Transition metal compound and catalyst composition comprising the same

Abstract

The present invention relates to a transition metal compound having a novel structure and a catalyst composition comprising the same.

Description

[0001] Cross-reference to related applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0021372, filed with the Korean Intellectual Property Office on February 17, 2023, the content of which is incorporated herein by reference. Technical Field

[0003] The present invention relates to a transition metal compound having a novel structure and a catalyst composition including the transition metal compound. Background Art

[0004] Generally, olefin polymers such as ethylene copolymers are polymer materials that can be used as materials for hollow molded products, extrusion molded products, films, sheets, etc., and have been prepared in the presence of a Ziegler-Natta catalyst system.

[0005] The Ziegler-Natta catalyst is a heterogeneous catalyst and is a catalyst in a system where the phase of the reactants is different from the phase of the catalyst, for example, a system of liquid reactants - solid catalyst, etc. Such a Ziegler-Natta catalyst consists of two components and is generally composed of a halogen compound of a transition metal including titanium (Ti), vanadium (V), chromium (Cr), molybdenum (Mo), and zirconium (Zr) (e.g., TiCl4) and alkyllithium, alkylaluminum, etc.

[0006] However, the concentration of the active substance of the Ziegler-Natta catalyst is several to dozens of percentages relative to the transition metal atoms, and most of the transition metal atoms may not exhibit their functions, and there is a defect in that the limitations of being a heterogeneous catalyst cannot be overcome.

[0007] Recently, as a next-generation catalyst that can overcome the above defects, metallocene compounds have received attention. Metallocene compounds are homogeneous catalysts containing metals in Group 4 and are known to exhibit desired polymerization activity in olefin polymerization.

[0008] Most metallocene catalysts for polymerization contain metal elements in Group 4 such as titanium, zirconium, and hafnium (Hf) and supporting ligands as precursors, and consist of two aromatic five-membered rings and two halogen compounds as leaving groups. Among them, an aromatic cyclopentadienyl group is generally used as a supporting ligand that coordinates with the central metal.

[0009] Such metallocene catalysts are used in various applications including olefin polymerization processes, but the catalyst activity exhibits some limitations (especially in solution processes at temperatures above 100 °C), and it is known that, for example, due to relatively fast chain termination reactions (or chain transfer reactions) such as β-hydride elimination reactions, low molecular weight olefin polymers with a molecular weight (Mn) of 20,000 or less can be prepared at temperatures above 100 °C. In addition, it is known that the active substance of the metallocene catalyst is deactivated at temperatures above 100 °C. Therefore, in order to improve the applicability of metallocene catalysts, methods to overcome the above limitations are needed. Summary of the Invention

[0010] [Technical Problem]

[0011] An object of the present invention is to provide a novel transition metal compound that exhibits excellent copolymerization properties and is capable of preparing olefin polymers, particularly olefin polymers having a high melting temperature and a high molecular weight. The present invention also provides a catalyst composition containing the transition metal compound.

[0012] [Technical Solution]

[0013] To solve the above tasks, the present invention provides a transition metal compound, a catalyst composition, and a method for preparing an olefin polymer.

[0014] (1) The present invention provides a transition metal compound represented by Formula 1.

[0015]

[0016] In Formula 1,

[0017] M is Ti, Zr, or Hf,

[0018] R1 and R9 are represented by the following Formula 2,

[0019] R2 to R8 and R 10 to R 16 are each independently hydrogen, F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms,

[0020] Y is an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 5 to 20 carbon atoms, and

[0021] X1 and X2 are each independently an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms,

[0022]

[0023] In Formula 2,

[0024] R 17 to R 24 are each independently hydrogen, F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, a silylalkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms,

[0025] X is O, S, C(R 25 R 26 ) or N(R 27 ), where R 25 to R 27 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkaryl group having 7 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and

[0026] R 17 to R 24 any one of which is the position connected to Formula 1.

[0027] (2) The present invention provides the transition metal compound as described in (1), wherein, in Formula 1, M is Hf, R2 to R8 and R 10 to R 16 are each independently hydrogen, F or an alkyl group having 1 to 20 carbon atoms, Y is an alkylene group having 1 to 10 carbon atoms, and X1 and X2 are each independently an alkyl group having 1 to 10 carbon atoms.

[0028] (3) The present invention provides the transition metal compound as described in (1) or (2), wherein, in Formula 2, R 17 to R 24 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, R 17 or R 20 is the position connected to Formula 1, X is O, S, C(R 25 R 26 ) or N(R 27 ), where R 25 to R 27 are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.

[0029] (4) The present invention provides the transition metal compound as described in any one of (1) to (3), wherein the transition metal compound represented by Formula 1 is one selected from the group consisting of Formula 1-1 to Formula 1-4.

[0030]

[0031]

[0032]

[0033] In Formulas 1-1 to 1-4,

[0034] M is Ti, Zr, or Hf,

[0035] R3, R6, R 11 and R 14 are each independently F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms,

[0036] Y is an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 5 to 20 carbon atoms,

[0037] X1 and X2 are each independently an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, and

[0038] X is O, S, C(R 25 R 26 ) or N(R 27 ), where R 25 to R 27 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkaryl group having 7 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms.

[0039] (5) The present invention provides a transition metal compound as described in any one of (1) to (4), wherein the transition metal compound represented by Formula 1 is one selected from the group consisting of the following compounds:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] (6) The present invention provides a catalyst composition comprising the transition metal compound described in any one of (1) to (5) and a cocatalyst.

