JP2022159184A - Metal complex, olefin-polymerization catalyst component and olefin-polymerization catalyst each comprising the metal complex, and method for producing olefin polymer using the olefin-polymerization catalyst - Google Patents

Abstract

To provide a novel metal complex that can yield a high-molecular-weight polypropylene polymer with high activity.SOLUTION: A metal complex is a product from a reaction between a compound represented by the following formula [I] or [II] with a transition metal compound comprising a transition metal belonging to Group 9, 10 or 11 in the periodic table. R5 and R6 independently represent an optionally substituted fused polycyclic hydrocarbon group. E1 is a phosphorus atom, an arsenic atom or an antimony atom. X1 is an oxygen atom, a sulfur atom or SO3. In formula [I], Z is a hydrogen atom or a leaving group, m is a valence of Z.SELECTED DRAWING: None

Description

The present invention provides a metal complex useful for the production of olefin polymers and copolymers, an olefin polymerization catalyst component and an olefin polymerization catalyst using the metal complex, and an olefin polymerization catalyst using the olefin polymerization catalyst. It relates to a method for producing a polymer.

Copolymers of olefins and polar group-containing monomers are industrially useful polymers. A high-pressure radical method is usually used to obtain this copolymer by direct polymerization. However, this method has the disadvantage that propylene and higher α-olefins cannot be polymerized.
It is industrially difficult to obtain a copolymer by any method other than the high-pressure radical method, and catalyst deactivation was unavoidable when a Ziegler catalyst or metallocene catalyst was used.

After that, in metallocene catalysts, it became possible to copolymerize ethylene and methyl methacrylate with organic rare earth metal complex metallocene catalysts, and after the 1990s, copolymerization of ethylene and polar group-containing comonomers with late transition metal complex catalysts became possible. is being intensively studied. For example, the (α-diimine) palladium complex reported by Brookhart et al. (see Non-Patent Document 1) and the (salicylamidinate) nickel catalyst reported by Grubbs et al. (See Non-Patent Document 2) are known. . When these catalysts are used, the polymerization temperature is lowered in order to suppress the frequent occurrence of chain transfer, so the productivity of the copolymer is generally low and the molecular weight is also low.

In recent years, in the copolymerization of ethylene and a polar group-containing monomer, the above-mentioned problems are the (phosphorus sulfonate) palladium complex (see Patent Document 1) and the so-called SHOP catalyst, which has phosphorus and oxygen as coordinating atoms. This has been overcome by discoveries such as (phosphorous phenolate)nickel complexes (see US Pat.
Thus, the (phosphorous phenolate)nickel complex was useful as a copolymerization catalyst for ethylene and a polar group-containing monomer, but it was not active for the polymerization of olefins, especially propylene, and for the copolymerization of propylene and a polar group-containing monomer. There is still room for improvement from the viewpoint of molecular weight and molecular weight.

Further, a catalyst is disclosed in which a phosphinosulfonic acid ligand having a fluorenyl group on phosphorus and a palladium(0) compound are combined (see Patent Documents 5 and 6).
Although it is shown that the palladium complex is also useful as a catalyst for copolymerization of ethylene and a polar group-containing monomer, it is not disclosed that propylene polymerization or copolymerization of propylene and a polar group-containing monomer proceeds. However, there still remains room for improvement from the viewpoint of increasing the molecular weight of olefins, especially propylene.

JP 2010-150246 A WO2010/050256 U.S. Pat. No. 6,559,326 Japanese Patent Application Laid-Open No. 2005-307021 WO2020/175482 Japanese Unexamined Patent Application Publication No. 2020-164828

M. Brookhart et al. , "J. Am. Chem. Soc.", 1996, 118, 267-268. R. H. Grubbs et al. , "Science", 2000, 287, 460-462. J. Heinicke et al. , "Chem. Eur. J.", 2003, 9, 6093-6107. J. Heinicke et al. , "European Journal of Inorganic Chemistry", 2000, 3, 431-440.

In view of the above-mentioned problems of the prior art, the object of the present invention is to provide a novel metal complex, a catalyst component, a novel metal complex that gives a polymer with high activity and a higher molecular weight, which is used for the production of olefins, especially propylene polymers and copolymers. and to provide a method for producing olefins, especially propylene polymers and copolymers using the same.

As a result of intensive studies to solve the above problems, the present inventors have found a compound represented by the general formula [I] or [II], which has two condensed polycyclic rings on E ¹ capable of reacting with a transition metal. Reaction formation of a ligand having a hydrocarbon group of the formula and having a specific substituent at the ortho position (R ¹ ) of X ¹ capable of reacting with a transition metal, and a transition metal compound of groups 9 to 11 of the periodic table Using the novel metal complexes as catalyst components, the polymerization of olefins, especially propylene, proceeds with high activity and compared to ligands with ^one condensed polycyclic hydrocarbon group on E1, the molecular weight has been found to be remarkably improved, and the present invention has been completed.

That is, one embodiment of the present invention is a reaction of a compound represented by the following general formula [I] or [II] with a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table The product, the metal complex, is provided.

［式［Ｉ］および［ＩＩ］中のＲ^１～Ｒ^６、Ｅ^１、およびＸ^１は以下の通りである。
Ｒ^１は、炭素数１～３０の直鎖状アルキル基、炭素数３～３０の分岐した非環状アルキル基、炭素数２～３０のアルケニル基、炭素数３～３０の側鎖を有していてもよいシクロアルキル基、炭素数６～３０のアリール基、炭素数７～３０のアリールアルキル基、または炭素数７～３０のアルキルアリール基を表す。
Ｒ^２、Ｒ^３およびＲ^４は、それぞれ独立に、下記（ｉ）～（ｉｖ）からなる群より選ばれる原子または基を表す。
（ｉ）水素原子
（ｉｉ）ハロゲン原子
（ｉｉｉ）ヘテロ原子およびヘテロ原子を含有する基からなる群より選ばれる基を有していてもよい、炭素数１～３０の直鎖状アルキル基、炭素数３～３０の分岐した非環状アルキル基、炭素数２～３０のアルケニル基、炭素数３～３０の側鎖を有していてもよいシクロアルキル基、炭素数６～３０のアリール基、炭素数７～３０のアリールアルキル基、または炭素数７～３０のアルキルアリール基
（ｉｖ）ＯＲ^９、ＣＯ_２Ｒ^９、ＣＯ_２Ｍ’、Ｃ（Ｏ）Ｎ（Ｒ^８）_２、Ｃ（Ｏ）Ｒ^９、ＯＣ（Ｏ）Ｒ^９、ＳＲ^９、ＳＯ_２Ｒ^９、ＳＯＲ^９、ＯＳＯ_２Ｒ^９、Ｐ（Ｏ）（ＯＲ^９）_２－ｙ（Ｒ^８）_ｙ、ＣＮ、ＮＨＲ^９、Ｎ（Ｒ^９）_２、Ｓｉ（ＯＲ^８）_３－ｘ（Ｒ^８）_ｘ、ＯＳｉ（ＯＲ^８）_３－ｘ（Ｒ^８）_ｘ、ＮＯ_２、ＳＯ_３Ｍ’、ＰＯ_３Ｍ’_２、Ｐ（Ｏ）（ＯＲ^８）_２Ｍ’、またはエポキシ含有基。ここで、Ｒ^８は水素原子または炭素数１～２０の炭化水素基を表す。また、Ｒ^９は炭素数１～２０の炭化水素基を表す。Ｍ’は、アルカリ金属、アルカリ土類金属、アンモニウム、４級アンモニウムまたはホスホニウムを表し、ｘは０から３までの整数、ｙは０から２までの整数を表す。
Ｒ^２、Ｒ^３およびＲ^４は隣接置換基同士が互いに連結し、脂環式環、芳香族環、または酸素原子、窒素原子および硫黄原子からなる群より選ばれるヘテロ原子を含有する複素環を形成してもよい。このとき、環員数は５～８であり、該環上に置換基を有していても、有していなくてもよい。
Ｒ^５またはＲ^６は、それぞれ独立に、置換基を有していてもよい縮合多環式炭化水素基を表す。
Ｅ^１は、リン原子、砒素原子またはアンチモン原子を表す。
Ｘ^１は、酸素原子、硫黄原子またはＳＯ_３を表す。
また、一般式［Ｉ］中、
Ｚは、水素原子、または脱離基を表し、
ｍはＺの価数を表す。］

[R ¹ to R ⁶ , E ¹ and X ¹ in formulas [I] and [II] are as follows.
R ¹ has a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a side chain having 3 to 30 carbon atoms. may be a cycloalkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms.
R ² , R ³ and R ⁴ each independently represent an atom or group selected from the group consisting of (i) to (iv) below.
(i) a hydrogen atom (ii) a halogen atom (iii) a linear alkyl group having 1 to 30 carbon atoms, optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom, carbon a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, carbon an arylalkyl group having 7 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms (iv) OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O )(OR ⁸ ) ₂ M′, or an epoxy-containing group. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;
Adjacent substituents of R ² , R ³ and R ⁴ are connected to each other and represent an alicyclic ring, an aromatic ring, or a heterocyclic ring containing a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. may be formed. At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.
^R5 or ^R6 each independently represents a condensed polycyclic hydrocarbon group which may have a substituent.
E ¹ represents a phosphorus atom, an arsenic atom or an antimony atom.
X1 represents ^an oxygen atom _, a sulfur atom or SO3.
Further, in general formula [I],
Z represents a hydrogen atom or a leaving group,
m represents the valence of Z; ]

One embodiment of the present invention provides a metal complex represented by general formula [III] below.

［一般式［ＩＩＩ］中、Ｒ^１～Ｒ^６、Ｅ^１、およびＸ^１は前記と同様である。
Ｍは、周期表の９族、１０族または１１族に属する遷移金属原子を表す。
Ｒ^７は、水素原子、ヘテロ原子を含有していてもよい炭素数１～２０の炭化水素基、またはＭに配位したリガンドを表す。
Ｌ^１は、Ｍに配位したリガンドを表す。
Ｒ^７とＬ^１が互いに結合して環を形成してもよい。］

[In general formula [III], R ¹ to R ⁶ , E ¹ and X ¹ are the same as above.
M represents a transition metal atom belonging to group 9, 10 or 11 of the periodic table.
R ⁷ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom, or a ligand coordinated to M;
L ¹ represents the ligand coordinated to M;
R ⁷ and L ¹ may combine with each other to form a ring. ]

Another embodiment of the present invention provides an olefin polymerization catalyst component comprising the metal complex of the present invention.

Another embodiment of the present invention provides an olefin polymerization catalyst comprising the olefin polymerization catalyst component of the present invention.

Another embodiment of the present invention is reaction production of a compound represented by the following general formula [I] or [II] with a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table Provided are catalysts for the polymerization of olefins, comprising:

［式［Ｉ］および［ＩＩ］中のＲ^１～Ｒ^６、Ｅ^１、およびＸ^１は前記と同様である。
また、一般式［Ｉ］中のＺおとびｍは前記と同様である］

[R ¹ to R ⁶ , E ¹ and X ¹ in formulas [I] and [II] are the same as above.
In addition, Z and m in the general formula [I] are the same as described above]

In the metal complex, the catalyst component for olefin polymerization, and the catalyst for olefin polymerization of the present invention, the transition metal compound contains a transition metal belonging to Group 10 of the periodic table in order to give a highly active polymer having a high molecular weight. can be anything.

In the metal complex, the catalyst component for olefin polymerization, and the catalyst for olefin polymerization of the present invention, each of R ⁵ and R ⁶ independently has a substituent in order to give a highly active polymer having a high molecular weight. may be a condensed polycyclic hydrocarbon group formed by condensing three or more rings that may be

In the metal complex, the catalyst component for olefin polymerization, and the catalyst for olefin polymerization of the present invention, each of R ⁵ and R ⁶ independently has a substituent in order to give a highly active polymer having a high molecular weight. may be a fluorenyl group or a 9,10-dihydroanthracenyl group.

In the metal complex, olefin polymerization catalyst component, and olefin polymerization catalyst of the present invention, R ¹ is an aryl group having 6 to 30 carbon atoms or It may be ˜30 alkylaryl groups.

In the metal complex, the catalyst component for olefin polymerization, and the catalyst for olefin polymerization of the present invention, R ¹ is a substituent represented by the following general formula (1) in order to give a highly active polymer having a high molecular weight. It can be.

（前記一般式（１）において、Ｒ^ａはそれぞれ独立に、炭素数が２以上の直鎖状若しくは分岐した非環状アルキル基を表し、Ｒ^ｂはそれぞれ独立に、水素原子、又は直鎖状若しくは分岐した非環状アルキル基を表し、＊は結合手を表す。）

(In the general formula (1), each R ^a independently represents a linear or branched non-cyclic alkyl group having 2 or more carbon atoms, and each R ^b independently represents a hydrogen atom, or a linear or represents a branched acyclic alkyl group, and * represents a bond.)

In the metal complex, the catalyst component for olefin polymerization, and the catalyst for olefin polymerization of the present invention, R ¹ may be a 2,6-diisopropylphenyl group from the viewpoint of providing a highly active polymer having a high molecular weight.

In the metal complex, olefin polymerization catalyst component, and olefin polymerization catalyst of the present invention, the transition metal compound contains a nickel atom or a palladium atom in order to give a highly active polymer having a high molecular weight. good.

In the metal complex, the catalyst component for olefin polymerization, and the catalyst for olefin polymerization of the present invention, E1 may be ^a phosphorus atom from the viewpoint of providing a highly active polymer having a high molecular weight.
Moreover, in the metal complex of the present invention, X ¹ may be an oxygen atom from the viewpoint of providing a highly active polymer having a high molecular weight.

The olefin polymerization catalyst of the present invention may further contain the following component (B).
Component (B): an organoaluminum compound.

Another embodiment of the present invention provides a method for producing an olefin polymer, comprising polymerizing or copolymerizing an olefin in the presence of the olefin polymerization catalyst of the present invention.
In the method for producing an olefin polymer of the present invention, the olefin may be propylene.

According to the present invention, novel metal complexes, catalyst components, and olefins, especially propylene, using the same, which give polymers with high activity and higher molecular weights, for use in the production of olefins, especially propylene polymers and copolymers Methods of making polymers and copolymers can be provided.

The present invention provides a compound represented by the general formula [I] or [II] and 9 of the periodic table such as Ni (nickel), Pd (palladium), Co (cobalt), Cu (copper) or Rh (rhodium). a metal complex which is a reaction product with a transition metal compound containing a transition metal belonging to Group 10 or 11, a metal complex represented by the general formula [III], an olefin polymerization catalyst component containing these metal complexes, and a catalyst comprising the same as a catalyst component, and a method for producing an olefin polymer or copolymer in the presence of the catalyst.
In the present invention, "polymerization" is a general term for homopolymerization of one type of monomer and copolymerization of a plurality of types of monomers. ”. Moreover, in the present invention, "(meth)acrylic acid ester" includes both acrylic acid ester and methacrylic acid ester.
Also, in this specification, the term "to" indicating a numerical range is used to include the numerical values before and after it as lower and upper limits.

1. Metal Complex The metal complex of the present invention is produced by reacting a compound represented by the following general formula [I] or [II] with a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table. It is a thing.

