 mol part, sufficient polymerization activity cannot be obtained, and if it exceeds 10000 mol parts, the molecular weight of the resulting polymer decreases (for example, by chain transfer to an organoaluminum compound). ), The activity of the polymerization catalyst may decrease. The usage-amount of a boron compound is 0.01-100 mol part normally per 1 mol part of transition metal compounds, Preferably it is 0.5-10 mol part. When the amount used is less than 0.01 mole part, the activity of the polymerization catalyst may be insufficient, and the use exceeding 100 mole part is not preferable from the viewpoint of cost.

  Each of the transition metal compound, organoaluminum compound and boron compound in the present invention may be used as a solution. Examples of the solvent for the solution include methylene chloride, chloroform, toluene, pentane, hexane, and heptane. Among these, methylene chloride, chloroform, or toluene is preferable.

  The density | concentration of a transition metal compound solution is 0.01-500 micromol / L normally, Preferably it is 0.05-100 micromol / L, More preferably, it is 0.05-50 micromol / L. The density | concentration of an organoaluminum compound solution is 0.01-10000 micromol / L normally in conversion of an aluminum atom, Preferably it is 0.1-5000 micromol / L, More preferably, it is 0.1-2000 micromol / L. The density | concentration of a boron compound solution is 0.01-500 micromol / L normally, Preferably it is 0.05-200 micromol / L, More preferably, it is 0.05-100 micromol / L. When the concentration of the transition metal compound solution is less than 0.01 μmol / L, the concentration of the organoaluminum compound solution is less than 0.01 μmol / L in terms of aluminum atoms, or the concentration of the boron compound solution is 0.00. When the concentration is less than 01 μmol / L, a large amount of solvent is required, which is not preferable in terms of cost. When the concentration of the transition metal compound solution exceeds 500 μmol / L, or when the concentration of the organoaluminum compound solution is 10,000 μmol / When exceeding L, or when the concentration of the boron compound solution exceeds 500 μmol / L, these compounds may not be sufficiently dissolved and may precipitate.

  The polymerization catalyst in the present invention may be combined with a carrier comprising an inorganic compound particulate material or an organic compound particulate material. Examples of inorganic compounds include silica gel and alumina. A styrene polymer can be illustrated as an organic compound.

  The polymerization method in the present invention is not particularly limited. Examples of the method include batch type or continuous type gas phase polymerization method, bulk polymerization method, and solution polymerization method or slurry polymerization method using an appropriate polymerization solvent. The polymerization solvent is a solvent that does not deactivate the polymerization catalyst, and examples of the solvent include hydrocarbon solvents such as benzene, toluene, pentane, hexane, heptane, and cyclohexane, and halogenated solvents such as dichloromethane and chloroform. be able to.

The polymerization temperature in this invention is not specifically limited, Generally it is -100-250 degreeC, Preferably it is -50-200 degreeC. When the temperature is less than −100 ° C., the polymerization catalyst may not exhibit sufficient activity, and when it exceeds 250 ° C., the molecular weight of the resulting polymer may be reduced, or as in the isomerization reaction. Occurrence of such side reactions may result in failure to obtain a polymer composed of the repeating unit represented by the formula (1).
A chain transfer agent such as hydrogen may be used to adjust the molecular weight of the resulting polymer.

  The polymerization time in the present invention is not particularly limited, and is generally 1 minute to 72 hours. If the time is less than 1 minute, the yield of the polymer may be insufficient, and if it exceeds 72 hours, it is disadvantageous in terms of the production cost of the polymer.

  The polymer of the present invention can be used as a weathering agent, lubricant, pigment, dye, antistatic agent, antioxidant, antifogging agent, rust inhibitor, surfactant, lubricant, and conductive agent depending on the purpose. You may combine with various additives. The polymers of the present invention may also be combined with known polymers such as low density polyethylene, high density polyethylene, linear low density polyethylene, ethylene-α-olefin copolymer elastomers, and polypropylene.

  The polymer of the present invention can be used as an extrusion molded product or an injection molded product. The extrusion molding method may be a known molding method. As extrusion molding methods, an inflation molding method in which a molten resin is extruded from a circular die and a film or sheet expanded into a cylindrical shape is wound up, or a molten resin is extruded from a linear die and a T die in which the film or sheet is wound up A molding method and a calendar molding method can be exemplified.

  EXAMPLES Hereinafter, although this invention is demonstrated based on an Example, this invention is not limited to these Examples.