[0047] (7) The present invention provides the catalyst composition as described in (6), wherein the cocatalyst includes one or more selected from the following Formulas 3 to 5:

[0048] [Formula 3]

[0049] -[Al(R a )-O] m -

[0050] [Formula 4]

[0051] D(R a )3

[0052] [Formula 5]

[0053] [L-H] + [Z(A)4] - or [L] + [Z(A)4] -

[0054] In the above formulas,

[0055] R a is independently a halogen group, a hydrocarbon group having 1 to 20 carbon atoms, or a halogenated hydrocarbon group having 1 to 20 carbon atoms,

[0056] m is an integer of 2 or more,

[0057] D is aluminum or boron,

[0058] L is a neutral or cationic Lewis acid,

[0059] Z is an element in Group 13,

[0060] A is independently an aryl group having 6 to 20 carbon atoms in which one or more hydrogen atoms can be substituted by substituents, or an alkyl group having 1 to 20 carbon atoms, and

[0061] the substituents of A are halogen, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms.

[0062] (8) The present invention provides a method for preparing an olefin polymer, the method comprising the step of polymerizing an olefin monomer in the presence of the catalyst composition as described in (6) or (7).

[0063] (9) The present invention provides the method for preparing an olefin polymer as described in (8), wherein the olefin polymer is an ethylene / α-olefin copolymer.

[0064] [Advantageous Effects]

[0065] By using the transition metal compound of the present invention as a catalyst, an olefin polymer having a high melting temperature and a high molecular weight can be easily prepared. Detailed Embodiments

[0066] In the following, the present invention will be described in more detail to facilitate understanding of the present invention.

[0067] It will be understood that the words or terms used in the present invention and the claims should not be construed as having the meanings defined in a commonly used dictionary. It will also be understood that based on the principle that the inventor can appropriately define the meanings of the words or terms to best explain the present invention, the words or terms should be construed as having meanings consistent with their meanings in the technical concept of the present invention.

[0068] Unless otherwise specified, the term "alkyl" as used in this specification refers to a straight-chain, cyclic or branched hydrocarbon residue, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and hexyl, without limitation.

[0069] Unless otherwise specified, the term "cycloalkyl" as used in this specification refers to a non-aromatic cyclic hydrocarbon group composed of carbon atoms. Non-limiting examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.

[0070] Unless otherwise specified, the term "aryl" as used in this specification refers to an optionally substituted benzene ring, or a ring system formed by fusing one or more optional substituents. Examples of optional substituents include substituted C l-3 alkyl, substituted C 2-3 alkenyl, substituted C 2-3 alkynyl, heteroaryl, heterocyclic group, aryl, alkoxy having one to three optional fluorine substituents, aryloxy, aralkyloxy, acyl, aroyl, heteroaroyl, acyloxy, aroyl-oxy, heteroaroyloxy, mercapto, sulfinyl, sulfonyl, sulfamoyl, sulfonylamino, formylamino, carbamoyl, carboxyl, oxo, hydroxy, mercapto, amino, nitro, cyano, halogen or ureido. The ring or ring system may optionally be fused to an aromatic ring (such as a benzene ring), a carbocyclic ring or a heterocyclic ring having one or more optional substituents. Non-limiting examples of the "aryl" group include phenyl, naphthyl, tetrahydronaphthyl, biphenyl, indanyl, anthryl, phenanthryl or their substituted derivatives.

[0071] In the present invention, "alkaryl" means an aryl group substituted by an alkyl group.

[0072] In the present invention, "aralkyl" means an alkyl group substituted by an aryl group.

[0073] Unless otherwise specified, in the present invention, "hydrocarbyl" means a monovalent hydrocarbon group consisting of 1 to 20 carbon atoms composed only of carbon and hydrogen, regardless of its structure, such as alkyl, aryl, alkenyl, alkynyl, cycloalkyl, alkaryl and aralkyl.

[0074] In the present invention, "alkylene" may represent a divalent aliphatic saturated hydrocarbon, such as methylene, ethylene, propylene, and butylene.

[0075] In the present invention, "alkoxy" may include all functional groups, atomic groups, or compounds in which the hydrogen at the end of the alkyl group is replaced by an oxygen atom, such as methoxy, ethoxy, propoxy, and butoxy.

[0076] The transition metal compound of the present invention is characterized by being represented by Formula 1.

[0077]

[0078]

[0079] In Formula 1,

[0080] M is Ti, Zr, or Hf,

[0081] R1 and R9 are represented by the following Formula 2,

[0082] R2 to R8 and R 10 to R 16 are each independently hydrogen, F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms,

[0083] Y is an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 5 to 20 carbon atoms, and

[0084] X1 and X2 are each independently an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms,

[0085]

[0086] In Formula 2,

[0087] R 17 to R 24 are each independently hydrogen, F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms,

[0088] X is O, S, C(R 25 R 26 ) or N(R 27 ), where R 25 to R 27 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkaryl group having 7 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and

[0089] R 17 to R 24 Any one of them is a position connected to Formula 1.

[0090] The transition metal compound of the present invention has a structure in which a condensed ring with a specific structure is substituted at the ortho position of bisphenol, and has a steric hindrance and an electron density difference compared with conventional compounds. Therefore, it is advantageous in terms of the activity of the transition metal compound and the copolymerization property for comonomers.

[0091] Due to the nature of the substituents, the transition metal compound of the present invention can prepare polymers in a high density range and has excellent activity compared with conventional bisphenol compounds. This is an inherent property achieved by the novel structure of the newly developed compound of the present invention.

[0092] In particular, in Formula 1, M can be Hf.

[0093] Specifically, in Formula 1, R2 to R8 and R 10 to R 16 can each independently be hydrogen, F, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.

[0094] In particular, in Formula 1, Y can be an alkylene group having 1 to 10 carbon atoms, an alkylene group having 1 to 6 carbon atoms, or an alkylene group having 1 to 4 carbon atoms, such as propylene.

[0095] In particular, in Formula 1, X1 and X2 can each independently be an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms, such as methyl.

[0096] In particular, in Formula 2, R 17 or R 20 can be a position connected to Formula 1.

[0097] In particular, in Formula 2, R 17 to R 24 (except for the position connected to Formula 1) can each independently be hydrogen or an alkyl group having 1 to 10 carbon atoms, such as hydrogen.