［式［Ｉ］および［ＩＩ］中のＲ^１～Ｒ^６、Ｅ^１、およびＸ^１は以下の通りである。
Ｒ^１は、炭素数１～３０の直鎖状アルキル基、炭素数３～３０の分岐した非環状アルキル基、炭素数２～３０のアルケニル基、炭素数３～３０の側鎖を有していてもよいシクロアルキル基、炭素数６～３０のアリール基、炭素数７～３０のアリールアルキル基、または炭素数７～３０のアルキルアリール基を表す。
Ｒ^２、Ｒ^３およびＲ^４は、それぞれ独立に、下記（ｉ）～（ｉｖ）からなる群より選ばれる原子または基を表す。
（ｉ）水素原子
（ｉｉ）ハロゲン原子
（ｉｉｉ）ヘテロ原子およびヘテロ原子を含有する基からなる群より選ばれる基を有していてもよい、炭素数１～３０の直鎖状アルキル基、炭素数３～３０の分岐した非環状アルキル基、炭素数２～３０のアルケニル基、炭素数３～３０の側鎖を有していてもよいシクロアルキル基、炭素数６～３０のアリール基、炭素数７～３０のアリールアルキル基、または炭素数７～３０のアルキルアリール基
（ｉｖ）ＯＲ^９、ＣＯ_２Ｒ^９、ＣＯ_２Ｍ’、Ｃ（Ｏ）Ｎ（Ｒ^８）_２、Ｃ（Ｏ）Ｒ^９、ＯＣ（Ｏ）Ｒ^９、ＳＲ^９、ＳＯ_２Ｒ^９、ＳＯＲ^９、ＯＳＯ_２Ｒ^９、Ｐ（Ｏ）（ＯＲ^９）_２－ｙ（Ｒ^８）_ｙ、ＣＮ、ＮＨＲ^９、Ｎ（Ｒ^９）_２、Ｓｉ（ＯＲ^８）_３－ｘ（Ｒ^８）_ｘ、ＯＳｉ（ＯＲ^８）_３－ｘ（Ｒ^８）_ｘ、ＮＯ_２、ＳＯ_３Ｍ’、ＰＯ_３Ｍ’_２、Ｐ（Ｏ）（ＯＲ^８）_２Ｍ’、またはエポキシ含有基。ここで、Ｒ^８は水素原子または炭素数１～２０の炭化水素基を表す。また、Ｒ^９は炭素数１～２０の炭化水素基を表す。Ｍ’は、アルカリ金属、アルカリ土類金属、アンモニウム、４級アンモニウムまたはホスホニウムを表し、ｘは０から３までの整数、ｙは０から２までの整数を表す。
Ｒ^２、Ｒ^３およびＲ^４は隣接置換基同士が互いに連結し、脂環式環、芳香族環、または酸素原子、窒素原子および硫黄原子からなる群より選ばれるヘテロ原子を含有する複素環を形成してもよい。このとき、環員数は５～８であり、該環上に置換基を有していても、有していなくてもよい。
Ｒ^５またはＲ^６は、それぞれ独立に、置換基を有していてもよい縮合多環式炭化水素基を表す。
Ｅ^１は、リン原子、砒素原子またはアンチモン原子を表す。
Ｘ^１は、酸素原子、硫黄原子またはＳＯ_３を表す。
また、一般式［Ｉ］中、
Ｚは、水素原子、または脱離基を表し、
ｍはＺの価数を表す。］

[R ¹ to R ⁶ , E ¹ and X ¹ in formulas [I] and [II] are as follows.
R ¹ has a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a side chain having 3 to 30 carbon atoms. may be a cycloalkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms.
R ² , R ³ and R ⁴ each independently represent an atom or group selected from the group consisting of (i) to (iv) below.
(i) a hydrogen atom (ii) a halogen atom (iii) a linear alkyl group having 1 to 30 carbon atoms, optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom, carbon a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, carbon an arylalkyl group having 7 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms (iv) OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O )(OR ⁸ ) ₂ M′, or an epoxy-containing group. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;
Adjacent substituents of R ² , R ³ and R ⁴ are connected to each other and represent an alicyclic ring, an aromatic ring, or a heterocyclic ring containing a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. may be formed. At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.
^R5 or ^R6 each independently represents a condensed polycyclic hydrocarbon group which may have a substituent.
E ¹ represents a phosphorus atom, an arsenic atom or an antimony atom.
X1 represents ^an oxygen atom _, a sulfur atom or SO3.
Further, in general formula [I],
Z represents a hydrogen atom or a leaving group,
m represents the valence of Z; ]

The reaction product of the compound represented by the general formula [I] or [II], which is the metal complex of the present invention, and the transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table, For example, it can be obtained by contacting the compound represented by the general formula [I] or [II] with a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table.
In the present invention, “contact” means that E ¹ in the general formula [I] or [II] can form a coordinate bond with the transition metal, and/or X ¹ in these general formulas can form a coordinate bond with the above It means that the compound represented by the general formula [I] or [II] and the transition metal compound are sufficiently close to form a single bond with the transition metal. And, contacting the compound represented by the general formula [I] or [II] with the transition metal compound means that these compounds are present in sufficient proximity such that at least one of the two types of bonds is It means to mix these compounds so that they can be formed.
Conditions for mixing the compound represented by the general formula [I] or [II] and the transition metal compound are not particularly limited. These compounds may be mixed directly or may be mixed using a solvent. In particular, from the viewpoint of achieving uniform mixing, it is preferable to use a solvent.
In the obtained metal complex, the compound represented by the general formula [I] or [II] becomes a ligand, so that the compound represented by the general formula [I] or [II] and the transition metal A reaction with a compound usually becomes a ligand exchange reaction. When the obtained metal complex is thermodynamically more stable than the transition metal compound, the compound represented by the general formula [I] or [II] and the transition metal compound are heated at room temperature (15 to 30° C. ), the ligand exchange reaction proceeds. On the other hand, when the obtained metal complex is thermodynamically less stable than the transition metal compound, it is preferable to heat the mixture appropriately in order to allow the ligand exchange reaction to proceed sufficiently.

As a metal complex obtained by contacting a compound represented by the general formula [I] or [II] with a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table, It is presumed to have a structure represented by the general formula [III].
However, since the compound represented by the general formula [I] or [II] is a bidentate ligand, the compound is a transition metal compound containing a transition metal belonging to group 9, 10 or 11 of the periodic table. , a metal complex having a structure other than the structure represented by the general formula [III] may be produced. For example, it is conceivable that only X1 in general formula [ ^I ] or [II] forms a bond with a transition metal, or ^only E1 in these formulas forms a bond with a transition metal. Further, the metal complex represented by the general formula [III] is a 1:1 reaction product of the compound represented by the general formula [I] or [II] and the transition metal compound. may result in reaction products with different composition ratios. For example, two or more molecules of the compound represented by general formula [I] or [II] may form a complex with one transition metal, or A compound molecule may react with two or more transition metals to form a polynuclear complex.
Therefore, the metal complex of the present invention may be a mixture containing two or more reaction products, or may be a metal complex composition.
In the present invention, a metal complex having a structure other than the structure represented by the general formula [III] is used in the production of an olefin (co)polymer in the same manner as the metal complex represented by the general formula [III]. It does not deny that it can be used for

By using the metal complex of the present invention, an olefin (co)polymer with a higher molecular weight, especially a propylene (co)polymer with a higher molecular weight, can be obtained with high activity.
A specific hydrocarbon having two bulky condensed polycyclic hydrocarbon groups on E ¹ capable of reacting with the central metal M and at the ortho position (R ¹ ) of bulky X ¹ capable of reacting with a transition metal Since it has a group, the degree of steric crowding around the central metal M is appropriately controlled, which is thought to suppress β-hydrogen elimination and increase the molecular weight of the resulting polymer chain.
Due to these synergistic effects, it is presumed that the use of the metal complex of the present invention makes it possible to obtain olefin (co)polymers with higher activity and higher molecular weight.

R ¹ to R ⁶ , E ¹ and X ¹ in general formulas [I] and [II], and Z and m in general formula [I] are described below.
R ¹ has a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a side chain having 3 to 30 carbon atoms. may be a cycloalkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms.
The upper limit of each carbon number of the linear alkyl group, the branched acyclic alkyl group, the alkenyl group, the cycloalkyl group optionally having a side chain, the aryl group, the arylalkyl group, and the alkylaryl group is preferably is 25, more preferably 20, and even more preferably 15.

Examples of R ¹ include straight-chain alkyl groups having 1 to 30 carbon atoms, such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n linear alkyl groups having 1 to 10 carbon atoms such as -heptyl group, n-octyl group, n-nonyl group and n-decyl group;
Examples of R ¹ include branched acyclic alkyl groups having 3 to 30 carbon atoms, such as isopropyl group, isobutyl group, tert-butyl group (t-butyl group), sec-butyl group, isopentyl group (3 -methylbutyl group), t-pentyl group (1,1-dimethylpropyl group), sec-pentyl group (1-methylbutyl group), 2-methylbutyl group, neopentyl group (2,2-dimethylpropyl group), 1,2 -Dimethylpropyl group, isohexyl group (4-methylpentyl group) and other branched acyclic alkyl groups having 3 to 10 carbon atoms, and may be branched acyclic alkyl groups having 3 to 8 carbon atoms.
Examples of R ¹ include alkenyl groups having 2 to 30 carbon atoms, such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, styryl group, cinnamyl group, allyl group, butenyl group, It may be an alkenyl group having 3 to 8 carbon atoms such as pentenyl group, hexenyl group or styryl group, or an alkenyl group having 4 to 8 carbon atoms such as butenyl group, pentenyl group, hexenyl group or styryl group.

Among examples of R ¹ , the cycloalkyl group optionally having a side chain having 3 to 30 carbon atoms includes, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 2-methylcyclopentyl group, and a 3-methylcyclopentyl group. cyclohexyl group, 4-methylcyclohexyl group, 4-ethylcyclohexyl group, cyclooctyl group, decahydronaphthyl group (bicyclo[4,4,0]decyl group), etc. may be a cycloalkyl group having 3 to 6 carbon atoms and optionally having a side chain.
Among examples of R ¹ , aryl groups having 6 to 30 carbon atoms include phenyl, naphthyl, azulenyl, biphenyl, anthracenyl, terphenyl, phenanthrenyl, triphenylenyl, chrysenyl and pyrenyl groups. , a tetracenyl group and the like, and may be an aryl group having 6 to 12 carbon atoms.
Examples of R ¹ include arylalkyl groups having 7 to 30 carbon atoms, such as benzyl group, phenethyl group (2-phenylethyl group), 9-fluorenyl group, naphthylmethyl group, 1-tetralinyl group and the like. Examples include arylalkyl groups having 7 to 15 carbon atoms, and may be arylalkyl groups having 7 to 10 carbon atoms.

Among examples of R ¹ , the alkylaryl group having 7 to 30 carbon atoms may be an aryl group substituted with one or more linear or branched acyclic alkyl groups having 1 to 10 carbon atoms. an alkylaryl group in which the aryl group having 6 to 18 carbon atoms is substituted with at least one of the linear alkyl group having 1 to 10 carbon atoms and the branched acyclic alkyl group having 3 to 10 carbon atoms; and at least two of the straight-chain alkyl group having 1 to 10 carbon atoms and the branched acyclic alkyl group having 3 to 10 carbon atoms are substituted on the aryl group having 6 to 18 carbon atoms. It may be an alkylaryl group. Specific examples of alkylaryl groups having 7 to 30 carbon atoms include tolyl, xylyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl and octylphenyl groups. , a nonylphenyl group, a decylphenyl group, an undecylphenyl group, a dodecylphenyl group, and other alkylaryl groups having 7 to 20 carbon atoms.

R ¹ is preferably a cycloalkyl group optionally having a side chain having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or An arylalkyl group having 7 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms can be mentioned, more preferably an aryl group having 6 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms, more preferably an arylalkyl group having 7 to 30 carbon atoms. includes an alkylaryl group having 7 to 30 carbon atoms.

R ¹ is preferably at least one of the linear alkyl group having 1 to 10 carbon atoms and the branched acyclic alkyl group having 3 to 10 carbon atoms, from the viewpoint of giving a highly active polymer having a high molecular weight. One or more species include an alkylaryl group substituted with the aryl group having 6 to 12 carbon atoms, more preferably the linear alkyl group having 1 to 10 carbon atoms and the branched alkyl group having 3 to 10 carbon atoms. At least one of the acyclic alkyl groups is two or more, and an alkylaryl group in which the aryl group having 6 to 12 carbon atoms is substituted, more preferably a substituent represented by the following general formula (1) mentioned.

（前記一般式（１）において、Ｒ^ａはそれぞれ独立に、炭素数が２以上の直鎖状若しくは分岐した非環状アルキル基を表し、Ｒ^ｂはそれぞれ独立に、水素原子、又は直鎖状若しくは分岐した非環状アルキル基を表し、＊は結合手を表す。）

(In the general formula (1), each R ^a independently represents a linear or branched non-cyclic alkyl group having 2 or more carbon atoms, and each R ^b independently represents a hydrogen atom, or a linear or represents a branched acyclic alkyl group, and * represents a bond.)

In general formula (1), the linear or branched non-cyclic alkyl group having 2 or more carbon atoms in R ^a is a linear or branched non-cyclic alkyl group having 2 or more and 10 or less carbon atoms, Often, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group and the like having 2 to 2 carbon atoms 10 linear alkyl groups, isopropyl group, isobutyl group, tert-butyl group (t-butyl group), sec-butyl group, isopentyl group (3-methylbutyl group), t-pentyl group (1,1-dimethylpropyl group), sec-pentyl group (1-methylbutyl group), 2-methylbutyl group, neopentyl group (2,2-dimethylpropyl group), 1,2-dimethylpropyl group, isohexyl group (4-methylpentyl group), etc. A branched non-cyclic alkyl group having 3 to 10 carbon atoms can be mentioned.
In general formula (1), the linear or branched non-cyclic alkyl group for R ^b may be ^a linear or branched non-cyclic alkyl group having 1 or more and 10 or less carbon atoms. In addition to the alkyl group, it may be a methyl group.

Substituents represented by general formula (1) for R ¹ include, for example, a 2,6-diethylphenyl group, a 2,6-di-n-propylphenyl group, and a 2,6-di-n-butylphenyl group. , 2,6-di-n-pentylphenyl group, 2,6-di-n-hexylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,6-di-t-butyl phenyl group, 2,6-di-sec-butylphenyl group, 2,6-diisopentylphenyl group, 2,6-di-t-pentylphenyl group, 2,6-di-sec-pentyl group phenyl group, 2,4,6-triethylphenyl group, 2,4,6-tri-n-propylphenyl group, 2,4,6-tri-isopropylphenyl group, 2,4,6-tri-n-butylphenyl group, etc. are mentioned.
Among these, more preferred are a 2,6-diisopropylphenyl group, a 2,6-di-t-butylphenyl group and the like, and it is more preferred that R ¹ is a 2,6-diisopropylphenyl group. .

R ² , R ³ and R ⁴ each independently represent an atom or group selected from the group consisting of (i) to (iv) below.
(i) a hydrogen atom (ii) a halogen atom (iii) a linear alkyl group having 1 to 30 carbon atoms, optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom, carbon a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, carbon an arylalkyl group having 7 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms (iv) OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O )(OR ⁸ ) ₂ M′, or an epoxy-containing group. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;
Adjacent substituents of R ² , R ³ and R ⁴ are connected to each other and represent an alicyclic ring, an aromatic ring, or a heterocyclic ring containing a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. may be formed. At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.

(ii) Halogen atoms include fluorine, chlorine, bromine and iodine atoms. Among these, a fluorine atom is preferred.

Heteroatoms used in (iii) include oxygen, nitrogen, phosphorus, sulfur, selenium, silicon, halogen and boron atoms. Among these hetero atoms, a fluorine atom and a chlorine atom are preferred.
Specific examples of the "heteroatom-containing group" used in (iii) include the same groups as the heteroatom-containing substituent (iv) described below. Examples of the “heteroatom-containing group” include an alkoxy group (OR ⁹ ), an ester group (CO ₂ R ⁹ ), and the like.
^In addition, R9 is as described later.
In (iii) above, the total carbon number of the substituents corresponding to R ² to R ⁴ is preferably 1-30, more preferably 2-25, still more preferably 4-20.
Based on the above, (iii) “a specific group optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom” refers to (iii-A) a straight group having 1 to 30 carbon atoms chain alkyl group, branched acyclic alkyl group having 3 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, 6 to 6 carbon atoms 30 aryl groups, arylalkyl groups having 7 to 30 carbon atoms, and alkylaryl groups having 7 to 30 carbon atoms, (iii-B) each group of (iii-A) has 1 or more heteroatoms. a substituted group, (iii-C) a group in which each group of (iii-A) is substituted with one or more of the above "heteroatom-containing groups", and (iii-D) the above Each group of (iii-A) is substituted with one or more heteroatoms and is substituted with one or more heteroatom-containing groups. (iii-C) includes, for example, an alkyl group substituted with an alkoxy group, an aryl group substituted with an ester group, and the like.

(iv) heteroatom-containing substituents are specifically OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O)R ⁹ , OC(O ) R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N(R ⁹ ) ₂ , Si (OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O)(OR ⁸ ) ₂ M', and refers to epoxy-containing groups. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. In the present invention, the hydrocarbon group includes saturated and unsaturated aliphatic hydrocarbons and aromatic hydrocarbons, and the hydrocarbon group having 1 to 20 carbon atoms includes the linear alkyl group and branched acyclic hydrocarbon group. Among alkyl groups, alkenyl groups, cycloalkyl groups which may have a side chain, aryl groups, arylalkyl groups, or alkylaryl groups, those having 1 to 20 carbon atoms can be mentioned. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;

R ² , R ³ and R ⁴ are each independently preferably (i) a hydrogen atom; (ii) a fluorine atom, a chlorine atom or a bromine atom; (iii) a methyl group, an ethyl group, an isopropyl group or a butyl group , phenyl group, trifluoromethyl group, pentafluorophenyl group, naphthyl group, anthracenyl group; (iv) methoxy group, ethoxy group, phenoxy group, nitrile group, trimethylsilyl group, triethylsilyl group, dimethylphenylsilyl group, trimethoxysilyl group, triethoxysilyl group, trimethylsilyloxy group, trimethoxysiloxy group, cyclohexylamino group, sodium sulfonate, potassium sulfonate, sodium phosphate, potassium phosphate and the like.
Among these, particularly preferred are (i) hydrogen atom; (iii) methyl group, isobutyl group, tert-butyl group (t-butyl group), sec-butyl group, pentafluorophenyl group; (iv) methoxy group, trimethylsilyl group, trimethylsilyloxy group, cyclohexylamino group and the like. ^In particular, R ³ is preferably a hydrogen atom, a methyl group or a t-butyl group, and more preferably a hydrogen atom or a t-butyl group.

Adjacent substituents of R ² , R ³ and R ⁴ are linked to each other to form an alicyclic ring, an aromatic ring, or a hetero ring containing a hetero atom selected from the group consisting of oxygen, nitrogen and sulfur. You may At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.
In addition, multiple groups contained within R ² may be linked together to form a ring on R ² . The same applies when either R ³ or R ⁴ contains multiple groups.

