Transition metal compounds and catalyst compositions containing the same

Abstract

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

Description

[Technical Field]

[0001] This application claims the benefit of priority based on Korean Patent Application No. 10-2023-0021372, filed February 17, 2023, the entire contents of which are incorporated herein by reference. The present invention relates to a transition metal compound having a novel structure and a catalyst composition containing the same. [Background technology]

[0002] Generally, olefin polymers such as ethylene copolymers are useful polymeric materials used as materials for blow moldings, extrusion moldings, films, sheets, etc., and have been produced in the presence of Ziegler-Natta catalyst systems.

[0003] The Ziegler-Natta catalyst is a heterogeneous catalyst, which is used in systems where the reactant phase and the catalyst phase are not the same, such as a liquid-phase reactant-solid catalyst system. Such Ziegler-Natta catalysts are composed of two components, typically transition metals such as titanium (Ti), vanadium (V), chromium (Cr), molybdenum (Mo), and zirconium (Zr), along with halogen compounds (e.g., TiCl4), alkyl lithium, and alkyl aluminum.

[0004] However, the Ziegler-Natta catalyst has the drawback that the concentration of active species is only a few percent to several tens of percent relative to the transition metal atoms, and most of the transition metal atoms are unable to exert their function, making it impossible to overcome the limitations of heterogeneous catalysts.

[0005] In recent years, metallocene compounds have been attracting attention as next-generation catalysts that can overcome these drawbacks. Metallocene compounds are homogeneous catalysts containing Group 4 metals and are known to exhibit favorable polymerization activity in olefin polymerization.

[0006] Most metallocene catalysts used in polymerization are based on a Group 4 metal element such as titanium, zirconium, or hafnium (Hf) and a supporting ligand, which consists of two aromatic five-atom rings and two halogen compounds as leaving groups. Of these, the supporting ligand coordinated to the central metal is typically an aromatic cyclopentadienyl group.

[0007] Metallocene catalysts are widely used in olefin polymerization processes, but they exhibit limitations in catalytic activity (especially in solution processes at temperatures above 100°C). For example, due to relatively fast end-capping reactions (or chain reactions) such as the beta-hydride elimination reaction, they are generally only capable of producing low-molecular-weight olefin polymers with molecular weights (Mn) of 20,000 or less at temperatures above 100°C. Furthermore, it is known that the active species of metallocene catalysts tend to become inactive at temperatures above 100°C. Therefore, in order to increase the applicability of metallocene catalysts, a method to overcome these limitations is needed. Summary of the Invention [Problem to be solved by the invention]

[0008] An object of the present invention is to provide a novel transition metal compound which exhibits excellent copolymerizability and is capable of producing an olefin polymer, particularly an olefin polymer having a high melting temperature and a high molecular weight, and a catalyst composition containing the same. [Means for solving the problem]

[0009] In order to solve the above problems, the present invention provides a transition metal compound, a catalyst composition, and a method for producing an olefin polymer. (1) The present invention provides a transition metal compound represented by the following chemical formula 1:

[0010] [ka]

[0011] In the above Chemical Formula 1, M is Ti, Zr, or Hf; R1 and R9 are represented by the following chemical formula 2: R2 to R8 and R 10 ~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; 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 each independently represent an alkyl group having 1 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms;

[0012] [ka]

[0013] In the above Chemical Formula 2, R 17 ~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; X is O, S, C(R 25 R 26 ), or N(R 27 ), where R 25 ~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 alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, R 17 ~R 24 Any one of the above is a position where it is connected to Chemical Formula 1.

[0014] (2) In the present invention, in the chemical formula 1, M is Hf, and R2 to R8 and R 10 ~R16 are each independently hydrogen, F, or an alkyl group having 1 to 10 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.

[0015] (3) In the present invention, in the above-mentioned chemical formula 2, R 17 ~R 24 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and 17 or R 20 is the position where it is connected to Chemical Formula 1, and X is O, S, C(R 25 R 26 ), or N(R 27 ), where R 25 ~R 27 and each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.

[0016] (4) In the present invention, there is provided the transition metal compound according to any one of (1) to (3), wherein the transition metal compound represented by Chemical Formula 1 is one selected from the group consisting of Chemical Formulas 1-1 to 1-4 below:

[0017] [ka]

[0018] [ka]

[0019] [ka]

[0020] [ka]

[0021] In the above Chemical Formulas 1-1 to 1-4, M is Ti, Zr, or Hf; 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, 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 each independently represent an alkyl group having 1 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms; X is O, S, C(R 25 R 26 ), or N(R 27 ), where R 25 ~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 alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms.

[0022] (5) In the present invention, there is provided the transition metal compound according to any one of (1) to (4) above, wherein the transition metal compound represented by Chemical Formula 1 is one selected from the group consisting of the following compounds:

[0023] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0024] (6) The present invention provides a catalyst composition comprising the transition metal compound according to any one of (1) to (5) above and a co-catalyst.