[0098] In particular, in Formula 2, X can be O, S, C(R 25 R 26 ) or N(R 27 ), where R 25 to R 27 each independently is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, R 25 and R 26 can each independently be an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 3 carbon atoms, such as methyl, and R27 It may be an aryl group having 6 to 10 carbon atoms, such as a phenyl group.

[0099] In particular, the transition metal compound represented by Formula 1 may be a transition metal compound selected from the group consisting of the following Formulas 1-1 to 1-4.

[0100]

[0101]

[0102] In Formulas 1-1 to 1-4, M is Ti, Zr, or Hf.

[0103] R3, R6, R 11 and R 14 are each independently F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.

[0104] Y is an alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 5 to 20 carbon atoms.

[0105] X1 and X2 are each independently an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, and

[0106] X is O, S, C(R 25 R 26 ) or N(R 27 ), where R 25 to R 27 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkaryl group having 7 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms.

[0107] The transition metal compound represented by Formula 1 may be one selected from the group consisting of the following compounds, but the present invention may include all transition metal compounds corresponding to Formula 1 without limitation.

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] The catalyst composition of the present invention is characterized by comprising a transition metal compound represented by Formula 1 and a cocatalyst.

[0115] In the present invention, "composition" includes the material containing the composition and the mixture of reaction products and decomposition products obtained from the material of the composition.

[0116] In addition, the catalyst composition of the present invention may further comprise a cocatalyst.

[0117] As the cocatalyst, those known in the art can be used. For example, one or more selected from the group consisting of Formulas 4 to 6 can be used as the cocatalyst.

[0118] [Formula 4]

[0119] -[Al(R a )-O] m -

[0120] [Formula 5]

[0121] D(R a )3

[0122] [Formula 6]

[0123] [L-H] + [Z(A)4] - or [L] + [Z(A)4] -

[0124] In the above formulas,

[0125] R a each independently represents a halogen group, a hydrocarbon group having 1 to 20 carbon atoms, or a halogenated hydrocarbon group having 1 to 20 carbon atoms,

[0126] m is an integer of 2 or more,

[0127] D is aluminum or boron,

[0128] L is a neutral or cationic Lewis acid,

[0129] Z is an element in Group 13,

[0130] A each independently represents an aryl group having 6 to 20 carbon atoms in which one or more of the hydrogen atoms can be substituted by a substituent, or an alkyl group having 1 to 20 carbon atoms, and

[0131] the substituent of A is a halogen group, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms.

[0132] The compound represented by Formula 4 is not particularly limited as long as it is an alkylaluminoxane. Preferred examples may include methylaluminoxane, ethylaluminoxane, isobutylaluminoxane, butylaluminoxane, etc., and methylaluminoxane is particularly preferred.

[0133] The compound represented by Formula 5 is not particularly limited, and preferred examples thereof may include trimethylaluminum, triethylaluminum, triisobutylaluminum, tripropylaluminum, tributylaluminum, dimethylaluminum chloride, tri-sec-butylaluminum, tricyclopentylaluminum, tripentylaluminum, triisopentylaluminum, trihexylaluminum, trioctylaluminum, ethyldimethylaluminum, methyldiethylaluminum, triphenylaluminum, tri-p-tolylaluminum, dimethylmethoxyaluminum, dimethylethoxyaluminum, trimethylboron, triethylboron, triisobutylboron, tripropylboron, tributylboron, etc., and is particularly preferably selected from trimethylaluminum, triethylaluminum, and triisobutylaluminum.

[0134] If Z is boron, examples of the compound represented by Formula 6 may include, for example, di(octadecyl)methylammonium tetrakis(pentafluorophenyl)borate ([(C 18 H 37 )2N(H)Me] + [B(C6F5)4] - ), di(octadecyl)methylammonium tetraphenylborate, di(octadecyl)methylammonium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, triethylammonium tetraphenylborate, tributylammonium tetraphenylborate, trimethylammonium tetraphenylborate, tripropylammonium tetraphenylborate, trimethylammonium tetrakis(p-tolyl)borate, trimethylammonium tetrakis(o,p-dimethylphenyl)borate, tributylammonium tetrakis(p-trifluoromethylphenyl)borate, trimethylammonium tetrakis(p-trifluoromethylphenyl)borate, tributylammonium tetrakis(pentafluorophenyl)borate, N,N-diethylbenzammonium tetraphenylborate, N,N-diethylbenzammonium tetrakis(pentafluorophenyl)borate, diethylammonium tetrakis(pentafluorophenyl)borate, triphenylphosphonium tetraphenylborate, trimethylphosphonium tetraphenylborate, triphenylammonium tetrakis(p-tolyl)borate, triethylammonium tetrakis(o,p-dimethylphenyl)borate, triphenylcarbenium tetrakis(p-trifluoromethylphenyl)borate, triphenylcarbenium tetrakis(pentafluorophenyl)borate, or a combination thereof. If Z is boron, examples of the compound represented by Formula 6 may include, for example, triethylammonium tetraphenylaluminum, tributylammonium tetraphenylaluminum, trimethylammonium tetraphenylaluminum, tripropylammonium tetraphenylaluminum, trimethylammonium tetrakis(p-tolyl)aluminum, tripropylammonium tetrakis(p-tolyl)aluminum, triethylammonium tetrakis(o,p-dimethylphenyl)aluminum, tributylammonium tetrakis(p-trifluoromethylphenyl)aluminum, trimethylammonium tetrakis(p-trifluoromethylphenyl)aluminum, tributylammonium tetrakis(pentafluorophenyl)aluminum, N,N-diethylbenzammonium tetraphenylaluminum, N,N-diethylbenzammonium tetrakis(pentafluorophenyl)aluminum, diethylammonium tetrakis(pentafluorophenyl)aluminum, triphenylphosphonium tetraphenylaluminum, trimethylphosphonium tetraphenylaluminum, triethylammonium tetraphenylaluminum, tributylammonium tetraphenylaluminum, or a combination thereof, without limitation.