R5 and ^R6 each independently represent an ^optionally substituted condensed polycyclic hydrocarbon group.
Examples of the condensed polycyclic hydrocarbon group include, for example, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a condensed polycyclic hydrocarbon group formed by condensing two rings such as a heptalenyl group; a biphenylenyl group, an as- Condensed polycyclic hydrocarbon groups formed by condensing three rings such as indacenyl group, s-indacenyl group, acenaphthylenyl group, fluorenyl group, phenalenyl group, phenanthryl group, anthracenyl group, 9,10-dihydroanthracenyl group; A condensed polycyclic hydrocarbon group formed by condensing four rings such as a fluoranthenyl group, an acephenanthrylene group, an aceanthrilenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, and a preadenyl group; Condensed polycyclic hydrocarbon groups in which five rings are condensed, such as picenyl group, perylenyl group, pentaphenyl group, pentacenyl group and tetraphenylenyl group.
The condensed polycyclic hydrocarbon group is preferably a condensed polycyclic hydrocarbon group in which three or more rings are condensed from the viewpoint of giving a polymer having high activity and a high molecular weight, and three rings are condensed. More preferably, at least one of a fluorenyl group, as-indacenyl group, s-indacenyl group, phenanthryl group, anthracenyl group and 9,10-dihydroanthracenyl group is preferred, and fluorenyl or 9,10-dihydroanthracenyl groups are even more preferred.

Each of the condensed polycyclic hydrocarbon groups may have a substituent. Examples of this substituent may be an atom or group selected from the group consisting of (ii) to (iv) above, and include a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, and a carbon atom substituted with a halogen atom. a hydrocarbon group having 1 to 10 carbon atoms, a hydrocarbon group having 2 to 20 carbon atoms substituted by an alkoxy group having 1 to 10 carbon atoms, a hydrocarbon group having 7 to 20 carbon atoms substituted by an aryloxy group having 6 to 10 carbon atoms; It may be a substituent selected from the group consisting of a hydrocarbon group, an alkoxy group having 1 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms. The hydrocarbon group here may be the same as described above.
The substituents of the condensed polycyclic hydrocarbon group are preferably fluorine atom, chlorine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, t-pentyl group, benzyl group, phenyl group; trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group; methoxy group, ethoxy group, 1-propoxy group, isopropoxy group, 1-butoxy group , isobutoxy group, sec-butoxy group, t-butoxy group, pentyloxy group, methoxymethyl group, 2-methoxyethyl group, isopropoxymethyl group, 2-isopropoxyethyl group, 2-methoxyphenyl group, 3-methoxyphenyl group , 4-methoxyphenyl group; phenoxymethyl group, 2-phenoxyethyl group, 2-phenoxyphenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group; methoxy group, ethoxy group, 1-propoxy group, isopropoxy group, 1-butoxy group, isobutoxy group, sec-butoxy group, t-butoxy group, pentyloxy group; phenoxy group, 1-naphthoxy group, 2-naphthoxy group and the like.

R ⁵ and R ⁶ are each independently preferably an optionally substituted fluorenyl group or an optionally substituted 9,10 from the viewpoint of giving a polymer with high activity and high molecular weight. -dihydroanthracenyl group, preferably a substituent represented by the following general formula (2) or (3).

（前記一般式（２）において、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、Ｒ^ｇ、Ｒ^ｈ、Ｒ^ｉ、及びＲ^ｊはそれぞれ独立に、水素原子、ハロゲン原子、炭素数１～１０の炭化水素基、ハロゲン原子で置換された炭素数１～１０の炭化水素基、炭素数１～１０のアルコキシ基で置換された炭素数２～２０の炭化水素基、炭素数６～１０のアリールオキシ基で置換された炭素数７～２０の炭化水素基、炭素原子数１～１０のアルコキシ基、または炭素数６～１０のアリールオキシ基を表す。＊は結合手を表す。）

(In the general formula (2), R ^c , R ^d , R ^e , R ^f , R ^g , R ^h , R ⁱ , and R ^j are each independently a hydrogen atom, a halogen atom, or a C 1-10 a hydrocarbon group, a hydrocarbon group having 1 to 10 carbon atoms substituted with a halogen atom, a hydrocarbon group having 2 to 20 carbon atoms substituted with an alkoxy group having 1 to 10 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms; represents a hydrocarbon group having 7 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, and * represents a bond.)

R ^c , R ^d , R ^e , R ^f , R ^g , R ^h , R ⁱ , and R ^j are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or the number of carbon atoms substituted with a halogen atom It may be a hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms.
R ^c , R ^d , R ^e , R ^f , R ^g , R ^h , R ⁱ , and R ^j are each independently preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, A hydrogen atom, a straight-chain alkyl group having 1 to 5 carbon atoms, or a branched non-cyclic alkyl group is more preferable, and a hydrogen atom, a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched non-cyclic alkyl group It is even more preferable to have
In general formula (2), the number of substituents other than hydrogen atoms is preferably 3 or less, preferably 2 or less, from the viewpoint of steric hindrance.
Also, whether all of R ^c , R ^d , R ^e , R ^f , R ^g , R ^h , R ⁱ , and R ^j are hydrogen atoms; R ^c , R ^e , R ^f , R ^g , R ^h , and R ^j are each hydrogen atoms, and R ^d and R ⁱ are each independently a hydrocarbon group having 1 to 10 carbon atoms; and R ^c , R ^d , R ^f , R ^g , R ⁱ , and R ^j is each a hydrogen atom, and R ^e and R ^h are each independently a hydrocarbon group having 1 to 10 carbon atoms; R ^c , R ^d , R ^e , R ^h , R ⁱ and R ^j are each It is preferably a hydrogen atom and R ^f and R ^g are each independently a hydrocarbon group having 1 to 10 carbon atoms from the viewpoint of steric hindrance.

Specific examples of general formula (2) include 9-fluorenyl group, 1-methyl-9-fluorenyl group, 2-methyl-9-fluorenyl group, 3-methyl-9-fluorenyl group, 4-methyl-9-fluorenyl group, 1-ethyl-9-fluorenyl group, 2-ethyl-9-fluorenyl group, 3-ethyl-9-fluorenyl group, 4-ethyl-9-fluorenyl group, 1-n-propyl-9-fluorenyl group, 2 -n-propyl-9-fluorenyl group, 3-n-propyl-9-fluorenyl group, 4-n-propyl-9-fluorenyl group, 1-isopropyl-9-fluorenyl group, 2-isopropyl-9-fluorenyl group, 3-isopropyl-9-fluorenyl group, 4-isopropyl-9-fluorenyl group, 1-n-butyl-9-fluorenyl group, 2-n-butyl-9-fluorenyl group, 3-n-butyl-9-fluorenyl group , 4-n-butyl-9-fluorenyl group, 1-isobutyl-9-fluorenyl group, 2-isobutyl-9-fluorenyl group, 3-isobutyl-9-fluorenyl group, 4-isobutyl-9-fluorenyl group, 1- sec-butyl-9-fluorenyl group, 2-sec-butyl-9-fluorenyl group, 3-sec-butyl-9-fluorenyl group, 4-sec-butyl-9-fluorenyl group, 1-t-butyl-9- fluorenyl group, 2-t-butyl-9-fluorenyl group, 3-t-butyl-9-fluorenyl group, 4-t-butyl-9-fluorenyl group, 1-methoxy-9-fluorenyl group, 2-methoxy-9 -fluorenyl group, 3-methoxy-9-fluorenyl group, 4-methoxy-9-fluorenyl group, 1-ethoxy-9-fluorenyl group, 2-ethoxy-9-fluorenyl group, 3-ethoxy-9-fluorenyl group, 4 -ethoxy-9-fluorenyl group, 1-phenoxy-9-fluorenyl group, 2-phenoxy-9-fluorenyl group, 3-phenoxy-9-fluorenyl group, 4-phenoxy-9-fluorenyl group, 1-trifluoromethyl- 9-fluorenyl group, 2-trifluoromethyl-9-fluorenyl group, 3-trifluoromethyl-9-fluorenyl group, 4-trifluoromethyl-9-fluorenyl group,

1,2-dimethyl-9-fluorenyl group, 1,3-dimethyl-9-fluorenyl group, 1,4-dimethyl-9-fluorenyl group, 1,5-dimethyl-9-fluorenyl group, 1,6-dimethyl- 9-fluorenyl group, 1,7-dimethyl-9-fluorenyl group, 1,8-dimethyl-9-fluorenyl group, 2,3-dimethyl-9-fluorenyl group, 2,4-dimethyl-9-fluorenyl group, 2 ,5-dimethyl-9-fluorenyl group, 2,6-dimethyl-9-fluorenyl group, 2,7-dimethyl-9-fluorenyl group, 3,4-dimethyl-9-fluorenyl group, 3,5-dimethyl-9 -fluorenyl group, 3,6-dimethyl-9-fluorenyl group, 4,5-dimethyl-9-fluorenyl group, 1,2-diethyl-9-fluorenyl group, 1,3-diethyl-9-fluorenyl group, 1, 4-diethyl-9-fluorenyl group, 1,5-diethyl-9-fluorenyl group, 1,6-diethyl-9-fluorenyl group, 1,7-diethyl-9-fluorenyl group, 1,8-diethyl-9- fluorenyl group, 2,3-diethyl-9-fluorenyl group, 2,4-diethyl-9-fluorenyl group, 2,5-diethyl-9-fluorenyl group, 2,6-diethyl-9-fluorenyl group, 2,7 -Diethyl-9-fluorenyl group, 3,4-diethyl-9-fluorenyl group, 3,5-diethyl-9-fluorenyl group, 3,6-diethyl-9-fluorenyl group, 4,5-diethyl-9-fluorenyl group, 1,2-di(n-propyl)-9-fluorenyl group, 1,3-di(n-propyl)-9-fluorenyl group, 1,4-di(n-propyl)-9-fluorenyl group, 1,5-di(n-propyl)-9-fluorenyl group, 1,6-di(n-propyl)-9-fluorenyl group, 1,7-di(n-propyl)-9-fluorenyl group, 1, 8-di(n-propyl)-9-fluorenyl group, 2,3-di(n-propyl)-9-fluorenyl group, 2,4-di(n-propyl)-9-fluorenyl group, 2,5- Di(n-propyl)-9-fluorenyl group, 2,6-di(n-propyl)-9-fluorenyl group, 2,7-di(n-propyl)-9-fluorenyl group, 3,4-di( n-propyl)-9-fluorenyl group, 3,5-di(n-propyl)-9-fluorenyl group, 3,6-di(n-propyl)-9-fluorenyl group, 4,5-di(n- propyl)-9-fluorenyl group, 1,2-diiso Lopyl-9-fluorenyl group, 1,3-diisopropyl-9-fluorenyl group, 1,4-diisopropyl-9-fluorenyl group, 1,5-diisopropyl-9-fluorenyl group, 1,6-diisopropyl-9-fluorenyl group , 1,7-diisopropyl-9-fluorenyl group, 1,8-diisopropyl-9-fluorenyl group, 2,3-diisopropyl-9-fluorenyl group, 2,4-diisopropyl-9-fluorenyl group, 2,5-diisopropyl -9-fluorenyl group, 2,6-diisopropyl-9-fluorenyl group, 2,7-diisopropyl-9-fluorenyl group, 3,4-diisopropyl-9-fluorenyl group, 3,5-diisopropyl-9-fluorenyl group, 3,6-diisopropyl-9-fluorenyl group, 4,5-diisopropyl-9-fluorenyl group,

1,2-di-t-butyl-9-fluorenyl group, 1,3-di-t-butyl-9-fluorenyl group, 1,4-di-t-butyl-9-fluorenyl group, 1,5-di -t-butyl-9-fluorenyl group, 1,6-di-t-butyl-9-fluorenyl group, 1,7-di-t-butyl-9-fluorenyl group, 1,8-di-t-butyl- 9-fluorenyl group, 2,3-di-t-butyl-9-fluorenyl group, 2,4-di-t-butyl-9-fluorenyl group, 2,5-di-t-butyl-9-fluorenyl group, 2,6-di-t-butyl-9-fluorenyl group, 2,7-di-t-butyl-9-fluorenyl group, 3,4-di-t-butyl-9-fluorenyl group, 3,5-di -t-butyl-9-fluorenyl group, 3,6-di-t-butyl-9-fluorenyl group, 4,5-di(t-butyl)-9-fluorenyl group, 1,2-dimethoxy-9-fluorenyl group, 1,3-dimethoxy-9-fluorenyl group, 1,4-dimethoxy-9-fluorenyl group, 1,5-dimethoxy-9-fluorenyl group, 1,6-dimethoxy-9-fluorenyl group, 1,7- Dimethoxy-9-fluorenyl group, 1,8-dimethoxy-9-fluorenyl group, 2,3-dimethoxy-9-fluorenyl group, 2,4-dimethoxy-9-fluorenyl group, 2,5-dimethoxy-9-fluorenyl group , 2,6-dimethoxy-9-fluorenyl group, 2,7-dimethoxy-9-fluorenyl group, 3,4-dimethoxy-9-fluorenyl group, 3,5-dimethoxy-9-fluorenyl group, 3,6-dimethoxy -9-fluorenyl group, 4,5-dimethoxy-9-fluorenyl group and the like.

Among these, preferably 9-fluorenyl group, 2,7-dimethyl-9-fluorenyl group, 2,7-di-t-butyl-9-fluorenyl group, 3,6-dimethyl-9-fluorenyl group, 3 ,6-di-t-butyl-9-fluorenyl group, 4,5-dimethyl-9-fluorenyl group, or 4,5-di-t-butyl-9-fluorenyl group, particularly preferably 9-fluorenyl group , or a 3,6-di-t-butyl-9-fluorenyl group.

（前記一般式（３）において、Ｒ^ｋ、Ｒ^ｌ、Ｒ^ｍ、Ｒ^ｎ、Ｒ^ｏ、Ｒ^ｐ、Ｒ^ｑ、Ｒ^ｒ、Ｒ^ｓ、及びＲ^ｔはそれぞれ独立に、水素原子、ハロゲン原子、炭素数１～１０の炭化水素基、ハロゲン原子で置換された炭素数１～１０の炭化水素基、炭素数１～１０のアルコキシ基で置換された炭素数２～２０の炭化水素基、炭素数６～１０のアリールオキシ基で置換された炭素数７～２０の炭化水素基、炭素原子数１～１０のアルコキシ基、または炭素数６～１０のアリールオキシ基を表す。＊は結合手を表す。）

(In the general formula (3), R ^k , R ^l , R ^m , R ⁿ , ^Ro , R ^p , R ^q , R ^r , R ^s and R ^t are each independently a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a hydrocarbon group having 1 to 10 carbon atoms substituted with a halogen atom, a hydrocarbon group having 2 to 20 carbon atoms and substituted with an alkoxy group having 1 to 10 carbon atoms, a carbon number represents a hydrocarbon group having 7 to 20 carbon atoms substituted with an aryloxy group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, * represents a bond; .)

R ^k , R ^l , R ^m , R ⁿ , R ^o , R ^p , R ^q , R ^r , R ^s and R ^t are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom It may be a hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, substituted with .
R ^k , R ^l , R ^m , R ⁿ , R ^o , R ^p , R ^q , R ^r , R ^s and R ^t are each independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms; is preferably a hydrogen atom or a linear alkyl group having 1 to 5 carbon atoms or a branched acyclic alkyl group, more preferably a hydrogen atom or a linear alkyl group having 1 to 4 carbon atoms or a branched is more preferably a non-cyclic alkyl group.
In general formula (3), the number of substituents other than hydrogen atoms is preferably 3 or less, preferably 2 or less, from the viewpoint of steric hindrance.

Also, whether all of ^Rk , ^Rl , ^Rm , ^Rn , ^Ro , ^Rp , ^Rq , ^Rr , ^Rs , and ^Rt are hydrogen atoms; ^Rk , ^Rl , ^Rm , R ⁿ , R ^q , R ^r , R ^s , R ^t and R ^o are each a hydrogen atom, and R ^p is a hydrocarbon group having 1 to 10 carbon atoms; R ^k , R ^l , R ^m , R ⁿ , R ^q , R ^r , R ^s and R ^t are each a hydrogen atom, and R ^o and R ^p are each independently a hydrocarbon group having 1 to 10 carbon atoms; R ^k , R ^l , R whether ^m , R ^o , R ^p , R ^r , R ^s and R ^t are each a hydrogen atom, and R ⁿ and R ^q are each independently a hydrocarbon group having 1 to 10 carbon atoms; R ^k , R ^l , R ⁿ , R ^o , R ^p , R ^q , R ^s , and R ^t are each hydrogen atoms, and R ^m and R ^r are each independently a hydrocarbon group having 1 to 10 carbon atoms; ^k , R ^m , R ⁿ , R ^o , R ^p , R ^q , R ^r , and R ^t are each hydrogen atoms, and R ^l and R ^s are each independently a hydrocarbon group having 1 to 10 carbon atoms. is preferred from the viewpoint of steric hindrance effects.