Example 1
(1) Monomer synthesis To a 25 mL Schlenk tube containing 0.0065 g of PdCl ₂ (CH ₃ CN) _{2 and} 0.95 mL of methylene chloride, 0.33 mL of P (OPh) ₃ was added under a nitrogen atmosphere. . After stirring for 15 minutes at room temperature, 0.07 mL of triethylamine and 4.54 μL of water were added, and the mixture was further stirred for 20 minutes. Further, 5 mL of water was added and stirred for 5 minutes, and then the upper aqueous layer was removed using a cannula. The remaining organic layer was distilled off, and the residue was washed with acetone to obtain Pd [P (OPh) ₃ ] ₄ (co-authored by Kashiwagi, Kada and Ashiya, “The Journal of Organic Chemistry ( The Journal of Organic Chemistry), 69, 2004, p. 2595).
In a 50 mL eggplant-shaped flask, 7.69 g of molecular sieve 3A, 35 mL of toluene, 49.7 mg of Pd (OPh) ₃ and Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) 5. 04g and allyl alcohol 4.9mL were added, and it stirred at 80 degreeC by nitrogen atmosphere for 2 hours. Toluene was distilled off after filtration, and the residue was purified by column chromatography using silica gel as the stationary phase and a mixed solvent of 8 parts by weight of hexane and 1 part by weight of ethyl acetate as the mobile phase to obtain a transparent oil 6.22 g of isopropylidene diallyl malonate (monomer) was obtained.

(2) Polymerization of monomer Chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,6-diisopropylaniline-κN)] palladium (transition metal) Compound) 6.57 mg and sodium tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound) 10.6 mg were added to a 25 mL Schlenk tube, and 0.5 mL of methylene chloride was added and stirred for 30 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 48 hours.
The number average molecular weight (Mn) of the obtained polymer is 8200, and the molecular weight distribution (Mw / Mn) represented by the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn) is 1.6. The steric positional relationship between the main chain of the polymer and the five-membered ring is 100% in the trans form, and the stereoregularity is 67% in the threodicindiotactic triad, and the glass is in the range of −60 ° C. to 150 ° C. No transition point was detected. The obtained results are shown in Table 1.

The above number average molecular weight and molecular weight distribution were measured by gel permeation chromatography (GPC) under the following conditions. A calibration curve was prepared using standard polystyrene.
Measuring instrument: manufactured by JASCO (Degasser: DG-980-50, pump: PU-980, autosampler: AS-950, column oven: CO-966, RI detector: RI-930, UV detector: UV-975 )
Column: Shodex-806L x 2 manufactured by Showa Denko KK Measurement temperature: 40 ° C
Solvent: Chloroform sample concentration: 1 mg / 1 ml

The glass transition point was measured under the following conditions by differential scanning calorimetry (DSC) measurement using a model named SSC-5200 manufactured by Seiko Instruments Inc.
Temperature rise: 25 ° C to 135 ° C (10 ° C / min) Hold for 5 minutes Cooling: 135 ° C to -60 ° C (20 ° C / min) Hold for 5 minutes Measurement: -60 ° C to 150 ° C (temperature rise at 10 ° C / min) )

The ratio of the above-mentioned transformer type was obtained under the following conditions by ¹³ C-NMR analysis using a model named LA-500 manufactured by JEOL.
Measuring solvent: chloroform-d ₁
Measurement temperature: room temperature
Sample concentration: 50 mg / 0.5 ml
Reference material: chloroform-d ₁ (77 ppm)

Said stereoregularity was calculated | required by the method which consists of the following procedures by the ¹³ C-NMR analysis using the model named LA-500 by JEOL.
(1) A deuterated chloroform solution (concentration: 286 mg / mL) of the polymer was prepared.
(2) The ¹³ C-NMR spectrum of the solution was measured.
(3) With the peak position of deuterated chloroform as 77 ppm, the peak area (A ₁ ) appearing at 46.2 to 46.6 ppm and the peak area (A ₂ ) appearing at 46.9 to 47.3 ppm of the spectrum, respectively Asked.
(4) Stereoregularity was calculated based on the following equation.
Threodiisotactic triad (%) = 100 A ₁ / (A ₁ + A ₂ )
Treodisindiotactic triad (%) = 100 A ₂ / (A ₁ + A ₂ )

Example 2
5.89 mg of chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,4,6-trimethylaniline-κN)] palladium (transition metal compound) To a 25 mL Schlenk tube containing 10.6 mg of sodium tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound), 0.5 mL of methylene chloride was added and stirred for 5 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 24 hours.
The number average molecular weight (Mn) of the obtained polymer is 9200, the molecular weight distribution (Mw / Mn) is 1.8, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 for the trans form. %, No stereoregularity was detected, and no glass transition point was detected in the range of −60 ° C. to 150 ° C. The obtained results are shown in Table 1.