[0135] In particular, the cocatalyst used in the present invention may be a compound represented by Formula 6, especially bis(octadecyl)methylammonium tetrakis(pentafluorophenyl)borate.

[0136] In addition, the transition metal compound represented by Formula 1 and the cocatalyst may be used in a supported form via a carrier. Silica or alumina may be used as the carrier without limitation.

[0137] The method for preparing an olefin polymer of the present invention is characterized by including a step of polymerizing an olefin monomer in the presence of a catalyst composition.

[0138] In the present invention, "polymer" refers to a polymer compound prepared by polymerizing the same or different types of monomers. Thus, the general term "polymer" includes the term "homopolymer" used to represent a polymer prepared from only one type of monomer and the term "interpolymer" described below.

[0139] In the present invention, the term "interpolymer" refers to a polymer prepared by polymerizing at least two different types of monomers. Thus, the general term "interpolymer" refers to a polymer prepared from two different types of monomers and includes the commonly used copolymer and a polymer prepared from more than two different types of monomers.

[0140] In the present invention, the olefin monomer may be one or more selected from the group consisting of ethylene, propylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-undecene, 1-dodecene, 1-tetradecene, 1-hexadecene, and 1-eicosene without limitation.

[0141] In particular, depending on the type of the olefin monomer, the olefin polymer of the present invention may be an olefin homopolymer or an olefin-α-olefin copolymer, and preferably, it may be an ethylene / α-olefin copolymer. In this case, the content of the α-olefin monomer (i.e., comonomer) may be appropriately selected by those skilled in the art according to the use, purpose, etc. of the olefin polymer, and may be about 1 to 99 mol%.

[0142] The catalyst composition may be dissolved or diluted in the following solvents applicable to the olefin polymerization process and then injected: aliphatic hydrocarbon solvents having 5 to 12 carbon atoms (such as pentane, hexane, heptane, nonane, decane, and their isomers), aromatic hydrocarbon solvents (such as toluene and benzene), or hydrocarbon solvents substituted with chlorine atoms (such as dichloromethane and chlorobenzene). The solvents used herein may preferably be used after treating with a small amount of alkylaluminum to remove a small amount of water or air as a catalyst poison, and may also be treated by using a cocatalyst.

[0143] The most preferred preparation method of the catalyst composition is a solution process, and if the composition is used together with an inorganic carrier such as silica, it can also be applied to a slurry process or a gas phase process.

[0144] Polymerization can be carried out by homopolymerizing one olefin monomer or copolymerizing two or more olefin monomers by using one of a continuous slurry polymerization reactor, a loop slurry reactor, a gas phase reactor, or a solution reactor.

[0145] In addition, in order to remove moisture in the reactor during the polymerization reaction, an organoaluminum compound can also be injected, and the polymerization reaction can be carried out in its presence. Specific examples of such organoaluminum compounds can include trialkylaluminum, dialkylaluminum halide, alkylaluminum dihalide, dialkylaluminum hydride, or sesquialuminum halide, and more specific examples can include Al(C2H5)3, Al(C2H5)2H, Al(C3H7)3, Al(C3H7)2H, Al(i-C4H9)2H, Al(C8H 17 )3, Al(C 12 H 25 )3, Al(C2H5)(C 12 H 25 )2, Al(i-C4H9)(C 12 H 25 )2, Al(i-C4H9)2H, Al(i-C4H9)3, (C2H9)2AlCl, (i-C4H9)2AlCl, or (C2H5)3Al2Cl3. Such organoaluminum compounds can be continuously injected into the reactor, or can be injected at a ratio of about 0.1 to 10 mol per 1 kg of the reaction medium, and are injected into the reactor to appropriately remove moisture.

[0146] According to an embodiment of the present invention, the polymerization of the olefin polymer can be carried out at a temperature of about 80 °C to 200 °C, particularly at a temperature of about 90 °C to 200 °C, or at a temperature of about 130 °C to 200 °C and a pressure of about 20 to 100 bar, particularly at a pressure of about 20 to 50 bar, or at a pressure of about 20 to 40 bar for about 8 minutes to 2 hours.

[0147] Examples

[0148] Hereinafter, the present invention will be explained in more detail with reference to examples. However, the examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0149] Preparation of transition metal compound

[0150] Preparation Example 1

[0151]

[0152] The compound was prepared according to the following protocol.

[0153]

[0154] (1) Preparation of Compound 1-1

[0155] 2-Bromo-4-(tert-butyl)phenol (15.0 g, 65.5 mmol) was dissolved in 100 mL of N,N-dimethylformamide and cooled to below 0 °C using an ice bath. NaH (2.9 g, 72 mmol) was slowly injected therein, and the temperature was raised to room temperature. After stirring for 30 minutes at room temperature, the temperature was lowered to 0 °C again, and chloromethyl methyl ether (5.80 g, 72 mmol) was injected therein. The temperature was raised to room temperature and stirred for 3 hours. After completion of the reaction, 500 mL of water was injected and extraction with ethyl acetate was carried out. The separated organic layer was washed twice with 300 mL of water, separated and slurried with anhydrous magnesium sulfate. After filtration, the resulting product was concentrated under reduced pressure to prepare Compound 1-1 in the form of an oil (17 g, yield 95%).

[0156] (2) Preparation of Compound 1-2

[0157] Compound 1-1 (7.0 g, 25.6 mmol) and dibenzo[b,d]furan-1-ylboronic acid (5.7 g, 26.9 mmol) were dissolved in 85 mL of tetrahydrofuran, 30 mL of an aqueous potassium carbonate solution (10.6 g, 77 mmol) was injected therein, and then heated. Under reflux, tetrakis(triphenylphosphine)palladium (0.15 g, 0.13 mmol) was injected into the mixture thus obtained, and then refluxed and stirred for 12 hours. After completion of the reaction, the temperature was lowered to room temperature, and tetrahydrofuran was removed by concentration under reduced pressure. The mixture thus obtained was dissolved by injecting ethyl acetate, and the resulting product was washed twice with water. The organic layer was separated and treated with anhydrous magnesium sulfate. After filtration, the organic layer was concentrated under reduced pressure. The resulting product was slurried with a small amount of tert-butyl methyl ether and an excess of hexane, stirred at room temperature for 2 hours and filtered to prepare the target Compound 1-2 in dark gray (9.0 g, yield 97%).