Specific examples of general formula (3) include a 9,10-dihydro-9-anthracenyl group, a 1-methyl-9,10-dihydro-9-anthracenyl group, and a 2-methyl-9,10-dihydro-9-anthracenyl group. group, 3-methyl-9,10-dihydro-9-anthracenyl group, 4-methyl-9,10-dihydro-9-anthracenyl group, 1-ethyl-9,10-dihydro-9-anthracenyl group, 2-ethyl -9,10-dihydro-9-anthracenyl group, 3-ethyl-9,10-dihydro-9-anthracenyl group, 4-ethyl-9,10-dihydro-9-anthracenyl group, 1-n-propyl-9, 10-dihydro-9-anthracenyl group, 2-n-propyl-9,10-dihydro-9-anthracenyl group, 3-n-propyl-9,10-dihydro-9-anthracenyl group, 4-n-propyl-9 , 10-dihydro-9-anthracenyl group, 1-isopropyl-9,10-dihydro-9-anthracenyl group, 2-isopropyl-9,10-dihydro-9-anthracenyl group, 3-isopropyl-9,10-dihydro- 9-anthracenyl group, 4-isopropyl-9,10-dihydro-9-anthracenyl group, 1-n-butyl-9,10-dihydro-9-anthracenyl group, 2-n-butyl-9,10-dihydro-9 -anthracenyl group, 3-n-butyl-9,10-dihydro-9-anthracenyl group, 4-n-butyl-9,10-dihydro-9-anthracenyl group, 1-isobutyl-9,10-dihydro-9- anthracenyl group, 2-isobutyl-9,10-dihydro-9-anthracenyl group, 3-isobutyl-9,10-dihydro-9-anthracenyl group, 4-isobutyl-9,10-dihydro-9-anthracenyl group, 1- sec-butyl-9,10-dihydro-9-anthracenyl group, 2-sec-butyl-9,10-dihydro-9-anthracenyl group, 3-sec-butyl-9,10-dihydro-9-anthracenyl group, 4 -sec-butyl-9,10-dihydro-9-anthracenyl group, 1-t-butyl-9,10-dihydro-9-anthracenyl group, 2-t-butyl-9,10-dihydro-9-anthracenyl group, 3-t-butyl-9,10-dihydro-9-anthracenyl group, 4-t-butyl-9,10-dihydro-9-anthracenyl group,

1-methoxy-9,10-dihydro-9-anthracenyl group, 2-methoxy-9,10-dihydro-9-anthracenyl group, 3-methoxy-9,10-dihydro-9-anthracenyl group, 4-methoxy-9 , 10-dihydro-9-anthracenyl group, 1-ethoxy-9,10-dihydro-9-anthracenyl group, 2-ethoxy-9,10-dihydro-9-anthracenyl group, 3-ethoxy-9,10-dihydro- 9-anthracenyl group, 4-ethoxy-9,10-dihydro-9-anthracenyl group, 1-phenoxy-9,10-dihydro-9-anthracenyl group, 2-phenoxy-9,10-dihydro-9-anthracenyl group, 3-phenoxy-9,10-dihydro-9-anthracenyl group, 4-phenoxy-9,10-dihydro-9-anthracenyl group, 1-trifluoromethyl-9,10-dihydro-9-anthracenyl group, 2-tri fluoromethyl-9,10-dihydro-9-anthracenyl group, 3-trifluoromethyl-9,10-dihydro-9-anthracenyl group, 4-trifluoromethyl-9,10-dihydro-9-anthracenyl group,

1,2-dimethyl-9,10-dihydro-9-anthracenyl group, 1,3-dimethyl-9,10-dihydro-9-anthracenyl group, 1,4-dimethyl-9,10-dihydro-9-anthracenyl group , 1,5-dimethyl-9,10-dihydro-9-anthracenyl group, 1,6-dimethyl-9,10-dihydro-9-anthracenyl group, 1,7-dimethyl-9,10-dihydro-9-anthracenyl group, 1,8-dimethyl-9,10-dihydro-9-anthracenyl group, 2,3-dimethyl-9,10-dihydro-9-anthracenyl group, 2,4-dimethyl-9,10-dihydro-9- anthracenyl group, 2,5-dimethyl-9,10-dihydro-9-anthracenyl group, 2,6-dimethyl-9,10-dihydro-9-anthracenyl group, 2,7-dimethyl-9,10-dihydro-9 -anthracenyl group, 3,4-dimethyl-9,10-dihydro-9-anthracenyl group, 3,5-dimethyl-9,10-dihydro-9-anthracenyl group, 3,6-dimethyl-9,10-dihydro- 9-anthracenyl group, 4,5-dimethyl-9,10-dihydro-9-anthracenyl group, 1,2-diethyl-9,10-dihydro-9-anthracenyl group, 1,3-diethyl-9,10-dihydro -9-anthracenyl group, 1,4-diethyl-9,10-dihydro-9-anthracenyl group, 1,5-diethyl-9,10-dihydro-9-anthracenyl group, 1,6-diethyl-9,10- dihydro-9-anthracenyl group, 1,7-diethyl-9,10-dihydro-9-anthracenyl group, 1,8-diethyl-9,10-dihydro-9-anthracenyl group, 2,3-diethyl-9,10 -dihydro-9-anthracenyl group, 2,4-diethyl-9,10-dihydro-9-anthracenyl group, 2,5-diethyl-9,10-dihydro-9-anthracenyl group, 2,6-diethyl-9, 10-dihydro-9-anthracenyl group, 2,7-diethyl-9,10-dihydro-9-anthracenyl group, 3,4-diethyl-9,10-dihydro-9-anthracenyl group, 3,5-diethyl-9 , 10-dihydro-9-anthracenyl group, 3,6-diethyl-9,10-dihydro-9-anthracenyl group, 4,5-diethyl-9,10-dihydro-9-anthracenyl group,

1,2-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 1,3-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 1,4-di( n-propyl)-9,10-dihydro-9-anthracenyl group, 1,5-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 1,6-di(n-propyl)-9 , 10-dihydro-9-anthracenyl group, 1,7-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 1,8-di(n-propyl)-9,10-dihydro-9 -anthracenyl group, 2,3-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 2,4-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 2, 5-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 2,6-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 2,7-di(n- propyl)-9,10-dihydro-9-anthracenyl group, 3,4-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 3,5-di(n-propyl)-9,10 -dihydro-9-anthracenyl group, 3,6-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 4,5-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 1,2-diisopropyl-9,10-dihydro-9-anthracenyl group, 1,3-diisopropyl-9,10-dihydro-9-anthracenyl group, 1,4-diisopropyl-9,10-dihydro-9- anthracenyl group, 1,5-diisopropyl-9,10-dihydro-9-anthracenyl group, 1,6-diisopropyl-9,10-dihydro-9-anthracenyl group, 1,7-diisopropyl-9,10-dihydro-9 -anthracenyl group, 1,8-diisopropyl-9,10-dihydro-9-anthracenyl group, 2,3-diisopropyl-9,10-dihydro-9-anthracenyl group, 2,4-diisopropyl-9,10-dihydro- 9-anthracenyl group, 2,5-diisopropyl-9,10-dihydro-9-anthracenyl group, 2,6-diisopropyl-9,10-dihydro-9-anthracenyl group, 2,7-diisopropyl-9,10-dihydro -9-anthracenyl group, 3,4-diisopropyl-9,10-dihydro-9-anthracenyl group, 3,5-diisopropyl -9,10-dihydro-9-anthracenyl group, 3,6-diisopropyl-9,10-dihydro-9-anthracenyl group, 4,5-diisopropyl-9,10-dihydro-9-anthracenyl group, 1,2- di-t-butyl-9,10-dihydro-9-anthracenyl group, 1,3-di-t-butyl-9,10-dihydro-9-anthracenyl group, 1,4-di-t-butyl-9, 10-dihydro-9-anthracenyl group, 1,5-di-t-butyl-9,10-dihydro-9-anthracenyl group, 1,6-di-t-butyl-9,10-dihydro-9-anthracenyl group , 1,7-di-t-butyl-9,10-dihydro-9-anthracenyl group, 1,8-di-t-butyl-9,10-dihydro-9-anthracenyl group, 2,3-di-t -butyl-9,10-dihydro-9-anthracenyl group, 2,4-di-t-butyl-9,10-dihydro-9-anthracenyl group, 2,5-di-t-butyl-9,10-dihydro -9-anthracenyl group, 2,6-di-t-butyl-9,10-dihydro-9-anthracenyl group, 2,7-di-t-butyl-9,10-dihydro-9-anthracenyl group, 3, 4-di-t-butyl-9,10-dihydro-9-anthracenyl group, 3,5-di-t-butyl-9,10-dihydro-9-anthracenyl group, 3,6-di-t-butyl- 9,10-dihydro-9-anthracenyl group, 4,5-di(t-butyl)-9,10-dihydro-9-anthracenyl group,

1,2-dimethoxy-9,10-dihydro-9-anthracenyl group, 1,3-dimethoxy-9,10-dihydro-9-anthracenyl group, 1,4-dimethoxy-9,10-dihydro-9-anthracenyl group , 1,5-dimethoxy-9,10-dihydro-9-anthracenyl group, 1,6-dimethoxy-9,10-dihydro-9-anthracenyl group, 1,7-dimethoxy-9,10-dihydro-9-anthracenyl group, 1,8-dimethoxy-9,10-dihydro-9-anthracenyl group, 2,3-dimethoxy-9,10-dihydro-9-anthracenyl group, 2,4-dimethoxy-9,10-dihydro-9- anthracenyl group, 2,5-dimethoxy-9,10-dihydro-9-anthracenyl group, 2,6-dimethoxy-9,10-dihydro-9-anthracenyl group, 2,7-dimethoxy-9,10-dihydro-9 -anthracenyl group, 3,4-dimethoxy-9,10-dihydro-9-anthracenyl group, 3,5-dimethoxy-9,10-dihydro-9-anthracenyl group, 3,6-dimethoxy-9,10-dihydro- 9-anthracenyl group, 4,5-dimethoxy-9,10-dihydro-9-anthracenyl group,

10-methyl-9,10-dihydro-9-anthracenyl group, 10-ethyl-9,10-dihydro-9-anthracenyl group, 10-n-propyl-9,10-dihydro-9-anthracenyl group, 10-isopropyl -9,10-dihydro-9-anthracenyl group, 10-n-butyl-9,10-dihydro-9-anthracenyl group, 10-isobutyl-9,10-dihydro-9-anthracenyl group, 10-sec-butyl- 9,10-dihydro-9-anthracenyl group, 10-t-butyl-9,10-dihydro-9-anthracenyl group, 10-methoxy-9,10-dihydro-9-anthracenyl group, 10-ethoxy-9,10 -dihydro-9-anthracenyl group, 10-phenoxy-9,10-dihydro-9-anthracenyl group, 10-trifluoromethyl-9,10-dihydro-9-anthracenyl group, 10-dimethyl-9,10-dihydro- 9-anthracenyl group, 10-diethyl-9,10-dihydro-9-anthracenyl group, 10-di(n-propyl)-9,10-dihydro-9-anthracenyl group, 10-diisopropyl-9,10-dihydro- 9-anthracenyl group, 10-di(n-butyl)-9,10-dihydro-9-anthracenyl group, 10-diisobutyl-9,10-dihydro-9-anthracenyl group, 10-di(sec-butyl)-9 , 10-dihydro-9-anthracenyl group, 10-di(t-butyl)-9,10-dihydro-9-anthracenyl group, 10-dimethoxy-9,10-dihydro-9-anthracenyl group, 10-diethoxy-9 , 10-dihydro-9-anthracenyl group, 10-diphenoxy-9,10-dihydro-9-anthracenyl group, 10-ditrifluoromethyl-9,10-dihydro-9-anthracenyl group and the like.

Among these, preferably 9,10-dihydro-9-anthracenyl group, 2,7-dimethyl-9,10-dihydro-9-anthracenyl group, 2,7-di-t-butyl-9,10-dihydro -9-anthracenyl group, 3,6-dimethyl-9,10-dihydro-9-anthracenyl group, 3,6-di-t-butyl-9,10-dihydro-9-anthracenyl group, 4,5-dimethyl- 9,10-dihydro-9-anthracenyl group, 4,5-di-t-butyl-9,10-dihydro-9-anthracenyl group, 10-methyl-9,10-dihydro-9-anthracenyl group, 10-dimethyl -9,10-dihydro-9-anthracenyl group, particularly preferably 9,10-dihydro-9-anthracenyl group.

E ¹ represents a phosphorus atom, an arsenic atom or an antimony atom. Among these, E1 is preferably ^a phosphorus atom from the viewpoint of coordinating power to the metal.
X1 represents ^an oxygen atom _, a sulfur atom or SO3. Among these, X1 is preferably ^an oxygen atom from the standpoint of acidity for deprotonation.
Z represents a hydrogen atom or a leaving group. Specific examples of Z include a hydrogen atom, a halogen atom, R ⁹ SO ₂ groups (wherein R ⁹ is as described above), CF ₃ SO ₂ groups, and the like. The halogen atom may be a bromine atom or an iodine atom, and specific examples of the R ⁹ SO ₂ group include a tosyl group (p-toluenesulfonyl group) and a mesyl group (methanesulfonyl group).
m represents the valence of Z;

Although general formula [II] is represented in the form of an anion, any counter cation can be used as long as it does not inhibit the reaction with the transition metal compound in the present invention. Specific examples of counter cations include ammonium, quaternary ammonium, phosphonium, and metal ions of groups 1 to 14 of the periodic table. Among these, preferably NH ₄ ⁺ , R ⁹⁴ N ⁺ (here, R ⁹ is as described above, and the _four R ⁹ may be the same or different. The same shall apply hereinafter.), R ⁹⁴ P ⁺ , Li ⁺ , Na ⁺ , K ⁺ , Mg ²⁺ , Ca ²⁺ , Al ³⁺ , more preferably _{R 94} ^{N +} , Li ⁺ , Na ⁺ , K ⁺ .

Tables 1 and 2 below show specific combinations of substituents and the like in the general formulas [I] and [II] in the present invention. Z and m relate only to general formula [I]. However, specific examples are not limited to the following examples.

The compounds represented by general formulas [I] and [II] can be synthesized based on known synthetic methods.

The transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table used in the present invention reacts with the compound represented by the general formula [I] or [II] and has the ability to polymerize. Those capable of forming complexes are used. These are sometimes called precursors.
As a transition metal compound containing a transition metal of Groups 9, 10 or 11, a transition metal compound represented by the following general formula [IV] can be used. can be used.
General formula [IV]: MR ^7′ _p L ¹ _q R ¹³ _r
(Here, M is a group 9, 10 or 11 transition metal atom, R ^7' is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom, or represents a neutral ligand coordinated to M, L ¹ represents a ligand coordinated to M, R ^7′ and L ¹ may combine to form a ring, R ¹³ is a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 30 carbon atoms which may contain a heteroatom, OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁸ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O ) (OR ⁹ ) ₂ M′ or an epoxy-containing group (wherein R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms , M′ represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium, x represents an integer of 0 to 3, y represents an integer of 0 to 2.) p represents 1 , q is an integer of 1 or more, r is an integer of 0 or more, and p+q+r satisfies the valence of M.)

In the present invention, M is a transition metal atom belonging to group 9, 10 or 11 of the periodic table. M is preferably a Group 10 nickel atom, a palladium atom, a platinum atom, a Group 9 cobalt atom, a rhodium atom and a Group 11 copper atom, more preferably a Group 10 nickel atom, a palladium atom or a platinum atom. and most preferably a Group 10 nickel or palladium atom.
The valence of M may be bivalent. Here, the valence of M means the formal oxidation number used in organometallic chemistry. In other words, it refers to the number of charges remaining on an atom of an element when the electron pairs in the bond involved in that element are assigned to an element with high electronegativity. For example, in the general formula [III] described later, E ¹ is a phosphorus atom, X ¹ is an oxygen atom, M is a nickel atom, R ^7' is a phenyl group, L ¹ is pyridine, and the nickel atom is a phosphorus atom and an oxygen atom. , the carbon atom of a phenyl group, or the nitrogen atom of pyridine, the formal oxidation number of the nickel atom, that is, the valence of the nickel atom is bivalent. Because, based on the definitions above, in these bonds electron pairs are assigned to the phosphorous, oxygen, carbon, and nitrogen atoms, which are more electronegative than the nickel atom, and the charges are assigned to the phosphorous atom at 0, This is because the oxygen atom is −1, the phenyl group is −1, the pyridine is 0, and the complex as a whole is electrically neutral, so the charge remaining on the nickel atom is +2.
As the divalent transition metal, for example, nickel (II), palladium (II), platinum (II), and cobalt (II) are preferable. good.