Example 3
Chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2,6-diisopropylaniline-κN)] palladium (transition metal compound) 5.61 mg and sodium tetrakis (3,5-bistri To a 25 mL Schlenk tube containing 10.6 mg of fluoromethylphenyl) borate (boron compound), 0.5 mL of methylene chloride was added and stirred for 20 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 36 hours.
The number average molecular weight (Mn) of the obtained polymer is 6500, the molecular weight distribution (Mw / Mn) is 1.6, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. %, No stereoregularity was detected, and no glass transition point was detected in the range of −60 ° C. to 150 ° C. The obtained results are shown in Table 1.

Example 4
4.77 mg of chloro (methyl) [N, N ′-(butane-2,3-diylidene) bis (2,4,6-trimethylaniline-κN)] palladium (transition metal compound) and sodium tetrakis (3,5 -To a 25 mL Schlenk tube containing 10.6 mg of (bistrifluoromethylphenyl) borate (boron compound), 0.5 mL of methylene chloride was added and stirred for 20 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 24 hours.
The number average molecular weight (Mn) of the obtained polymer is 9800, the molecular weight distribution (Mw / Mn) is 1.6, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. The stereoregularity was 65% for threodicindiotactic triad, and no glass transition point was detected in the range of -60 ° C to 150 ° C. The obtained results are shown in Table 1.

Example 5
6.60 mg of chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,4,6-trimethylaniline-κN)] palladium (transition metal compound) To a 25 mL Schlenk tube containing 10.6 mg of sodium tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound), 0.5 mL of methylene chloride was added and stirred for 20 minutes. Thereafter, methylene chloride was distilled off, 0.5 mL of toluene and 0.156 g of isopropylidene diallyl malonate (monomer) were added, and the mixture was stirred at room temperature and polymerized for 48 hours.
The number average molecular weight (Mn) of the obtained polymer is 6000, the molecular weight distribution (Mw / Mn) is 1.6, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. %, No stereoregularity was detected, and no glass transition point was detected in the range of −60 ° C. to 150 ° C. The obtained results are shown in Table 1.

Example 6
6.60 mg of chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,4,6-trimethylaniline-κN)] palladium (transition metal compound) To a 25 mL Schlenk tube containing 10.6 mg of sodium tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound), 0.5 mL of methylene chloride was added and stirred for 10 minutes. Thereafter, methylene chloride was distilled off, 0.445 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 24 hours.
The number average molecular weight (Mn) of the obtained polymer is 18400, the molecular weight distribution (Mw / Mn) is 1.4, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. %, No stereoregularity was detected, and no glass transition point was detected in the range of −60 ° C. to 150 ° C. The obtained results are shown in Table 1.

Example 7
6.17 mg of chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2,6-diisopropylaniline-κN)] palladium (transition metal compound) and sodium To a 25 mL Schlenk tube containing 10.6 mg of tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound), 0.5 mL of methylene chloride was added and stirred for 20 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 24 hours.
The number average molecular weight (Mn) of the obtained polymer is 9000, the molecular weight distribution (Mw / Mn) is 1.6, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. The stereoregularity was 64% for threodicindiotactic triad, and no glass transition point was detected in the range of -60 ° C to 150 ° C. The obtained results are shown in Table 1.

Example 8
7.52 mg of chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis (2-isopropyl-6-phenylaniline-κN)] palladium (transition metal compound) To a 25 mL Schlenk tube containing 10.6 mg of sodium tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound), 0.5 mL of methylene chloride was added and stirred for 30 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 36 hours.
The number average molecular weight (Mn) of the obtained polymer is 6300, the molecular weight distribution (Mw / Mn) is 1.7, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. The stereoregularity was 68% for threodicindiotactic triad, and no glass transition point was detected in the range of -60 ° C to 150 ° C. The obtained results are shown in Table 1.

Example 9
Chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis {2,4-dimethyl-6- (2-methylphenyl) aniline-κN}] palladium (transition To a 25 mL Schlenk tube containing 7.25 mg of (metal compound) and 10.6 mg of sodium tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound), 0.25 mL of methylene chloride was added and stirred for 5 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 29 hours.
The number average molecular weight (Mn) of the obtained polymer is 8400, the molecular weight distribution (Mw / Mn) is 1.8, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. The stereoregularity was 66% for threoisotactic triad, and no glass transition point was detected in the range of -60 ° C to 150 ° C. The obtained results are shown in Table 1.

Example 10
Chloro (methyl) [N, N ′-(1,2-dihydroacenaphthylene-1,2-diylidene) bis {2,4-dimethyl-6- (1-naphthyl) aniline-κN}] palladium (transition metal Compound) 7.97 mg and sodium tetrakis (3,5-bistrifluoromethylphenyl) borate (boron compound) 10.6 mg were added to a 25 mL Schlenk tube, and 0.25 mL of methylene chloride was added and stirred for 5 minutes. Thereafter, 0.156 g of isopropylidene diallyl malonate (monomer) was added, and the mixture was stirred at room temperature and polymerized for 24 hours.
The number average molecular weight (Mn) of the obtained polymer is 4400, the molecular weight distribution (Mw / Mn) is 1.7, and the steric positional relationship between the main chain of the polymer and the 5-membered ring is 100 in the trans form. The stereoregularity was 83% for threoisotactic triad, and no glass transition point was detected in the range of -60 ° C to 150 ° C. The obtained results are shown in Table 1.