[0158] (3) Preparation of Compound 1-3

[0159] Compound 1-2 (6.63 g, 18.4 mmol) was dissolved in 40 mL of anhydrous tetrahydrofuran and cooled to -20 °C. n-Butyllithium was slowly injected into it. The temperature was raised to room temperature, stirred for 2 hours, and triisopropyl borate (4.7 mL, 20.2 mmol) was injected into it. After stirring at room temperature for about 1 hour and completing the reaction, 50 mL of 1N aqueous HCl solution was injected and stirred. The resulting product was extracted with ethyl acetate, the organic layer was separated, and the organic layer was washed with water again, separated and treated with anhydrous magnesium sulfate. After filtration, the organic layer was concentrated under reduced pressure. The target compound 1-3 (6.3 g, 84.7%) in the form of a mixture of a yellow foam and an oil was prepared.

[0160] (4) Preparation of Compound 1-4

[0161] Compound 2-bromo-4-fluorophenol (10.0 g, 52.4 mmol) and 1,3-dibromopropane (5.3 g, 26.2 mmol) were dissolved in 150 mL of acetone, potassium carbonate (21.7 g, 157 mmol) was injected into it, and then heated. After stirring at reflux for 12 hours, the resulting product was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure, the concentrated compound was redissolved in ethyl acetate, and washed twice with water. The organic layer was separated and slurried with anhydrous magnesium sulfate. After filtration, the organic layer was concentrated under reduced pressure. A small amount of hexane was added to the concentrated compound and slurried, and filtered to obtain Compound 1-4 (8.3 g, yield 75.1%) as a white solid.

[0162] (5) Preparation of Compound 1-5

[0163] Compound 1-3 (6.3 g, 15.6 mmol) and Compound 1-4 (3.0 g, 7.1 mmol) were diluted in 50 mL of 1,4-dioxane, and 20 mL of aqueous potassium carbonate solution (3.9 g, 28.4 mmol) was injected into it. The mixture was heated, and at reflux, tetrakis(triphenylphosphine)palladium(0) (0.16 g, 0.14 mmol) was injected, and then refluxed and stirred for 12 hours. After completing the reaction, the temperature was lowered to room temperature, ethyl acetate was injected into it, washed twice with water, the organic layer was separated and treated with anhydrous magnesium sulfate. After filtration, the organic layer was concentrated under reduced pressure. The concentrated compound was separated by column using silica gel column chromatography to prepare the target compound 1-5 (2.0 g, yield 28.7%) in the form of a white solid.

[0164] (6) Preparation of Compound 1-6

[0165] Compound 1-5 (2.0 g, 2.04 mmol) was injected into methanol. While stirring, 0.5 mL of concentrated hydrochloric acid was injected into it, and then it was heated. While refluxing, it was stirred for more than 12 hours, then the temperature was lowered to room temperature, and the pH was adjusted to 7 - 8 using saturated aqueous sodium bicarbonate solution, and extraction was carried out using ethyl acetate. The extracted organic layer was washed with water once more and slurried with anhydrous magnesium sulfate. After filtration, the organic layer was concentrated under reduced pressure. The obtained product was separated by column chromatography using a mixture solution of hexane and ethyl acetate mixed at 5 / 1 to prepare the target compound 1-6 (1.13 g, yield 62%).

[0166] (7) Preparation of Compound 1

[0167] In a glove box, Compound 1-6 (1.0 g, 1.1 mmol) and hafnium tetrachloride (0.36 g, 1.1 mmol) were diluted in 25 mL of toluene, and a 3.0 M solution of methylmagnesium bromide (1.5 mL, 4.5 mmol) was slowly injected. After stirring for 12 hours, 10 mL of hexane was injected into the mixture, and it was stirred for about 3 hours and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure, 20 mL of a solution of toluene and hexane mixed at 1 / 1 was injected into the concentrate and slurried for 3 hours. After filtration, the filtrate was concentrated under reduced pressure to prepare Compound 1 as a white solid (0.9 g, yield 73%).

[0168] 1 H NMR (500 MHz, C6D6): 8.33 (d, 2H), 8.08 (s, 4H), 7.37 (d, 2H), 7.05 (d, 2H), 7.58 - 7.49 (m, 4H), 7.35 - 7.25 (m, 4H), 7.19 - 7.05 (m, 6H), 4.50 - 4.38 (m, 4H), 3.67 - 3.40 (m, 2H), 1.52 (s, 9H), 1.38 (s, 9H), 0.91 (s, 6H)

[0169] Preparation Example 2

[0170]

[0171] The compound was prepared according to the following scheme.

[0172]

[0173] (1) Preparation of Compound 2-1

[0174] The target compound 2-1 (6.1 g, yield 98.7%) was prepared in the same manner as in the preparation example for preparing Compound 1-1 using 2-bromo-4-methylphenol (5.0 g, 26.7 mmol).

[0175] (2) Preparation of Compound 2-2

[0176] The target compound 2-2 (14.5 g, yield 97.3%) as a yellow oil was prepared by carrying out in the same manner as in the preparation example of compound 1-2, using compound 2-1 (10 g, 43.3 mmol) and (9,9-dimethyl-9H-fluoren-4-yl)boronic acid (10.8 g, 45.4 mmol).

[0177] (3) Preparation of Compound 2-3

[0178] Compound 2-3 was prepared by carrying out in the same manner as in the preparation example of compound 1-3, using compound 2-2 (15.5 g, 48.8 mmol), and was separated by column chromatography using a mixed solvent of hexane and ethyl acetate in a ratio of 10 / 1 to prepare compound 2-3 as a white solid (9.6 g, yield 50.6%).