In the present invention, R ^7′ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom, or a neutral ligand coordinated to M.
Specific examples of R ^7′ include hydride group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, n-hexyl group, n-octyl group and n-decyl group. , n-dodecyl group, cyclopentyl group, cyclohexyl group, benzyl group, phenyl group, p-methylphenyl group, trimethylsilyl group, triethylsilyl group, triphenylsilyl group and the like.
Also, when M is a nickel atom and a zero-valent transition metal compound, R ^7′ may be a neutral ligand coordinated to M. The neutral ligand coordinated to M at R ^7′ is a neutral electron-donating ligand. One example is a ligand that is electrically neutral and capable of forming a coordinate bond by coordinating an unpaired electron to the metal M, and has an unpaired electron: a nitrogen atom, a phosphorus atom, an arsenic atom, Hydrocarbon compounds having 1 to 20 carbon atoms having an oxygen atom, a sulfur atom, a selenium atom and the like are included. Another example is a hydrocarbon compound optionally containing a heteroatom having a carbon-carbon unsaturated bond capable of coordinating to a transition metal, specifically a π-donating bond by donating a π-electron. compounds such as ethylene, cyclooctadiene that form a , and compounds such as dibenzylideneacetone (dba) that have unsaturated bonds and heteroatoms coordinating to the metal. Examples of these include those known as neutral ligands of metal complexes such as acetonitrile, isonitrile, carbon monoxide, ethylene and tetrahydrofuran, and ligands that donate π electrons such as allyl and cyclopentadienyl.

The ligand L ¹ in the present invention is a hydrocarbon compound having 1 to 20 carbon atoms and having an unpaired electron, such as a nitrogen atom, a phosphorus atom, an arsenic atom, an oxygen atom, a sulfur atom, or a selenium atom, as an atom capable of coordinative bonding. be. As L ¹ , a hydrocarbon compound optionally containing a heteroatom having a carbon-carbon unsaturated bond capable of coordinating to a transition metal can also be used. Preferably, L ¹ has 1 to 16 carbon atoms, more preferably 1 to 10 carbon atoms. A compound having no electric charge is preferable as L ¹ that coordinates with M in general formula [III] described later.

Preferable L ¹ in the present invention includes cyclic unsaturated hydrocarbons, phosphines, pyridines, piperidines, alkyl ethers, aryl ethers, alkylaryl ethers, cyclic ethers, alkylnitrile derivatives, arylnitrile derivatives, Alcohols, amides, aliphatic esters, aromatic esters, amines and the like can be mentioned. More preferable L ¹ includes cyclic olefins, phosphines, pyridines, cyclic ethers, aliphatic esters, and aromatic esters, and particularly preferable L ¹ is trialkylphosphine, pyridine, lutidine (dimethylpyridine ), picoline (methylpyridine), R ⁹ CO ₂ R ⁹ (R ⁹ is defined as above).
In addition, R ^7′ and L ¹ may combine with each other to form a ring. Examples thereof include 1,5-cyclooctadiene and the π-allyl bonding mode represented by the following general formula [IV-1], which are also preferred embodiments of the present invention.
The π-allyl bonding mode represented by the general formula [IV-1] below indicates only the portion in which M and R ^7′ and L ¹ are united to form a π-allyl bond in general formula [IV].

［式［ＩＶ－１］中、ここでＲ^１３は、前記のとおりである。］

[In the formula [IV-1], R ¹³ is as defined above. ]

In general formula [IV-1], R ¹³ is preferably a hydrogen atom, a methyl group, an ethyl group, a butyl group, a pentyl group, a hexyl group or a phenyl group.

In the general formula [IV], R ¹³ may not be included, and if it is included, it is substituted with the compound represented by the general formula [I] or [II] to form a metal complex that is a reaction product represents what does not remain in halogen atom for R ¹³ , hydrocarbon group having 1 to 30 carbon atoms optionally containing a hetero atom, OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C (O)R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁸ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N(R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , The P(O)(OR ⁹ ) ₂ M' or epoxy-containing groups may be the same as described above.

Of the transition metal compounds used, for example, a transition metal compound containing a nickel atom is bis(1,5-cyclooctadiene)nickel(0), represented by the general formula: Ni(CH ₂ CR ¹³ CH ₂ ) ₂ complex [wherein R ¹³ is as defined above. ], bis(cyclopentadienyl)nickel(II), a complex represented by the general formula: Ni(CH ₂ SiR ¹³ ₃ ) ₂ L ¹ ₂ (wherein R ¹³ and L ¹ are as defined above. ), a complex represented by the general formula: NiR ^7′ ₂ L ¹ ₂ (here, R ^7′ and L ¹ are as described above), and the like.

Preferred among these transition metal compounds are nickel (0) bis(1,5-cyclooctadiene), NiPhCl(PEt ₃ ) ₂ (hereinafter Ph stands for phenyl and Et for ethyl), NiPhCl(PPh ₃ ) _{2 ,} NiPhCl(TMEDA) (hereinafter TMEDA represents tetramethylethylenediamine), NiArBr(TMEDA) (here, Ar=4-fluorophenyl), Ni(acac) ₂ (hereinafter acac represents acetylacetone), general formula: a complex represented by a complex represented by Ni _{(CH2CR13CH2)2} ⁽ _wherein ^R13 is as defined above), general _formula : Ni(CH ₂ SiR ¹³ ₃ ) ₂ Complex represented by L ¹ ₂ (wherein R ¹³ and L ¹ are as described above), general formula: NiR ^7′ ₂ Complex represented by L ¹ ₂ (where R ^7′ and L ¹ are as described above), Pd(dba) ₂ , Pd ₂ (dba) ₃ , Pd ₃ (dba) ₄ (where dba represents dibenzylideneacetone), Pd (OCOCH ₃ ) ₂ , (1,5-cyclooctadiene)Pd(methyl)(chloride).
Particularly preferred are nickel(0)bis(1,5-cyclooctadiene), NiPhCl(PEt ₃ ) ₂ , NiPhCl(PPh ₃ ) _{2 ,} NiPhCl(TMEDA), NiArBr(TMEDA), Ni(acac) ₂ , Ni (CH ₂ CHCH ₂ ) ₂ , Ni(CH ₂ CMeCH ₂ ) ₂ , Ni(CH ₂ SiMe ₃ ) ₂ (Py) ₂ (hereinafter Py represents pyridine), Ni(CH ₂ SiMe ₃ ) ₂ (Lut ) ₂ (hereinafter Lut represents 2,6-lutidine), NiPh ₂ (Py) ₂ , NiPh ₂ (Lut) ₂ , Pd(dba) ₂ , Pd ₂ (dba) ₃ , Pd ₃ (dba) ₄ (where dba represents dibenzylideneacetone), Pd(OCOCH ₃ ) ₂ , (1,5-cyclooctadiene)Pd(methyl)(chloride).

The reaction product of the present invention is obtained by combining the compound represented by the above general formula [I] or [II] and the above transition metal compound (referred to as [IV]), for example [I] + [II]: [ IV]=1:99 to 99:1 (molar ratio) in an organic solvent such as toluene or benzene at 0 to 100° C. under reduced pressure to increased pressure for 1 second to 86400 seconds. . When using a toluene or benzene solution of bis(1,5-cyclooctadiene)nickel(0)(Ni(COD) ₂ ) as the transition metal compound, the color of the solution changes from yellow to, for example, red. , the formation of the reaction product can be confirmed.

After this reaction, a component constituting the transition metal compound, and a part other than the transition metal in the compound, is replaced by the part excluding Z in general formula [I] or the compound of general formula [II] Substitution produces a metal complex, such as a metal complex represented by the following general formula [III], which is a reaction product of the compound represented by the general formula [I] or [II] and the transition metal compound. Although it is preferable that this substitution reaction proceed quantitatively, in some cases it may not proceed completely. After completion of the reaction, in addition to the metal complex which is the reaction product of the compound represented by the general formula [I] or [II] and the transition metal compound, such as the complex represented by the general formula [III], the general formula [ I], [II], and other components derived from the transition metal compound may coexist, but when performing the polymerization reaction or copolymerization reaction of the present invention, these other components may be removed, It does not have to be removed. In general, it is preferable to remove these other components because high activity can be obtained.

In the reaction product of the compound represented by the general formula [I] or [II] and a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table, the following general formula [III ] is considered to contain a metal complex represented by As a reaction product of a compound having a skeleton similar to the compound represented by the general formula [I] or [II] and a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table have reported the structure of a metal complex having a skeleton similar to that of the metal complex represented by the following general formula [III], and it has been reported that the metal complex exhibits catalytic activity (for example, ACS Macro Lett. 2018, 7, 213-217., Non-Patent Document 3, and Non-Patent Document 4, etc.). Therefore, the reaction product of the compound represented by the general formula [I] or [II] and a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table is It is presumed that a metal complex represented by the following general formula [III] is included. As described later, the reaction product of the compound represented by the general formula [I] or [II] and a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table is an excellent Therefore, the structure represented by the following general formula [III], which is presumed from the reaction mechanism, is presumed to be one of the compounds exhibiting catalytic activity.
However, as described above, the structure of the metal complex that is the reaction product is not limited to the structure represented by general formula [III].

In addition, when producing a metal complex represented by the following general formula [III], the compound represented by the general formula [I] or [II] and the group 9, 10 or 11 of the periodic table A coordinating compound (L ¹ ) or a covalent compound for substituting R ⁷ in general formula [III] may coexist when reacting with a transition metal compound containing a transition metal to which it belongs. .
When a nickel atom or a palladium atom is used as M according to the present invention, the coexistence of a Lewis basic coordinating compound in the system may increase the stability of the resulting metal complex. In such a case, a coordinating compound may coexist as long as the coordinating compound does not inhibit the polymerization reaction or copolymerization reaction of the present invention.
The coordinating compound used in the present invention is a hydrocarbon compound having 1 to 20 carbon atoms having an oxygen atom, a nitrogen atom, a phosphorus atom, an arsenic atom, a sulfur atom, or a selenium atom as an atom capable of coordinative bonding, or , a hydrocarbon compound optionally containing a heteroatom having a carbon-carbon unsaturated bond capable of coordinating to a transition metal, and may be synonymous with L ¹ above.

The covalent compound used in the present invention is a compound in which a ligand derived from a transition metal compound can be substituted for R ⁷ in general formula [III], and may be an organometallic compound. ^R7 is ^incorporated into the polymer as an initiation terminal for the polymerization reaction, and can greatly contribute to the initial rate of the polymerization reaction. .
Examples of the covalent compound include an organic lithium compound, which may be R ⁷ Li (wherein R ⁷ is a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom). , an organolithium compound having a hydrocarbon group of 1 to 10 carbon atoms. Examples of organic lithium compounds having a hydrocarbon group having 1 to 10 carbon atoms include methyllithium, n-butyllithium, phenyllithium and the like. Among these, methyllithium and phenyllithium are preferred, and methyllithium is more preferred.

Moreover, the metal complex of the present invention is a metal complex represented by the following general formula [III].

[R ¹ to R ⁷ , E ¹ , X ¹ , M, and L ¹ in general formula [III] are as follows.
R ¹ has a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a side chain having 3 to 30 carbon atoms. may be a cycloalkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms.
R ² , R ³ and R ⁴ each independently represent an atom or group selected from the group consisting of (i) to (iv) below.
(i) a hydrogen atom (ii) a halogen atom (iii) a linear alkyl group having 1 to 30 carbon atoms, optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom, carbon a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, carbon an arylalkyl group having 7 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms (iv) OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O )(OR ⁸ ) ₂ M′, or an epoxy-containing group. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;
Adjacent substituents of R ² , R ³ and R ⁴ are connected to each other and represent an alicyclic ring, an aromatic ring, or a heterocyclic ring containing a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. may be formed. At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.
^R5 or ^R6 each independently represents a condensed polycyclic hydrocarbon group which may have a substituent.
E ¹ represents a phosphorus atom, an arsenic atom or an antimony atom.
X1 represents ^an oxygen atom _, a sulfur atom or SO3.
M represents a transition metal atom belonging to group 9, 10 or 11 of the periodic table.
R ⁷ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom, or a ligand coordinated to M;
L ¹ represents the ligand coordinated to M;
R ⁷ and L ¹ may combine with each other to form a ring. ]

In general formula [III], R ¹ to R ⁶ , E ¹ and X ¹ are as defined above. Thus, between the metal complex in the reaction product and the metal complex represented by the general formula [III], the main skeleton containing the benzene ring and the substituents (R ¹ to R ⁶ , E ¹ , X ¹ ), there is commonality in the complex structure.
Moreover, M and ^L1 in the general formula [III] are as explained in the transition metal compound.

In the present invention, R ⁷ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom, or a ligand coordinated to M.
R ^7′ in the zero-valent transition metal compound with M being Ni may be a neutral ligand coordinated to M, but the compound represented by the general formula [I] or [II] and M being Ni When reacting with a zero-valent transition metal compound, Ni becomes divalent, so ^R7 after the reaction becomes an anionic ligand rather than a neutral ligand. For example, when the compound represented by the general formula [I] or [II] reacts with nickel(0)bis(1,5-cyclooctadiene), the ligand derived from the transition metal compound is R ⁷ and L ¹ combine to form a cycloocten-1-yl group forming a ring.
The polymerization or copolymerization reaction in the present invention is considered to be initiated by inserting an olefin such as propylene or a copolymerization monomer thereof in the present invention into the bond between M and ^R7 . Therefore, if the number of carbon atoms in ^R7 is too large, this initiation reaction tends to be inhibited. Therefore, R ⁷ preferably has 1 to 16 carbon atoms, more preferably 1 to 10 carbon atoms, excluding the carbon atoms contained in the substituent.
Specific examples of R ⁷ include a hydride group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, n-hexyl group, n-octyl group, n-decyl group, n-dodecyl group, cyclopentyl group, cyclohexyl group, benzyl group, phenyl group, p-methylphenyl group, trimethylsilyl group, triethylsilyl group, triphenylsilyl group and the like.
Note that R ⁷ and L ¹ may combine with each other to form a ring. Examples thereof include a cycloocten-1-yl group, an acetylacetonate group and the like, which are also preferred embodiments of the present invention.

Table 2 below shows specific combinations of substituents, etc. in the general formula [III] in the present invention. However, specific examples are not limited to the following examples.

なお、表３及び４において、１，４，５－η－ＣＯＥは、（１，４，５－η）－４－シクロオクテン－１－イル基を表す。

In Tables 3 and 4, 1,4,5-η-COE represents a (1,4,5-η)-4-cycloocten-1-yl group.

In addition, the compounds of complex numbers 1 to 41 shown in Table 2, in which the central metal M is replaced with Pd instead of Ni, are also exemplified.

In the present invention, the reaction of the general formula [I ] or a metal complex that is a reaction product of a compound represented by [II] and a transition metal compound may be subjected to polymerization of an olefin such as propylene or copolymerization of an olefin and a (meth)acrylic acid ester, The reaction may be carried out in the presence of these monomers. The reaction may also be carried out in a reactor used for the polymerization of olefins such as propylene and the copolymerization of olefins with (meth)acrylic acid esters. At this time, these monomers may or may not be present. Further, for the compounds represented by the general formulas [I] and [II], each component may be used alone, or a plurality of components may be used in combination. In particular, for the purpose of widening the molecular weight distribution and comonomer content distribution, such a combination of multiple types is useful.

As described above, the compound represented by the general formula [I] or [II] is brought into contact with a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table, and if necessary Furthermore, by reacting using the coordinating compound or the covalent compound, the compound represented by the general formula [I] or [II] and the transition belonging to Group 9, 10 or 11 of the periodic table The metal complex of the present invention, which is a reaction product with a transition metal compound containing a metal, represented by the general formula [III] can be produced.

2. Olefin Polymerization Catalyst Component The olefin polymerization catalyst component of the present invention is characterized by containing the metal complex of the present invention.
In the present invention, the metal complex of the present invention can be used as a catalyst component for olefin polymerization or copolymerization. As described above, the metal complex of the present invention can be produced by reacting the compound represented by general formula [I] or [II] with a transition metal compound. When the metal complex of the present invention is used as a catalyst component, the reaction solution may be used as it is, the isolated one may be used, or the one supported on a carrier may be used. Supporting on the carrier may be carried out in the presence or absence of these monomers in the reactor used for the polymerization of olefins or the copolymerization of olefins and (meth)acrylic acid esters. may be carried out in a separate container.

Any carrier can be used as long as it does not impair the gist of the present invention. In general, inorganic oxides and polymeric supports are suitable for use. Specific examples include SiO ₂ , Al ₂ O ₃ , MgO, ZrO ₂ , TiO ₂ , B ₂ O ₃ , CaO, ZnO, BaO, ThO ₂ and mixtures thereof, and SiO ₂ —Al ₂ O ₃ , SiO ₂ —V ₂ O ₅ , SiO ₂ —TiO ₂ , SiO ₂ —MgO, SiO ₂ —Cr ₂ O ₃ can also be used, inorganic silicates, polyethylene supports, polypropylene supports, Polystyrene carriers, polyacrylic acid carriers, polymethacrylic acid carriers, polyacrylic acid ester carriers, polyester carriers, polyamide carriers, polyimide carriers and the like can be used. There are no particular restrictions on the particle size, particle size distribution, pore volume, specific surface area, etc. of these carriers, and any carrier can be used.