Claims (11)

A polymer comprising a repeating unit represented by the following formula (1).

(However, in the above formula (1), X ¹ , X ² , X ³ and X ⁴ each independently represent an atom of Group 16 of the periodic table of elements, and R ¹ and R ² each independently represent a hydrogen atom. Alternatively, it represents a hydrocarbon group having 1 to 20 carbon atoms, and R ¹ and R ² may be bonded to each other: A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ and A ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, disubstituted amino group, or hydrocarbon Represents a thio group.) The polymer according to claim 1, wherein the 5-membered ring in the repeating unit is a trans form represented by the following formula (2) with respect to the main chain of the polymer.

(However, in the above formula (2), X ¹ , X ² , X ³ and X ⁴ each independently represent an atom of Group 16 of the periodic table of elements, and R ¹ and R ² each independently represent a hydrogen atom. Alternatively, it represents a hydrocarbon group having 1 to 20 carbon atoms, and R ¹ and R ² may be bonded to each other: A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ and A ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, disubstituted amino group, or hydrocarbon Represents a thio group.)   A polymer according to claim 1 wherein the treodiisotactic triad is greater than 25%.   The polymer of claim 1, wherein the erythroisotactic triad is greater than 25%.   The polymer of claim 1 wherein the treodicindiotactic triad is greater than 25%.   2. A polymer according to claim 1, wherein the erythrosin syndiotactic triad is greater than 25%. A method for producing a polymer comprising a repeating unit represented by the following formula (1), comprising a step of polymerizing a compound represented by the following formula (3).

(However, in the above formulas (1) and (3), X ¹ , X ² , X ³ and X ⁴ each independently represent an atom of Group 16 of the periodic table of elements, and R ¹ and R ² are each independently Represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ¹ and R ² may be bonded to each other: A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , A ⁸ , A ⁹ and A ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, disubstituted amino group Or represents a hydrocarbon thio group.)   The method for producing a polymer according to claim 7, wherein the polymerization is carried out in the presence of a polymerization catalyst produced by contacting the transition metal compound with an organoaluminum compound and / or a boron compound. The method for producing a polymer according to claim 8, wherein the transition metal compound is a compound represented by the following formula [I].

(In the above formula [I], M represents a transition metal atom of Group 10 of the periodic table of elements, and R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group. Represents a substituted silyl group, an alkoxy group, an aralkyloxy group, or an aryloxy group, R ⁵ and R ⁶ each independently represent a hydrocarbon group having 1 to 30 carbon atoms, and R ⁷ and R ⁸ each independently Represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ⁷ and R ⁸ may be bonded to each other.) The method for producing a polymer according to claim 8, wherein the transition metal compound is a compound represented by the following formula [II].

(In the above formula [II], M represents a transition metal atom of Group 10 of the periodic table of elements, and R ³ and R ⁴ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group. , A substituted silyl group, an alkoxy group, an aralkyloxy group, or an aryloxy group, R ⁷ and R ⁸ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ⁷ and R ⁸ May be bonded to each other. R ⁹ and R ¹⁰ are each independently a hydrogen atom, halogen atom, alkyl group, aralkyl group, substituted silyl group, alkoxy group, aralkyloxy group, disubstituted amino group, or carbonized represents hydrogen thio group, R ¹¹ and R ¹² each independently represents an aryl group having 7 to 20 carbon atoms, each R ¹³ and R ¹⁴ are independently a hydrogen atom, a halogen atom Alkyl group, an aralkyl group, an aryl group, a substituted silyl group, alkoxy group, aralkyloxy group, aryloxy group, di-substituted amino group or a hydrocarbon thio group.) The method for producing a polymer according to claim 8, wherein the transition metal compound is a compound represented by the following formula [III].

(In the above formula [III], M represents a transition metal atom of Group 10 of the periodic table of elements, and R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group. , A substituted silyl group, an alkoxy group, an aralkyloxy group, or an aryloxy group, R ⁷ and R ⁸ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ⁷ and R ⁸ R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group having 6 carbon atoms, a substituted silyl group, alkoxy group, aralkyloxy group, an aryloxy group, an 2-substituted amino group or a hydrocarbon thio group,, R ¹⁹ and R ²⁰ are each independently a hydrogen atom, a halogen atom, alkyl Represents group, aralkyl group, aryl group, substituted silyl group, alkoxy group, aralkyloxy group, an aryloxy group, a disubstituted amino group or a hydrocarbon thio group.)