[0179] (4) Preparation of Compound 2-4

[0180] Compound 2-4 was prepared by carrying out in the same manner as in the preparation example of compound 1-5, using compound 2-3 (4.6 g, 11.9 mmol) and compound 1-4 (2.0 g, 4.7 mmol), and was separated by column chromatography using a mixed solvent of hexane and ethyl acetate in a ratio of 20 / 1 to prepare compound 2-4 as a white solid (3.02 g, yield 66.7%).

[0181] (5) Preparation of Compound 2-5

[0182] The target compound 2-5 (1.1 g, yield 36.7%) as a light yellow solid was prepared by carrying out in the same manner as in the preparation example of compound 1-6, using compound 2-4 (3.0 g, 3.16 mmol).

[0183] (6) Preparation of Compound 2

[0184] In a glove box, compound 2-4 (1.16 g, 1.3 mmol) and hafnium tetrachloride (0.43 g, 1.35 mmol) were diluted in 30 ml of toluene, and a 3.0 M methylmagnesium bromide solution (1.8 ml, 5.4 mmol) was slowly injected. After stirring for 12 hours, 10 mL of hexane was injected into the mixture, stirred for about 3 hours, and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure, and a solution of 20 mL of toluene and hexane mixed in a ratio of 1 / 1 was injected into the concentrate and slurried for 3 hours. After filtration, the filtrate was concentrated under reduced pressure to prepare compound 2 as a white solid (1.35 g, yield 91%).

[0185] 11H NMR (500 MHz, CDCl3): 7.75 - 7.83 (d, 1H), 7.54 - 6.93 (m, 21H), 6.58 (m, 1H), 6.41 (m, 1H), 5.52 (m, 1H), 5.08 (m, 1H), 3.99 - 3.92 (m, 1H), 3.69 - 3.52 (m, 2H), 3.31 - 3.23 (m, 1H), 2.35 (m, 6H), 2.27 (m, 3H), 1.61 (m, 6H), 1.44 (t, 3H), 1.26 (s, 3H), -0.80 (s, 6H)

[0186] Preparation Example 3

[0187]

[0188] The compound was prepared according to the following scheme.

[0189]

[0190] (1) Preparation of Compound 3-1

[0191] The target compound 3-1 (6.21 g, yield 73%) as a white solid was prepared by carrying out in the same manner as in the preparation example of Compound 1-2, using Compound 2-1 (5 g, 21.6 mmol) and (9-phenyl-9H-carbazol-1-yl)boronic acid (6.5 g, 22.7 mmol).

[0192] (2) Preparation of Compound 3-2

[0193] The target compound 3-2 (2.52 g, yield 65%) as a white solid was prepared by carrying out in the same manner as in the preparation example of Compound 1-3, using Compound 3-1 (3.5 g, 8.9 mmol).

[0194] (3) Preparation of Compound 3-3

[0195] Compound 3-3 (5.84 g, yield 88%) as a white solid was prepared by carrying out in the same manner as in the preparation example of Compound 1-4, using 2-bromo-4-methylphenol (6.0 g, 32.1 mmol).

[0196] (4) Preparation of Compound 3-4

[0197] The target compound 3-4 (4.01 g, yield 75%) in light gray was prepared by carrying out in the same manner as in the preparation example of Compound 1-5, using Compound 3-2 (5.0 g, 11.4 mmol) and Compound 3-3 (2.13 g, 5.15 mmol).

[0198] (5) Preparation of Compound 3-5

[0199] The target compound 3-5 was prepared as a white solid in the same manner as in the preparation example of Compound 1-6, using Compound 3-4 (5.0 g, 4.81 mmol) (3.52 g, yield 77%).

[0200] (6) Preparation of Compound 3

[0201] In the glove box, the target compound 3 (0.45 g, yield 49%) was prepared as a white solid in the same manner as in the preparation example of Compound 1, using Compound 3-5 (1.10 g, 1.16 mmol).

[0202] 1 H NMR (500 MHz, C6D6): 8.65 (d, 1H), 8.55 (d, 1H), 8.42 (d, 1H), 8.29 (d, 1H), 8.19 (d, 1H), 8.06 (d, 1H), 7.94 (d, 1H), 7.78 (s, 2H), 7.71 (s, 4H), 7.62 - 7.50 (m, 12H), 7.48 - 7.20 (m, 5H), 7.16 (t, 2H), 7.10 (d, 2H), 3.92 (t, 4H), 2.46 (s, 6H), 2.36 (s, 6H), 2.13 (m, 2H), 0.9 (s, 6H)

[0203] Preparation Example 4

[0204]

[0205] Compounds were prepared according to the following scheme.

[0206]

[0207] (1) Preparation of Compound 4-1

[0208] The target compound 4-1 (5.28 g, yield 73%) was prepared in the same manner as in the preparation example of Compound 1-2, using Compound 2-1 (5.0 g, 21.6 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (5.18 g, 22.7 mmol).

[0209] (2) Preparation of Compound 4-2

[0210] The target compound 4-2 (3.84 g, yield 68%) was prepared in the same manner as in the preparation example of Compound 1-3, using Compound 4-1 (5.0 g, 15.0 mmol).

[0211] (3) Preparation of Compound 4-3

[0212] 4-(2,4,4-Trimethylpentan-2-yl)phenol (10.0 g, 48.5 mmol) was dissolved in 50 mL of N,N-dimethylformamide and cooled to 0 °C. N-Bromosuccinimide (8.63 g, 48.5 mmol) was injected therein, and the mixture was stirred at the same temperature for 1 hour. Thereafter, the reaction mixture was poured into 500 mL of water. The resulting product was extracted with dichloromethane solvent, the organic layer was separated, and the organic layer was washed again with 500 mL of water. The separated organic layer was slurried with anhydrous magnesium sulfate and stirred. After filtration, the filtrate was concentrated under reduced pressure. The oily concentrate was slurried with ethyl acetate and hexane and filtered to prepare the target compound 4-3 (11.2 g, yield 81%) as a white solid.