As the inorganic silicate, clay, clay mineral, zeolite, diatomaceous earth, etc. can be used. These may be synthetic products or naturally occurring minerals. Specific examples of clays and clay minerals include allophane groups such as allophane; kaolin groups such as dickite, nacrite, kaolinite and anoxite; halloysite groups such as metahalloysite and halloysite; Stone family, smectites such as montmorillonite, sauconite, beidellite, nontronite, saponite, and hectorite; vermiculite minerals such as vermiculite; Clay, gayrome clay, hisingerite, pyrophyllite, ryokudei stone group and the like.
These may form a mixed layer. Artificial synthetics include synthetic mica, synthetic hectorite, synthetic saponite, synthetic teniolite, and the like. Among these specific examples, preferably kaolin group such as dickite, nacrite, kaolinite and anoxite, hallosite group such as metahalosite and hallosite, serpentine group such as chrysotile, lizardite and antigorite, montmorillonite, Smectites such as sauconite, beidellite, nontronite, saponite and hectorite; vermiculite minerals such as vermiculite; mica minerals such as illite, sericite and glauconite; synthetic mica, synthetic hectorite, synthetic saponite and synthetic teniolite. Particularly preferred are smectites such as montmorillonite, sauconite, beidellite, nontronite, saponite and hectorite, vermiculite minerals such as vermiculite, synthetic mica, synthetic hectorite, synthetic saponite, and synthetic teniolite.

These supports may be used as they are, but may be treated with hydrochloric acid, nitric acid, sulfuric acid, etc. and/or treated with LiCl, NaCl, KCl, CaCl ₂ , MgCl ₂ , Li ₂ SO ₄ , MgSO ₄ , ZnSO ₄ , Ti ( Salt treatment such as SO ₄ ) ₂ , Zr(SO ₄ ) ₂ , Al ₂ (SO ₄ ) ₃ may be performed. In the treatment, the corresponding acid and base may be mixed to form a salt in the reaction system. Further, shape control such as pulverization or granulation or drying treatment may be performed.

3. Olefin Polymerization Catalyst The olefin polymerization catalyst of the present invention is characterized by containing the following components (A) and (B).
Component (A): the metal complex of the present invention Component (B): an organoaluminum compound

Component (A) is the metal complex of the present invention, and may be used as a single type of metal complex, or as a combination of two or more types of metal complexes.

An example of the organoaluminum compound used as component (B) is represented by the following general formula.
Al(R ^p ) _a X _(3-a)
In the general formula, R ^p is a hydrocarbon group having 1 to 20 carbon atoms, X is a hydrogen atom, a halogen atom, an alkoxy group or a siloxy group, and a is a number greater than 0 and 3 or less.
Specific examples of organoaluminum compounds represented by general formulas include trialkylaluminums such as trimethylaluminum, triethylaluminum, tripropylaluminum, triisobutylaluminum and tri-normaloctylaluminum, diethylaluminum monochloride, diethylaluminum monomethoxide, and the like. or an alkoxy-containing alkylaluminum.

Among these, triisobutylaluminum and tri-normaloctylaluminum are preferred. Also, two or more of the above organoaluminum compounds may be used in combination. Moreover, the above aluminum compound may be modified with alcohol, phenol, or the like. Examples of these modifiers include methanol, ethanol, 1-propanol, isopropanol, butanol, phenol, 2,6-dimethylphenol, 2,6-di-t-butylphenol and the like. -dimethylphenol, 2,6-di-t-butylphenol.

In the method for preparing the olefin polymerization catalyst according to the present invention, the method for contacting the component (A) and the component (B) is not particularly limited.
Different components may be used in mixtures within each component. Moreover, this contact may be carried out not only during catalyst preparation but also during prepolymerization with olefins or during polymerization of olefins.
The contacting of component (A) and component (B) is preferably carried out in an inert hydrocarbon solvent such as pentane, hexane, heptane, toluene and xylene in an inert gas such as nitrogen. The contact can be carried out at a temperature between -20°C and the boiling point of the solvent, preferably at a temperature between room temperature and the boiling point of the solvent.

4. Olefin Polymer Production Method One embodiment of the olefin polymer production method of the present invention comprises polymerizing or copolymerizing an olefin in the presence of the olefin polymerization catalyst of the present invention.
The olefin in the present invention is represented by the general formula: _CH2 = ^CHR10 . Here, R ¹⁰ is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and may have branched, cyclic and/or unsaturated bonds. If the number of carbon atoms in R ¹⁰ is more than 20, there is a tendency that sufficient polymerization activity is not exhibited. Therefore, particularly preferred olefins include those in which R ¹⁰ is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.
More preferred olefins include α-olefins such as ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 3-methyl-1-butene and 4-methyl-1-pentene. , vinylcyclohexene, and styrene. In addition, a single olefin may be used, or a plurality of olefins may be used in combination.
In the method for producing an olefin polymer and the method for producing an olefin copolymer of the present invention, the olefin is particularly preferably propylene.

Another embodiment of the method for producing an olefin polymer of the present invention comprises: (a) an olefin and (b) a (meth)acrylic acid ester monomer, a vinyl monomer or an allyl monomer in the presence of the polymerization catalyst. It is polymerized.

The (meth)acrylate monomer in the present invention is represented by the general formula: CH ₂ =C(R ¹¹ )CO ₂ (R ¹² ). Here, R ¹¹ is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms and may have a branch, ring and/or unsaturated bond. R ¹² is a hydrocarbon group having 1 to 30 carbon atoms and may have branched, cyclic and/or unsaturated bonds. Furthermore, any position within R ¹² may contain a heteroatom.
When the number of carbon atoms in R ¹¹ is 11 or more, there is a tendency that sufficient polymerization activity is not exhibited. Therefore, R ¹¹ is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and preferred (meth)acrylates are those in which R ¹¹ is a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms. is mentioned. More preferable (meth)acrylic acid ester monomers include methacrylic acid esters in which R ¹¹ is a methyl group or acrylic acid esters in which R ¹¹ is a hydrogen atom. Similarly, when the number of carbon atoms in ^R12 exceeds 30, the polymerization activity tends to decrease. Therefore, although R ¹² has 1 to 30 carbon atoms, R ¹² preferably has 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms.
The heteroatom which may be contained in R ¹² includes an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a nitrogen atom, a silicon atom, a fluorine atom, a boron atom and the like. Among these heteroatoms, an oxygen atom, a silicon atom and a fluorine atom are preferred, and an oxygen atom is more preferred. It is also preferred that R ¹² does not contain a heteroatom.

More preferred (meth)acrylate monomers include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, and n-butyl (meth)acrylate. , isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, octyl (meth)acrylate, (meth)acrylic acid 2-ethylhexyl, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, phenyl (meth)acrylate, toluyl (meth)acrylate, benzyl (meth)acrylate, (meth)acrylic Acid hydroxyethyl, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, 2-aminoethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, (meth)acrylate-3 -Methoxypropyl, glycidyl (meth)acrylate, ethylene oxide (meth)acrylate, trifluoromethyl (meth)acrylate, -2-trifluoromethylethyl (meth)acrylate, perfluoroethyl (meth)acrylate, (meth)acrylamide, (meth)acryldimethylamide, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate and the like. A single (meth)acrylic acid ester may be used, or a plurality of (meth)acrylic acid esters may be used in combination.

The vinyl monomer in the present invention is a vinyl monomer having a polar group such as a halogen-containing atom, a nitrogen-containing atom, an oxygen-containing atom or a sulfur-containing atom. It is a vinyl monomer containing an ester group, an epoxy group, a nitrile group, or the like. Specifically, 5-hexen-1-ol, 2-methyl-3-buten-1-ol, ethyl 10-undecenoate, 10-undecen-1-ol, 12-tridecen-2-ol, 10-undecanoic acid, methyl-9-decenate, t-butyl-10-undecenate, 1,1-dimethyl-2-propen-1-ol, 9-decen-1-ol, 3-butenoic acid, 3-buten-1-ol , N-(3-buten-1-yl)phthalimide, 5-hexenoic acid, methyl 5-hexenoate, 5-hexene-2-one, acrylonitrile, methacrylonitrile, vinyl acetate and the like. Among these, 3-buten-1-ol, ethyl 10-undecenoate, and 10-undecen-1-ol are particularly preferred.

The allyl monomer in the present invention is exemplified by an allyl monomer having 3 carbon atoms (propenyl monomer) and an allyl group-containing allyl monomer having 4 or more carbon atoms. Allyl monomers are allyl monomers having polar groups such as halogen-containing, nitrogen-containing, oxygen-containing, and sulfur-containing atoms. It is a vinyl monomer containing an epoxy group, a nitrile group, or the like. Preferred specific examples include allyl acetate, allyl alcohol, allylamine, N-allylaniline, Nt-butoxycarbonyl-N-allylamine, N-benzyloxycarbonyl-N-allylamine, N-allyl-N-benzylamine, allyl chloride , allyl bromide, allyl ether, diallyl ether, and the like. Among these, allyl acetate and allyl alcohol are particularly preferred, and allyl acetate, allyl ether and diallyl ether are more preferred.

The polymerization reaction of the present invention includes hydrocarbon solvents such as propane, n-butane, isobutane, n-hexane, n-heptane, toluene, xylene, cyclohexane, and methylcyclohexane, liquids such as liquefied α-olefins, diethyl ether, It is carried out in the presence or absence of polar solvents such as ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, ethyl acetate, methyl benzoate, acetone, methyl ethyl ketone, formamide, acetonitrile, methanol, isopropyl alcohol, ethylene glycol and the like. Mixtures of the liquid compounds described herein may also be used as solvents. Furthermore, ionic liquids can also be used as solvents. In order to obtain high polymerization activity and high molecular weight, the above-described hydrocarbon solvents and ionic liquids are more preferable.

In the present invention, the polymerization reaction can be carried out in the presence or absence of known additives. As the additive, a polymerization inhibitor for inhibiting radical polymerization and an additive for stabilizing the produced copolymer are preferable. Examples of preferred additives include quinone derivatives and hindered phenol derivatives. Specifically, monomethyl ether hydroquinone, 2,6-di-t-butyl 4-methylphenol (BHT), reaction products of trimethylaluminum and BHT, reaction products of tetravalent titanium alkoxide and BHT, etc. is available. In addition, inorganic and/or organic fillers may be used as additives, and the polymerization may be carried out in the presence of these fillers. Furthermore, L1 or ^an ionic liquid according to the present invention may be used as an additive.

Preferred additives in the present invention include Lewis bases. By selecting a suitable Lewis base, the activity, molecular weight and copolymerizability of the acrylate can be improved. The amount of the Lewis base is 0.0001 to 1000 equivalents, preferably 0.1 to 100 equivalents, more preferably 0.3 equivalents, relative to the transition metal M in the catalyst component present in the polymerization system. ~30 equivalents. The method of adding the Lewis base to the polymerization system is not particularly limited, and any method can be used. For example, it may be added by mixing with the catalyst component of the present invention, may be added by mixing with the monomer, or may be added to the polymerization system independently of the catalyst component and the monomer. Moreover, you may use several Lewis bases together. Moreover, the same Lewis base as L ¹ according to the present invention may be used, or a different one may be used.

Lewis bases include aromatic amines, aliphatic amines, alkyl ethers, aryl ethers, alkylaryl ethers, cyclic ethers, alkylnitriles, arylnitriles, alcohols, amides, and aliphatic esters. , aromatic esters, phosphates, phosphites, thiophenes, thianthrenes, thiazoles, oxazoles, morpholines, and cyclic unsaturated hydrocarbons. Among these, particularly preferred Lewis bases are aromatic amines, aliphatic amines, cyclic ethers, aliphatic esters and aromatic esters. Among them, preferred Lewis bases are pyridine derivatives, pyrimidine derivatives, piperidine derivatives, imidazole derivatives, aniline derivatives, piperidine derivatives, triazine derivatives, pyrrole derivatives, furan derivatives.

Specific Lewis base compounds include pyridine, pentafluoropyridine, 2,6-lutidine, 2,4-lutidine, 3,5-lutidine, pyrimidine, N,N-dimethylaminopyridine, N-methylimidazole, 2, 2'-bipyridine, aniline, piperidine, 1,3,5-triazine, 2,4,6-tris(trifluoromethyl)-1,3,5-triazine, 2,4,6-tris(2-pyridyl) -s-triazine, quinoline, 8-methylquinoline, phenazine, 1,10-phenanthroline, N-methylpyrrole, 1,8-diazabicyclo-[5.4.0]-undec-7-ene, 1,4 -diazabicyclo-[2,2,2]-octane, triethylamine, benzonitrile, picoline, triphenylamine, N-methyl-2-pyrrolidone, 4-methylmorpholine, benzoxazole, benzothiazole, furan, 2,5- dimethylfuran, dibenzofuran, xanthene, 1,4-dioxane, 1,3,5-trioxane, dibenzothiophene, thianthrene, triphenylphosphonium cyclopentadienide, triphenylphosphite, triphenylphosphate, tripyrrolidinophosphine, Tris(pyrrolidino)borane and the like can be mentioned.

In the present invention, there are no particular restrictions on the polymerization method. Slurry polymerization in which at least a part of the produced polymer becomes a slurry in the medium, bulk polymerization in which the liquefied monomer itself is used as a medium, gas phase polymerization conducted in the vaporized monomer, or polymer produced in the liquefied monomer at high temperature and high pressure. High-pressure ion polymerization in which at least a part of is dissolved is preferably used. Moreover, any of batch polymerization, semi-batch polymerization, and continuous polymerization may be used. Further, living polymerization may be used, or polymerization may be performed while chain transfer occurs simultaneously. Furthermore, a so-called chain transfer agent (CSA) may be used together to perform chain shuttling or coordinated chain transfer polymerization (CCTP).

Unreacted monomers and medium may be separated from the produced copolymer and recycled for use.
Upon recycling, these monomers and media may be reused after purification, or may be reused without purification. Conventionally known methods can be used to separate the produced copolymer from unreacted monomers and medium. For example, methods such as filtration, centrifugation, solvent extraction, and reprecipitation using a poor solvent can be used.
There are no particular restrictions on the polymerization temperature, polymerization pressure and polymerization time, but usually the optimum settings can be made from the following ranges in consideration of productivity and process capability. That is, the polymerization temperature is usually −20° C. to 290° C., preferably 0° C. to 250° C., the copolymerization pressure is 0.1 MPa to 300 MPa, preferably 0.3 MPa to 250 MPa, and the polymerization time is 0.1 minute. It can be selected from a range of up to 10 hours, preferably 0.5 minutes to 7 hours, more preferably 1 minute to 6 hours.

In the present invention, polymerization is generally carried out under an inert gas atmosphere. For example, a nitrogen, argon, or carbon dioxide atmosphere can be used, with a nitrogen atmosphere being preferred. In addition, a small amount of oxygen or air may be mixed.
There are no particular restrictions on the supply of the catalyst and monomers to the polymerization reactor, and various supply methods can be adopted depending on the purpose. For example, in the case of batch polymerization, it is possible to adopt a method in which a predetermined amount of monomer is supplied to a polymerization reactor in advance, and a catalyst is supplied there. In this case, additional monomer or additional catalyst may be fed to the polymerization reactor. Further, in the case of continuous polymerization, it is possible to employ a method of continuously or intermittently supplying predetermined amounts of monomers and a catalyst to a polymerization reactor to carry out the polymerization reaction continuously.

Regarding the control of the composition of the copolymer, a method of supplying a plurality of monomers to a reactor and changing the supply ratio thereof can generally be used. In addition, there are a method of controlling the copolymerization composition by utilizing the difference in the monomer reactivity ratio due to the difference in the structure of the catalyst, and a method of controlling the copolymerization composition by utilizing the polymerization temperature dependence of the monomer reactivity ratio. .
Conventionally known methods can be used when it is necessary to control the molecular weight of the polymer. That is, a method of controlling the polymerization temperature to control the molecular weight, a method of controlling the monomer concentration to control the molecular weight, a method of using a chain transfer agent to control the molecular weight, and a method of controlling the ligand structure in the transition metal complex to control the molecular weight. and the like. When using a chain transfer agent, a conventionally known chain transfer agent can be used. For example, hydrogen, metal alkyl, and the like can be used.

In particular, the copolymer with a polar group-containing monomer obtained by the present invention has good paintability, printability, antistatic properties, inorganic filler dispersibility, and adhesion with other resins due to the effects based on the polar group of the copolymer. and compatibility with other resins. Utilizing such properties, the copolymer of the present invention can be used for various purposes. For example, it can be used as films, sheets, adhesive resins, binders, compatibilizers, waxes, and the like.

The present invention will be described in more detail in the following Examples and Comparative Examples, but the present invention is not limited by these.
In the following synthesis examples, unless otherwise specified, operations were performed under a purified nitrogen atmosphere, and dehydrated and deoxygenated solvents were used.
Abbreviations used in the description are as follows.
nBu: normal butyl group, iBu: isobutyl group, tBu: tertiary butyl group iPr: isopropyl group, Me: methyl group, Et: ethyl group, Ph: phenyl group OMOM: methoxymethoxy group (-OCH ₂ OCH ₃ )
AcOH: acetic acid, EtOAc: ethyl acetate, THF: tetrahydrofuran, DMF: dimethylformamide dba: dibenzylideneacetone

1. Evaluation method (1) Weight average molecular weight Mw, number average molecular weight Mn and molecular weight distribution Mw/Mn were obtained by the following GPC measurement.
First, about 20 mg of a sample was collected in a vial bottle for PLSP260VS, a high-temperature GPC pretreatment device manufactured by Polymer Laboratories, and o-dichlorobenzene containing BHT as a stabilizer (BHT concentration = 0.5 g/L) was added to obtain a polymer. The concentration was adjusted to 0.1% by mass. The polymer was dissolved by heating to 135° C. in the PL-SP 260VS high-temperature GPC pretreatment device, and filtered through a glass filter to prepare a sample. In addition, in the GPC measurement in the present invention, no polymer was captured by the glass filter. Next, GPC measurement was performed using GPCV 2000 manufactured by Waters Corporation equipped with TSKgel GMH-HT (30 cm×4 columns) manufactured by Tosoh Corporation as columns and an RI detector. As measurement conditions, sample solution injection volume: about 520 μL, column temperature: 135° C., solvent: o-dichlorobenzene, flow rate: 1.0 mL/min were adopted. Calculation of the molecular weight was performed as follows. That is, using a commercially available monodisperse polystyrene as a standard sample, from the polystyrene standard sample and the viscosity formula of the ethylene-based polymer, to create a calibration curve for retention time and molecular weight, molecular weight is calculated based on the calibration curve. gone. As the viscosity formula, [η] = K × Mα is used, and for polystyrene, K = 1.38E-4, α = 0.70, and for propylene-based polymers, K=1.03E-4, α=0.78 were used.

(2) Comonomer content in copolymer: Determined by the following IR analysis.
Using FTIR-8700 manufactured by SHIMADZU, the comonomer content (mol%) was determined by IR measurement of a sample made into a sheet by hot pressing. At that time, in the case of acrylate, the area ratio of 1,740 cm ⁻¹ /730-720 cm ⁻¹ is converted using the following formula.
[Acrylate] = 1.276 (area ratio) - 0.0434

2. Synthesis of Ligand (Synthesis Example 1): Synthesis of Ligand B-482 Ligand B-482 was synthesized according to the following scheme.

(i) Synthesis of Compounds 2 and 4 Synthesized according to JP-A-2019-172983.
(ii) Synthesis of compound 5 To a solution of compound 4 (1.0 g, 3.35 mmol) in THF (20 mL) was added ⁿ BuLi (2.5 M, 1.47 mL) at 0°C, and the mixture was stirred at 25°C for 2 hours. After cooling to −78° C. and stirring for 30 minutes, PCl ₃ (1.38 g, 10.05 mmol) was added to the solution at −78° C. and stirred at 25° C. for 1 hour to give a yellow suspension. The solution was concentrated to give an oily yellow liquid. This mixture was used for the next reaction without purification.

(iii) Synthesis of Compound 7 To a solution of compound 6 (5.0 g, ^30.08 mmol) in THF (80 mL) was added dropwise nBuLi (2.5 M, 13.24 mL) at -78°C, and the temperature was raised to 25°C. and stirred for 2 hours.
A solution of compound 5 (6.01 g, 15.04 mmol) in THF (30 mL) was added dropwise at −78° C. and stirred at 25° C. for 14 hours to obtain a yellow suspension. BH ₃ -Me ₂ S (10 M, 9.02 mL) was added dropwise at 0° C. and stirred at 25° C. for 16 hours to give a yellow suspension. The solution was concentrated to give a yellow solid. The yellow solid was washed with hexane (40 mL) to give compound 7 (7.0 g, 7.91 mmol, 26%) as a white solid.

(iv) Synthesis of ligand B-482 To a solution of compound 7 (2.2 g, 3.27 mmol) in dichloromethane (5 mL) was added HCl/EtOAc (10 M, 100 mL) at 20°C and stirred at 20°C for 2 hours. to give a colorless solution. After the solvent was distilled off under reduced pressure, NaHCO ₃ (100 mL) was added to adjust the pH to 6.5-7.0, extracted with dichloromethane (80 mL×2), and the solvent was distilled off under reduced pressure to obtain a white solid. . Washing with hexane (15 mL x 2) and Et ₂ O (15 mL x 2) gave B-482 (0.85 g, 1.38 mmol, 42%) as a white solid. The measurement results of ¹ HNMR and ³¹ PNMR of the obtained B-482 are shown below.
¹ H NMR (CDCl ₃ , δ, ppm): 7.84 (m, 6H), 7.42 (m, 4H), 7.32 (m, 3H), 7.25 (m, 3H), 7.11 (d, 2H), 6.85 (d, 1H), 6.50 (t, 1H), 6.44 (br, 1H), 5.87 (d, 1H), 5.21 (s, 2H) , 2.14 (m, 2H), 0.979 (d, 6H), 0.896 (d, 6H)
³¹ PNMR (CDCl ₃ , δ, ppm): −24.0 (s).

(Synthesis Example 2): Synthesis of Ligand B-504 Ligand B-504 was synthesized according to the following scheme.

(i) Synthesis of compound 9 A solution of compound 8 (2.0 g, 7.13 mmol), HIO ₄ (650.22 mg, 2.85 mmol) and I ₂ (1.45 g, 5.71 mmol) in AcOH (10 mL) was mixed with H ₂ O (1.28 mL, 71.31 mmol) and H ₂ SO ₄ (499.60 mg, 4.99 mmol) were added and stirred at 20° C. and heated at 75° C. for 20 hours to obtain a black solution. The solution was poured into ice water and extracted with ethyl acetate (150 mL×2). The organic layer was washed with Na ₂ SO ₃ solution, water and brine, dried over Na ₂ SO ₄ , filtered and concentrated to give a bright yellow oil. Isolation by silica gel chromatography gave compound 9 (2.2 g, 4.13 mmol, 58%) as a white solid.

(ii) Synthesis of Compound 10 PPh ₃ (394.24 mg, 1.50 mmol), NiCl ₂ (PPh ₃ ) ₂ (122.91 mg, 187.89 μmol) and Zn (368.58 mg, 5.64 mmol) were added to a reaction vessel. Weighed and added to DMF (20 mL). This solution was stirred at 70° C. for 1 hour, a DMF (20 mL) solution of compound 9 (1.0 g, 1.88 mmol) was slowly added dropwise, and stirred at 70° C. for 24 hours to obtain a black suspension. . Further stirring at 20° C. for 12 hours changed to a gray suspension. HCl (1 M, 30 mL) was added and extracted with ethyl acetate (50 mL x 2). The organic layer was washed with water and _brine , dried over _Na2SO4 , filtered and evaporated. Isolation by silica gel chromatography gave compound 10 (0.05 g, 111.34 μmol) as a pale yellow liquid.

(iii) Synthesis of Compound 11 To a THF (50 mL) solution of Compound 10 (4.0 g, 14.37 mmol) was added nBuLi (2.5 M, 6.32 mL) at -78°C and stirred at 25°C for 2 hours. After cooling to −78° C., a solution of compound 5 (2.87 g, 7.18 mmol) in THF (20 mL) was added dropwise and stirred at 25° C. for 12 hours to obtain a yellow suspension. The solution was concentrated to obtain a yellow oily liquid. It was isolated by silica gel column chromatography and washed with hexane (40 mL×2) to obtain compound 11 (1.7 g, 1.92 mmol, 27%) as a white solid.

(iv) Synthesis of ligand B-504 To a solution of compound 11 (1.6 g, 1.81 mmol) in dichloromethane (1.0 mL) was added HCl/EtOAc (4 M, 130 mL) at 0°C, and the mixture was stirred at 20°C for 2 hours. Stirring gave a pale yellow solution. After evaporating the solvent under reduced pressure, NaHCO ₃ (500 mL) was added to adjust the pH to 6.5 to 7.0, extracted with dichloromethane (150 mL×2), and the organic layer was evaporated under reduced pressure to obtain B-504 ( 1.5 g, 1.79 mmol, 99%) as a pale yellow solid. The measurement results of ¹ HNMR and ³¹ PNMR of the obtained B-502 are shown below.
¹ H NMR (CDCl ₃ , δ, ppm): 7.90 (s, 2H), 7.86 (s, 2H), 7.74 (br, 2H), 7.30 (m, 6H), 7.14 (d, 2H), 6.93 (d, 1H), 6.69 (m, 1H), 6.56 (t, 1H), 6.26 (d, 1H), 5.18 (s, 2H) , 2.40 (m, 2H), 1.47 (s, 18H), 1.43 (s, 18H), 1.06 (d, 6H), 0.865 (d, 6H)
³¹ PNMR (CDCl ₃ , δ, ppm): −29.0 (s).

(Comparative Synthesis Example 1): Synthesis of Ligand B-549 Ligand B-549 was synthesized according to the following scheme.

(i) Synthesis of compound 13 nBuLi (2.5 M, 5.62 mL) was added to a solution of compound 12 (2.25 g, 13.29 mmol) in THF (20 mL) at 0°C and stirred at 20°C for 2.5 hours. . A solution of compound 5 (5.35 g, 13.39 mmol) in THF (20 mL) was added dropwise at −78° C. and stirred at 20° C. for 2 hours to give a yellow solution. This reaction solution was used for the next reaction without purification.

(ii) Synthesis of Compound 14 To a solution of compound 6 (2.23 g, 13.39 mmol) in THF (30 mL) was added nBuLi (2.5 M, 5.89 mL) at -78°C, and the mixture was stirred at 20°C for 2 hours. A solution of compound 13 (7.11 g, 13.39 mmol) in THF (40 mL) was added and stirred at 20° C. for 12 hours to give a yellow suspension. The solution was concentrated to give a gummy yellow solid. Isolation by silica gel chromatography gave Compound 14 (4.85 g, 7.34 mmol, 55%) as a white solid. The measurement results of ¹ HNMR and ³¹ PNMR of compound 14 are shown below.

(iii) Synthesis of B-549 To a solution of compound 14 (4.65 g, 7.04 mmol) in dichloromethane (10 mL) was added HCl/EtOAc (4 M, 80 mL) at 0° C. and stirred at 20° C. for 2 hours to give a colorless solution. got After the solvent was distilled off under reduced pressure, NaHCO ₃ (300 mL) was added to adjust the pH to 6.5-7.0, extracted with dichloromethane (100 mL), and the organic layer was distilled off under reduced pressure to obtain a white solid. Washing with dichloromethane/hexane (1:20, 10 mL) gave B-549 (3.0 g). ¹ HNMR measurement results of the obtained B-549 are shown below.
¹ H NMR (CDCl ₃ , δ, ppm): 8.12 (m, 1H), 7.82 (m, 2H), 7.34 (m, 3H), 7.21 (m, 4H), 7.06 (m, 3H), 6.75 (d, 1H), 6.73 (d, 1H), 6.20 (d, 2H), 6.02 (s, 1H), 3.88 (s, 3H) , 3.81 (s, 6H), 2.73 (m, 1H), 2.55 (m, 1H), 1.17 (d, 3H), 1.08 (d, 3H), 1.06 ( d, 3H), 1.00 (d, 3H)
³¹ PNMR (CDCl ₃ , δ, ppm): −49.8 (s).

(Synthesis Example 3): Synthesis of ligand X-146 Ligand X-146 was synthesized according to the following scheme.

(i) Synthesis of Compounds 2 and 4 Synthesized according to JP-A-2019-172983.
(ii) Synthesis of compound 5 To a solution of compound 4 (1.0 g, 3.35 mmol) in THF (20 mL) was added ⁿ BuLi (2.5 M, 1.47 mL) at 0°C, and the mixture was stirred at 25°C for 2 hours. After cooling to −78° C. and stirring for 30 minutes, PCl ₃ (1.38 g, 10.05 mmol) was added to the solution at −78° C. and stirred at 25° C. for 1 hour to give a yellow suspension. The solution was concentrated to give an oily yellow liquid. This mixture was used for the next reaction without purification.

(iii) Synthesis of Compound 16 To a solution of compound 15 (6.0 g, 33.29 mmol) in THF (100 mL) was added dropwise ⁿ BuLi (2.5 M, 14.65 mL) at -78°C, and the temperature was maintained at -78°C for 2 hours. Stirred.
A solution of compound 5 (6.65 g, 16.64 mmol) in THF (50 mL) was added dropwise at −78° C. and stirred at 20° C. for 16 hours to give a yellow suspension. The reaction was slowly quenched with water (250 mL), extracted with ethyl acetate (250 mL x ₃ ), dried over _Na2SO4 , filtered and the solvent was evaporated. Compound 16 was obtained as a white solid by silica gel chromatography.

(iv) Synthesis of ligand X-146 To a solution of compound 16 (700 mg, 1.02 mmol) in dichloromethane (10 mL) was added HCl/EtOAc (4 M, 10.19 mL) at 0°C, and the mixture was stirred at 20°C for 16 hours. to give a colorless solution. After the solvent was distilled off under reduced pressure, NaHCO ₃ (100 mL) was added to adjust the pH to 6.5-7.0, extracted with dichloromethane (80 mL×2), and the solvent was distilled off under reduced pressure to obtain a white solid. . Washing with hexane (15 mL x 2) and Et ₂ O (15 mL x 2) gave X-146 as a white solid.
The measurement results of ¹ HNMR and ³¹ PNMR of the obtained X-146 are shown below.
¹ H NMR (CDCl ₃ , δ, ppm): 0.930 (br, 12H), 2.09 (br, 2H), 3.51 (m, 2H), 3.67 (m, 2H), 4.85 (br, 1H), 6.62 (m, 1H), 6.60-7.09 (m, 22H).
³¹ PNMR (CDCl ₃ , δ, ppm): −27.1 (s).

3. Polymerization Evaluation (Example 1): Homopolymerization of Propylene Using Ligand B-482 (i) Synthesis of Metal Complex All of the following operations were performed under a nitrogen atmosphere. Bis-1,5-cyclooctadiene nickel(0) is hereinafter referred to as Ni(COD) ₂ .
Ni(COD) ₂ (70.8 mg, 0.257 mmol) was weighed into a two-neck eggplant flask, and toluene (12.85 mL) was added to make a 0.02 mmol/mL solution. 6.95 mL of this toluene solution of Ni(COD) ₂ was added to a two-necked eggplant flask containing B-482 (85.8 mg, 0.139 mmol) obtained in Synthesis Example 1, and stirred at room temperature for 30 minutes.
The color of the reaction solution changed from yellow to orange. A 0.02 mmol/mL solution of the reaction product of B-482 and Ni(COD) ₂ ((B-482)Ni((1,4,5-η)-COE)) was obtained. Here, the concentration of the reaction product was calculated assuming that B-482 and Ni(COD) ₂ reacted in a 1:1 ratio to form a nickel complex.

(ii) Homopolymerization of Propylene Tri-n-octylaluminum (0.1 mmol) was introduced into an induction stirring autoclave having an internal volume of 2 L. After propylene (500 mL) was supplied to the autoclave, a 0.02 mmol/mL solution (5.0 mL) of the reaction product of B-482 and Ni(COD) ₂ obtained in (i) above was supplied and stirred. The autoclave was heated to 50° C. to initiate polymerization. After polymerizing for 1 hour, the reaction was terminated by removing residual propylene. After that, the autoclave was opened to obtain a polymer. Polymerization results are listed in Table 5. The activity represents the polymer yield (g) per 1 mol of the complex used for polymerization. The GPC results for the resulting polymer are also listed in Table 5. The activity was calculated assuming that the ligand B-482 and Ni(COD) ₂ reacted in a 1:1 ratio to form a nickel complex.

(Example 2): Propylene homopolymerization using ligand B-504 (i) Synthesis of metal complex B-504 (87.4 mg, 0.104 mmol) obtained in Synthesis Example 2 was used as a ligand A complex was synthesized in the same manner as in Example 1(i), except that 5.2 mL of a toluene solution of Ni(COD) ₂ (0.02 mmol/mL) was used, and B-504 and Ni(COD) A 0.02 mmol/mL solution of the reaction product of ₂ ((B-504)Ni((1,4,5-η)-COE)) was obtained. Here, the concentration of the reaction product was calculated assuming that B-504 and Ni(COD) ₂ reacted in a 1:1 ratio to form a nickel complex.

(ii) Homopolymerization of propylene Instead of the 0.02 mmol/mL solution of the reaction product of B-482 and Ni(COD) ₂ , the reaction product of B-504 obtained in (i) above and Ni(COD) ₂ Polymerization was carried out in the same manner as in Example 1 (ii), except that 5.2 mL of a 0.02 mmol/mL solution ((B-504) Ni ((1,4,5-η)-COE)) was used. . Table 5 shows the results. The activity was calculated assuming that the ligand B-504 and Ni(COD) ₂ reacted 1:1 to form a nickel complex.

(Example 3): Copolymerization of propylene and ethyl 10-undecenoate using ligand B-482 (i) Synthesis of metal complex B-482 obtained in Synthesis Example 1 as a ligand (80.2 mg , 0.130 mmol) and 6.5 mL of a toluene solution of Ni(COD) ₂ (0.02 mmol/mL). A 0.02 mmol/mL solution of the reaction product of 482 and Ni(COD) ₂ ((B-482)Ni((1,4,5-η)-COE)) was obtained. Here, the concentration of the reaction product was calculated assuming that B-482 and Ni(COD) ₂ reacted in a 1:1 ratio to form a nickel complex.

(ii) Copolymerization of propylene and ethyl 10-undecenoate Reaction product of B-482 obtained in (i) above and Ni(COD) ₂ ((B-482)Ni((1,4,5-η) Polymerization was carried out in the same manner as in Example 1(ii), except that 5.0 mL of the )-COE)) 0.02 mmol/mL solution and ethyl 10-undecenoate (12 mL, 50 mmol) were used. Table 5 shows the results. The activity was calculated assuming that the ligand B-482 and Ni(COD) ₂ reacted in a 1:1 ratio to form a nickel complex.