[0213] (4) Preparation of Compound 4-4

[0214] The target compound 4-4 (6.5 g, yield 76%) was prepared by performing the same manner as in the preparation example of Compound 1-4, using Compound 4-3 (8.0 g, 28.1 mmol) and 1,3-dibromopropane (2.83 g, 14.0 mmol).

[0215] (5) Preparation of Compound 4-5

[0216] The target compound 4-5 (6.0 g, yield 77%) as a white solid was prepared by performing the same manner as in the preparation example of Compound 1-5, using Compound 4-2 (5.3 g, 14.0 mmol) and Compound 4-4 (4.3 g, 7.1 mmol).

[0217] (6) Preparation of Compound 4-6

[0218] The target compound 4-6 (3.8 g, yield 91%) was prepared by performing the same manner as in the preparation example of Compound 1-6, using Compound 4-5 (4.5 g, 4.0 mmol).

[0219] (7) Preparation of Compound 4

[0220] In a glove box, the target compound 4 (0.61 g, yield 65%) as a white solid was prepared by performing the same manner as in the preparation example of Compound 1, using Compound 4-6 (0.78 g, 0.76 mmol).

[0221] 11H NMR (500 MHz, CDCl3): δ 8.63 (d, 2H), 8.42 (d, 2H), 8.34 (d, 2H), 7.97 (d, 2H), 7.83 (s, 2H), 7.70 (s, 4H), 7.66 (s, 2H), 7.60 (d, 2H), 7.51 (t, 2H), 7.45 (t, 2H), 7.03 (d, 2H), 4.05 (t, 4H), 2.42 (s, 6H), 2.36 (s, 6H), 2.13 (m, 2H), 1.36 (s, 4H), 0.91 (s, 30H), 0.89 (s, 6H)

[0222] Comparative Preparation Example 1

[0223]

[0224] The compound was prepared according to the following scheme.

[0225]

[0226] (1) Preparation of Compound C1-2

[0227] The target compound C1-2 (5.4 g, yield 97%) was prepared by carrying out the same manner as in the preparation example of Compound 1-3, using Compound C1-1 (5.0 g, 13.1 mmol).

[0228] (2) Preparation of Compound C1-3

[0229] The target compound 4-5 (1.2 g, yield 24.8%) as a white solid was prepared by carrying out the same manner as in the preparation example of Compound 1-5, using Compound C1-2 (4.42 g, 10.4 mmol) and Compound 4-4 (2.0 g, 4.7 mmol).

[0230] (3) Preparation of Compound C1-4

[0231] Compound C1-3 (5.6 g, 4.7 mmol) was dissolved in a mixed solution of 15 mL of methanol and tetrahydrofuran in a 1 / 1 ratio. p-Toluenesulfonic acid (2.0 g, 4.7 mmol) was injected into it at room temperature, and then the mixture was heated to 50 °C. After completion of the reaction, the mixture solution was cooled to room temperature, concentrated under reduced pressure to remove the solvent, diluted again in ethyl acetate and washed twice with water. The organic layer was separated and slurried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The concentrated compound was separated by column chromatography using a solvent mixture of hexane and ethyl acetate in a 2 / 1 ratio to prepare the target compound C1-4 (1.2 g, yield 30%) as a white solid.

[0232] (4) Preparation of Compound C1

[0233] The target compound C1 (0.3 g, yield 24.1%) as a white solid was prepared in the same manner as in the preparation example of Compound 1, using Compound C4 (1.0 g, 1.2 mmol).

[0234] Comparative Preparation Example 2

[0235]

[0236] The compound was prepared according to the following scheme.

[0237]

[0238] (1) Preparation of Compound C2-1

[0239] Compound 2-1 (5.0 g, 21.6 mmol) and carbazole (3.12 g, 22.7 mmol) were dissolved in 50 mL of toluene. CuI (4.33 g, 21.6 mmol), 1,10-phenanthroline (0.82 g, 4.54 mmol), and cesium carbonate (14.1 g, 43.2 mmol) were injected therein, and then the mixture was heated, refluxed, and stirred. After completion of the reaction, the resulting solution was filtered through a diatomaceous earth pad, and the filtrate was concentrated under reduced pressure. The mixture thus obtained was slurried with a mixed solvent of hexane and ethyl acetate in a ratio of 4 / 1 to prepare the target compound C2-1 (4.7 g, yield 68%) as a light red solid.

[0240] (2) Preparation of Compound 2-2

[0241] The target compound C2-2 (21 g, yield 99%) was prepared in the same manner as in the preparation example of Compound 1-3, using Compound C2-1 (18.7 g, 58.9 mmol).

[0242] (3) Preparation of Compound C2-3

[0243] The target compound C2-3 (7.0 g, yield 82%) was prepared in the same manner as in the preparation example of Compound 1-5, using Compound C2-2 (7.53 g, 20.9 mmol) and Compound 4-4 (4.0 g, 9.5 mmol).

[0244] (4) Preparation of Compound C2-4

[0245] The target compound C2-4 (0.8 g, yield 88.7%) as a white solid was prepared in the same manner as in the preparation example of Compound 1-6, using Compound C2-3 (1.0 g, 1.1 mmol).

[0246] (5) Preparation of Compound C2

[0247] The target compound C2 (0.9 g, yield 71.6%) as a white solid was prepared in the same manner as in the preparation example of Compound 1, using Compound C2-4 (1.0 g, 1.2 mmol).