(Comparative Example 1): Propylene homopolymerization using ligand B-549 (i) Synthesis of comparative metal complex B-549 (51.6 mg, 0.187 mmol) obtained in Comparative Synthesis Example 1 as a ligand ) was used, and a complex was synthesized in the same manner as in Example 1, except that 9.35 mL of a toluene solution of Ni(COD) ₂ (0.02 mmol/mL) was used, and B-549 and Ni(COD) A 0.02 mmol/mL solution of the reaction product of ₂ ((B-549)Ni((1,4,5-η)-COE)) was obtained. Here, the concentration of the reaction product was calculated assuming that B-549 and Ni(COD) ₂ reacted at a ratio of 1:1 to form a nickel complex.

( _ii ) propylene homopolymerization reaction product ((B-549)Ni((1,4,5-η)-COE))( Polymerization was carried out in the same manner as in Example 1(ii), except that 5.0 mL of the 0.02 mmol/mL) solution was used. Table 5 shows the results. The activity was calculated assuming that the ligand B-549 and Ni(COD) ₂ reacted in a 1:1 ratio to form a nickel complex.

(Example 4): Propylene homopolymerization using (B-482) NiMePy (i) Synthesis of metal complex (B-482) NiMePy was synthesized according to the following scheme.

All work was performed under a nitrogen atmosphere. Also, dehydrated solvents were used. Nickel chloride hexahydrate (0.51 g, 2.1 mmol) was placed in a 100 mL two-necked eggplant flask, pyridine (2.0 mL, 25.8 mmol) was added at room temperature, and the mixture was stirred at 40° C. for 30 minutes. The reaction changed momentarily from green to turquoise. After that, the volatile components of the reactant were distilled off under reduced pressure to obtain NiCl ₂ Py ₄ . A toluene/THF solution (9/1 vol%, 20 mL) and pyridine (1.0 mL, 12.9 mmol) were added thereto and stirred at 0°C for 15 minutes to prepare a slurry solution. A diethyl ether solution of methyllithium (1.09 mol/L, 3.9 mL, 4.3 mmol) was slowly added thereto. The solution changed from tan to reddish brown. After that, a toluene solution (20 mL) of B-482 (902.9 mg, 1.47 mmol) was quickly added dropwise at 0° C. via a cannula, and the mixture was heated to 40° C. and stirred for 1 hour. The reaction solution remained reddish brown, and the hue became slightly lighter. After that, the reaction solution was filtered through celite, and the filtrate was concentrated. Hexane (10 mL) was added thereto, the mixture was cooled to 0° C., and the precipitated solid content was collected. After that, the obtained solid content was redissolved in toluene (30 mL), the insoluble matter was filtered, and the filtrate was concentrated to obtain (B-482) NiMePy (0.518 g, yield 45%).
The measurement results of ¹ HNMR and ³¹ PNMR of the obtained (B-482) NiMePy are shown below.
¹ H NMR (C ₆ D ₆ , 23° C., δ): −1.23 (d, J=5.40 Hz, 3H), 0.93 (br, 6H), 1.12 (br, 6H), 2. 38-2.85 (br, 2H), 5.20 (s, 1H), 5.23 (s, 1H), 6.07 (t, J = 7.83Hz, 1H), 6.18 (t, J = 7.02Hz, 1H), 6.47-6.63 (br, 1H), 6.86 (d, J = 7.55Hz, 1H), 7.11-7.35 (m, 19H), 7.65-7.74 (br, 4H).
³¹ P NMR (C ₆ D ₆ , 23° C., δ): 42.6 (s, 1P).

Toluene (8 mL) was added to the two-necked eggplant flask containing the obtained (B-482) NiMePy (76.5 mg, 0.100 mmol) and stirred at room temperature for 30 minutes. .0125 mmol/mL was prepared.

(ii) Propylene Homopolymerization Instead of the 0.02 mmol/mL solution of the reaction product of B-482 and Ni(COD) ₂ , the toluene solution of (B-482) NiMePy obtained in (i) above was added to 8. Polymerization was carried out in the same manner as in Example 1(ii), except that 0 mL was used. Table 6 shows the results.

(Example 5): Propylene homopolymerization using (X-146)NiMePy (i) Synthesis of metal complex (X-146)NiMePy was synthesized according to the following scheme.

All work was performed under a nitrogen atmosphere. Also, dehydrated solvents were used. Nickel chloride hexahydrate (0.51 g, 2.1 mmol) was placed in a 100 mL two-necked eggplant flask, pyridine (2.0 mL, 25.8 mmol) was added at room temperature, and the mixture was stirred at 40° C. for 30 minutes. The reaction changed momentarily from green to turquoise. After that, the volatile components of the reactant were distilled off under reduced pressure to obtain NiCl ₂ Py ₄ . A toluene/THF solution (9/1 vol%, 20 mL) and pyridine (1.0 mL, 12.9 mmol) were added thereto and stirred at 0°C for 15 minutes to prepare a slurry solution. A diethyl ether solution of methyllithium (1.09 mol/L, 3.9 mL, 4.3 mmol) was slowly added thereto. The solution changed from tan to reddish brown. Thereafter, a toluene solution (20 mL) of X-146 (944.1 mg, 1.47 mmol) was quickly added dropwise at 0° C. via a cannula, and the mixture was heated to 40° C. and stirred for 1 hour. The reaction solution remained reddish brown, and the hue became slightly lighter. After that, the reaction solution was filtered through celite, and the filtrate was concentrated. Hexane (10 mL) was added thereto, the mixture was cooled to 0° C., and the precipitated solid content was collected. After that, the obtained solid content was redissolved in toluene (30 mL), the insoluble matter was filtered, and the filtrate was concentrated to obtain (X-146)NiMePy (0.435 g, yield 35%).
The measurement results of ¹ HNMR and ³¹ PNMR of the obtained (X-146)NiMePy are shown below.
¹ H NMR (C ₆ D ₆ , 23° C., δ): −1.11 (d, J=4.30 Hz, 3 H), 0.99 (d, J=7.00 Hz, 6 H), 1.20 (d , J = 7.00 Hz, 6H), 2.51-2.61 (m, 2H), 3.67 (s, 1H), 3.72 (s, 1H), 5.03 (d, J = 6 .86Hz, 1H), 5.07 (d, J = 6.86Hz, 1H), 5.18 (s, 1H), 5.21 (s, 1H), 6.04 (t, J = 7.44Hz , 1H), 6.19 (t, J = 7.35Hz, 1H), 6.86 (d, J = 6.69Hz, 1H), 7.04-7.35 (m, 22H), 7.64 (br, 2H).
³¹ P NMR (C ₆ D ₆ , 23° C., δ): 43.6 (s, 1P).

A complex solution was prepared in the same manner as in Example 4(i), except that the obtained (X-146)NiMePy (83.7 mg, 0.100 mmol) was used.

(ii) Homopolymerization of Propylene Instead of the 0.02 mmol/mL solution of the reaction product of B-482 and Ni(COD) ₂ , the toluene solution of (X-146) NiMePy obtained in (i) above was added to 8. Polymerization was carried out in the same manner as in Example 1(ii), except that 0 mL was used. Table 6 shows the results.

4. Discussion As can be seen from Comparative Example 1 in Table 5 above, in the polypropylene polymerization using the conventional complex (Comparative Example 1), the molecular weight Mw of the obtained polymer is as small as 2,000. On the other hand, as can be seen from Examples 1 and 2 in Table 5 above, in the polypropylene polymerization using the metal complexes of the present invention (Examples 1 and 2), the polymerization activity was 1.4×10 ⁵ (g/mol/hr) or more, and the obtained polymer has a large molecular weight Mw of 10,000 or more.
Furthermore, as can be seen from Example 3, when the metal complex of the present invention is used, even in copolymerization using ethyl 10-undecenoate as a comonomer as a (meth)acrylic acid ester monomer, 7.1 × 10 ⁵ The activity is also high, and the molecular weight Mw of the obtained copolymer is 10,000 or more, which is as large as homopolymerization of propylene.
Further, from Table 6 above, even in Examples 4 and 5 using the metal complexes of the present invention in which the type of transition metal compound was changed, the molecular weight Mw of the resulting polymer was as large as 10,000 or more.
Thus, having two condensed polycyclic hydrocarbon groups on E ¹ capable of reacting with a transition metal and having a specific substituent at the ortho position (R ¹ ) of X ¹ capable of reacting with a transition metal The metal complex of the present invention using the ligand has a significantly higher molecular weight than the ligand having only one condensed polycyclic hydrocarbon group on E1 (Comparative Example ¹ ). It was shown that polypropylene was obtained.
From the above, it is clear that the metal complex of the present invention provides an olefin homopolymer having a higher molecular weight than conventionally with higher activity, and has excellent technical significance.

Claims (27)

A metal complex which is a reaction product of a compound represented by the following general formula [I] or [II] and a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table.

[R ¹ to R ⁶ , E ¹ and X ¹ in formulas [I] and [II] are as follows.
R ¹ has a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a side chain having 3 to 30 carbon atoms. may be a cycloalkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms.
R ² , R ³ and R ⁴ each independently represent an atom or group selected from the group consisting of (i) to (iv) below.
(i) a hydrogen atom (ii) a halogen atom (iii) a linear alkyl group having 1 to 30 carbon atoms, optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom, carbon a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, carbon an arylalkyl group having 7 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms (iv) OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O )(OR ⁸ ) ₂ M′, or an epoxy-containing group. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;
Adjacent substituents of R ² , R ³ and R ⁴ are connected to each other and represent an alicyclic ring, an aromatic ring, or a heterocyclic ring containing a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. may be formed. At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.
^R5 or ^R6 each independently represents a condensed polycyclic hydrocarbon group which may have a substituent.
E ¹ represents a phosphorus atom, an arsenic atom or an antimony atom.
X1 represents ^an oxygen atom _, a sulfur atom or SO3.
Further, in general formula [I],
Z represents a hydrogen atom or a leaving group,
m represents the valence of Z; ] 2. The metal complex according to claim 1, wherein the transition metal compound comprises a transition metal belonging to group 10 of the periodic table. A metal complex represented by the following general formula [III].

[In the general formula [III],
R ¹ has a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a side chain having 3 to 30 carbon atoms. may be a cycloalkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms.
R ² , R ³ and R ⁴ each independently represent an atom or group selected from the group consisting of (i) to (iv) below.
(i) a hydrogen atom (ii) a halogen atom (iii) a linear alkyl group having 1 to 30 carbon atoms, optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom, carbon a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, carbon an arylalkyl group having 7 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms (iv) OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O )(OR ⁸ ) ₂ M′, or an epoxy-containing group. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;
Adjacent substituents of R ² , R ³ and R ⁴ are connected to each other and represent an alicyclic ring, an aromatic ring, or a heterocyclic ring containing a heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. may be formed. At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.
^R5 or ^R6 each independently represents a condensed polycyclic hydrocarbon group which may have a substituent.
E ¹ represents a phosphorus atom, an arsenic atom or an antimony atom.
X1 represents ^an oxygen atom _, a sulfur atom or SO3.
M represents a transition metal atom belonging to group 9, 10 or 11 of the periodic table.
R ⁷ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may contain a heteroatom, or a ligand coordinated to M;
L ¹ represents the ligand coordinated to M;
R ⁷ and L ¹ may combine with each other to form a ring. ] 4. The metal complex according to claim 3, wherein said M comprises a transition metal belonging to group 10 of the periodic table. 5. Any one of claims 1 to 4, wherein R ⁵ or R ⁶ is each independently a condensed polycyclic hydrocarbon group formed by condensing three or more optionally substituted rings. The metal complex described in . 6. The metal according to any one of claims 1 to 5, wherein R ⁵ or R ⁶ is each independently a fluorenyl group or a 9,10-dihydroanthracenyl group, which may have a substituent. Complex. 7. The metal complex according to any one of claims 1 to 6, wherein R ¹ is an aryl group having 6 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms. 8. The metal complex according to any one of claims 1 to 7, wherein R ¹ is a substituent represented by the following general formula (1).

(In the general formula (1), each R ^a independently represents a linear or branched non-cyclic alkyl group having 2 or more carbon atoms, and each R ^b independently represents a hydrogen atom, or a linear or represents a branched acyclic alkyl group, and * represents a bond.) A metal complex according to any one of claims 1 to 8, wherein R ¹ is a 2,6-diisopropylphenyl group. The metal complex according to any one of claims 1 to 9, wherein the transition metal compound contains nickel atoms or palladium atoms. A metal complex according to any one of claims 1 to 10, wherein E ¹ is a phosphorus atom. The metal complex according to any one of claims 1 to 11, wherein X ¹ is an oxygen atom. A catalyst component for olefin polymerization, comprising the metal complex according to any one of claims 1 to 12. An olefin polymerization catalyst comprising a reaction product of a compound represented by the following general formula [I] or [II] and a transition metal compound containing a transition metal belonging to Group 9, 10 or 11 of the periodic table.

[R ¹ to R ⁶ , E ¹ and X ¹ in formulas [I] and [II] are as follows.
R ¹ has a linear alkyl group having 1 to 30 carbon atoms, a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a side chain having 3 to 30 carbon atoms. may be a cycloalkyl group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkylaryl group having 7 to 30 carbon atoms.
R ² , R ³ and R ⁴ each independently represent an atom or group selected from the group consisting of (i) to (iv) below.
(i) a hydrogen atom (ii) a halogen atom (iii) a linear alkyl group having 1 to 30 carbon atoms, optionally having a group selected from the group consisting of a heteroatom and a group containing a heteroatom, carbon a branched acyclic alkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and optionally having a side chain, an aryl group having 6 to 30 carbon atoms, carbon arylalkyl group having 7 to 30 carbon atoms or alkylaryl group having 7 to 30 carbon atoms (iv) OR ⁹ , CO ₂ R ⁹ , CO ₂ M′, C(O)N(R ⁸ ) ₂ , C(O) R ⁹ , OC(O)R ⁹ , SR ⁹ , SO ₂ R ⁹ , SOR ⁹ , OSO ₂ R ⁹ , P(O)(OR ⁹ ) _2-y (R ⁸ ) _y , CN, NHR ⁹ , N( R ⁹ ) ₂ , Si(OR ⁸ ) _3-x (R ⁸ ) _x , OSi(OR ⁸ ) _3-x (R ⁸ ) _x , NO ₂ , SO ₃ M′, PO ₃ M′ ₂ , P(O )(OR ⁸ ) ₂ M′, or an epoxy-containing group. Here, R ⁸ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. Also, R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms. M' represents an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or phosphonium; x is an integer from 0 to 3; y is an integer from 0 to 2;
Adjacent substituents from R ² , R ³ and R ⁴ are connected to each other and an alicyclic ring, an aromatic ring, or a hetero ring containing a hetero atom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom may be formed. At this time, the number of ring members is 5 to 8, and the ring may or may not have a substituent.
^R5 or ^R6 each independently represents a condensed polycyclic hydrocarbon group which may have a substituent.
E ¹ represents a phosphorus atom, an arsenic atom or an antimony atom.
X1 represents ^an oxygen atom _, a sulfur atom or SO3.
Further, in general formula [I],
Z represents a hydrogen atom or a leaving group,
m represents the valence of Z; ] 15. The catalyst for olefin polymerization according to claim 14, wherein the transition metal compound comprises a transition metal belonging to group 10 of the periodic table. 16. The olefin polymerization according to claim ¹⁴ or ¹⁵ , wherein R5 or R6 is each independently a condensed polycyclic hydrocarbon group formed by condensing three or more optionally substituted rings. catalyst for 17. The olefin according to any one of claims 14 to 16, wherein R ⁵ or R ⁶ is each independently a fluorenyl group or a 9,10-dihydroanthracenyl group, which may have a substituent. Polymerization catalyst. The catalyst for olefin polymerization according to any one of claims 14 to 17, wherein R ¹ is an aryl group having 6 to 30 carbon atoms or an alkylaryl group having 7 to 30 carbon atoms. The olefin polymerization catalyst according to any one of claims 14 to 18, wherein R ¹ is a substituent represented by the following general formula (1).

(In the general formula (1), each R ^a independently represents a linear or branched non-cyclic alkyl group having 2 or more carbon atoms, and each R ^b independently represents a hydrogen atom, or a linear or represents a branched acyclic alkyl group, and * represents a bond.) The catalyst for olefin polymerization according to any one of claims 14 to 19, wherein R ¹ is a 2,6-diisopropylphenyl group. The olefin polymerization catalyst according to any one of claims 14 to 20, wherein said transition metal compound contains a nickel atom or a palladium atom. The catalyst for olefin polymerization according to any one of claims 14-21, wherein E ¹ is a phosphorus atom. The olefin polymerization catalyst according to any one of claims 14 to 22, wherein X ¹ is an oxygen atom. An olefin polymerization catalyst comprising the olefin polymerization catalyst component according to claim 13 . The olefin polymerization catalyst according to any one of claims 14 to 24, further comprising the following component (B).
Component (B): an organoaluminum compound. A method for producing an olefin polymer, comprising polymerizing or copolymerizing an olefin in the presence of the olefin polymerization catalyst according to any one of claims 14 to 25. 27. The method for producing an olefin polymer according to claim 26, wherein said olefin is propylene.