[0248] Polymerization of ethylene / α-olefin copolymer

[0249] Example 1

[0250] Hexane solvent (900 mL) and 1-octene (300 mL) were added to a 2 L autoclave reactor, and the temperature of the reactor was preheated to 150 °C. At the same time, the reactor was pressurized with ethylene (35 bar) in advance. By applying a high-pressure argon pressure, 3 μmol of the catalyst of Preparation Example 1, 30 μmol of dimethylanilinium tetrakis(pentafluorophenyl)borate cocatalyst (AB) relative to 10 equivalents of the catalyst, and 0.6 mmol of triisobutylaluminum as a scavenger were successively added to the reactor, and the copolymerization reaction was carried out for 8 minutes. Then, the remaining ethylene gas was discharged, and the polymer solution was added to an excess of ethanol to induce precipitation. The precipitated polymer was washed with ethanol two or three times and dried in a vacuum oven at 90 °C for more than 12 hours.

[0251] Examples 2 to 4 and Comparative Examples 1 and 2

[0252] Ethylene / α-olefin copolymers were prepared by the same method as in Example 1, except that the catalyst type was changed according to Table 1.

[0253] [Table 1]

[0254] Mixed catalyst Example 1 Preparation Example 1 Example 2 Preparation Example 2 Example 3 Preparation Example 3 Example 4 Preparation Example 4 Comparative Example 1 Comparative Preparation Example 1 Comparative Example 2 Comparative Preparation Example 2

[0255] Analysis of the preparation results of ethylene / α-olefin copolymers

[0256] Experimental Example 1

[0257] The physical properties of the copolymers prepared in the examples and comparative examples were analyzed comparatively. The measurement conditions and methods are as follows.

[0258] (1) Catalyst activity (kgPE) / mmol)

[0259] The obtained polymer was dried in vacuo, the yield was measured, and the value obtained by dividing the polymer (kg) by the catalyst (mmol) was calculated.

[0260] (2) Density

[0261] Measurement was carried out according to ASTM D-792.

[0262] (3) Melting temperature (Tm)

[0263] The melting temperature (Tm) can be obtained using a differential scanning calorimeter (DSC 6000) manufactured by PerkinElmer. In particular, for the copolymer, using DSC in a nitrogen atmosphere, the temperature is raised to 150 °C, held for 5 minutes, cooled to -100 °C, and then raised again while observing the DSC curve. In this case, the heating rate and the cooling rate are each 10 °C / minute.

[0264] On the measured DSC curve, the melting temperature is set to the maximum point of the endothermic peak during the second heating process.

[0265] [Table 2]

[0266]

[0267] As shown in Table 2, by using the transition metal compound of Formula 1 as a catalyst, compared with the conventional compound of Comparative Example 1, a polymer in a high density range can be prepared and the catalyst activity is excellent, and compared with the compound of Comparative Example 2, a polymer in a high density range can be prepared. This shows that by using the transition metal compound represented by Formula 1 developed in the present invention as a catalyst, a polyolefin having a high density can be produced with high productivity.

Claims

1. A transition metal compound represented by the following formula 1: [Formula 1] In Formula 1, M is Ti, Zr or Hf, R1 and R9 are represented by the following formula 2, R2 to R8 and R 10 to R 16 each independently is hydrogen, F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, a alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, Y is an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 5 to 20 carbon atoms, and X1 and X2 are each independently an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms: [Formula 2] In Formula 2, R 17 to R 24 each independently is hydrogen, F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, a alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, X is O, S, C(R 25 R 26 ) or N(R 27 ), where each of R 25 to R 27 is independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkaryl group having 7 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and R 17 to R 24 Any one of them is a position connected to Formula 1.

2. The transition metal compound according to claim 1, wherein, In Formula 1, M is Hf, R2 to R8 and R 10 to R 16 are each independently hydrogen, F or an alkyl group having 1 to 20 carbon atoms, Y is an alkylene group having 1 to 10 carbon atoms, and X1 and X2 are each independently an alkyl group having 1 to 10 carbon atoms.

3. The transition metal compound according to claim 1, wherein, In Formula 2, R 17 to R 24 each independently represents hydrogen or an alkyl group having 1 to 10 carbon atoms, R 17 or R 20 is a position connected to Formula 1 X is O, S, C(R 25 R 26 ) or N(R 27 ), where R 25 to R 27 are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.

4. The transition metal compound according to claim 1, wherein The transition metal compound represented by Formula 1 is one selected from the group consisting of Formula 1-1 to Formula 1-4: [Formula 1-1] [Formula 1-2] [Formula 1-3] [Formula 1-4] In Formula 1-1 to Formula 1-4, M is Ti, Zr or Hf, R3, R6, R 11 and R 14 each independently is F, Cl, CN, CF3, an alkyl group having 1 to 20 carbon atoms, a alkylsilyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, Y is an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 5 to 20 carbon atoms, X1 and X2 are each independently an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, and X is O, S, C(R 25 R 26 ) or N(R 27 ), where each of R 25 to R 27 is independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkaryl group having 7 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms.

5. The transition metal compound according to claim 1, wherein, The transition metal compound represented by Formula 1 is one selected from the group consisting of the following compounds:

6. A catalyst composition comprising the transition metal compound according to claim 1 and a cocatalyst.

7. The catalyst composition according to claim 6, wherein, The cocatalyst includes one or more selected from the group consisting of the following Formula 3 to Formula 5: [Formula 3] -[Al(R a )-O] m - [Formula 4] D(R a )3 [Formula 5] [L-H] + [Z(A)4] - or [L] + [Z(A)4] - In the above formula, R a each independently represents a halogen group, a hydrocarbon group having 1 to 20 carbon atoms, or a halogenated hydrocarbon group having 1 to 20 carbon atoms m is an integer of 2 or more, D is aluminum or boron, L is a neutral or cationic Lewis acid, Z is an element in Group 13, A is each independently an aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms in which one or more hydrogen atoms can be substituted by a substituent, and The substituent of A is a halogen, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms.

8. A method for preparing an olefin polymer, the method comprising the step of polymerizing an olefin monomer in the presence of the catalyst composition according to claim 6 or 7.

9. The method for preparing an olefin polymer according to claim 8, wherein, The olefin polymer is an ethylene / α-olefin copolymer.

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