[0025] (7) In the present invention, there is provided the catalyst composition according to (6) above, wherein the co-catalyst comprises one or more selected from the following chemical formulas 3 to 5:

[0026] [Chemical formula 3] -[Al(R a )-O] m -

[0027] [Chemical formula 4] D(R a )3

[0028] [Chemical formula 5] [LH] + [Z(A)4] - or [L] + [Z(A)4] -

[0029] In the above formula, R aare each independently a halogen radical; a hydrocarbyl radical having 1 to 20 carbon atoms; or a hydrocarbyl radical having 1 to 20 carbon atoms substituted with a halogen; m is an integer of 2 or greater, D is aluminum or boron; L is a neutral or cationic Lewis acid; Z is a group 13 element, Each A is independently an aryl having 6 to 20 carbon atoms in which one or more hydrogen atoms may be substituted; or an alkyl having 1 to 20 carbon atoms, The substituent of A is a halogen; a hydrocarbyl having 1 to 20 carbon atoms; an alkoxy having 1 to 20 carbon atoms; or an aryloxy having 6 to 20 carbon atoms.

[0030] (8) The present invention provides a method for producing an olefin polymer, which comprises a step of polymerizing an olefin monomer in the presence of the catalyst composition according to (6) or (7) above.

[0031] (9) The present invention provides the method for producing an olefin polymer according to (8) above, wherein the olefin polymer is an ethylene / α-olefin copolymer. [Effects of the Invention]

[0032] By using the transition metal compound according to the present invention as a catalyst, an olefin polymer having a high melting temperature and a high molecular weight can be easily produced. DETAILED DESCRIPTION OF THE INVENTION

[0033] The present invention will now be described in more detail so that the present invention may be more easily understood. The terms and words used in the description of the present invention and the claims should not be interpreted in a limited way to their ordinary or dictionary meanings, but should be interpreted in a way that is consistent with the technical idea of ​​the present invention, based on the principle that the inventors can appropriately define the concepts of terms in order to best describe their inventions.

[0034] The term "alkyl," as used herein, unless otherwise specified, means a straight-chain, cyclic, or branched hydrocarbon residue, including, by way of non-limiting example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, and hexyl.

[0035] The term "cycloalkyl," as used herein, unless otherwise specified, refers to a non-aromatic cyclic hydrocarbon radical composed of carbon atoms. "Cycloalkyl" includes, by way of non-limiting example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.

[0036] As used herein, unless otherwise specified, the term "aryl" refers to an optionally substituted benzene ring or ring system that can be formed by condensing one or more optional substituents. Exemplary optional substituents are substituted C l-3 Alkyl, substituted C 2-3 Alkenyl, substituted C 2-3 "Aryl" groups include alkynyl, heteroaryl, heterocycle, aryl, alkoxy, aryloxy, aralkoxy, acyl, aroyl, heteroaroyl, acyloxy, aroyloxy, heteroaroyloxy, sulfanyl, sulfinyl, sulfonyl, aminosulfonyl, sulfonylamino, carboxamido, aminocarbonyl, carboxy, oxo, hydroxy, mercapto, amino, nitro, cyano, halogen, or ureido, optionally having one to three fluorine substituents. Such rings or ring systems may be optionally fused to an aryl ring (e.g., a benzene ring), carbocycle, or heterocyclic ring, optionally having one or more substituents. "Aryl" groups include, but are not limited to, phenyl, naphthyl, tetrahydronaphthyl, biphenyl, indanyl, anthracyl, phenanthryl, and substituted derivatives thereof.

[0037] In the present invention, the term "alkylaryl" refers to an aryl group substituted with the above alkyl group. In the present invention, the term "arylalkyl" refers to an alkyl group substituted with the above-mentioned aryl group.

[0038] In the present invention, unless otherwise specified, the term "hydrocarbyl" refers to a monovalent hydrocarbon group having 1 to 20 carbon atoms and consisting only of carbon and hydrogen, such as alkyl, aryl, alkenyl, alkynyl, cycloalkyl, alkylaryl, or arylalkyl, regardless of its structure.

[0039] In the present invention, "alkylene group" can mean a divalent aliphatic saturated hydrocarbon such as methylene, ethylene, propylene, and butylene.

[0040] In the present invention, the term "alkoxy group" may refer to any functional group, atomic group, or compound in which the hydrogen at the terminal of an alkyl group is replaced with an oxygen atom, such as methoxy, ethoxy, propoxy, and butoxy. The transition metal compound of the present invention is characterized by being represented by the following chemical formula 1.

[0041] [ka]

[0042] In the above Chemical Formula 1, M is Ti, Zr, or Hf; R1 and R9 are represented by the following chemical formula 2: R2 to R8 and R 10 ~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; 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 each independently represent an alkyl group having 1 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms;

[0043] [ka]

[0044] In the above Chemical Formula 2, R 17 ~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; X is O, S, C(R 25 R 26 ), or N(R 27 ), where R 25 ~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 alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, R 17 ~R 24 Any one of the above is a position where it is connected to Chemical Formula 1.

[0045] The transition metal compound of the present invention has a structure in which a fused ring of a specific structure is substituted at the ortho position of a bisphenolate, and has differences in steric hindrance and electron density compared to conventional compounds, and is advantageous in terms of the activity of the transition metal compound and copolymerizability with comonomers.

[0046] Due to the characteristics of these substituents, the transition metal compounds of the present invention can produce polymers with high density regions that are more active than conventional bisphenolate compounds, a unique feature that can be achieved by the novel structure of the compounds newly developed in the present invention.

[0047] Specifically, in the above Chemical Formula 1, M may be Hf. Specifically, in the above Chemical Formula 1, R2 to R8 and R 10 ~R 16may each independently be hydrogen, F, or 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.

[0048] Specifically, in the above Chemical Formula 1, Y may 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 a propylene group.

[0049] Specifically, in the above chemical formula 1, X1 and X2 may each independently be 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 3 carbon atoms, such as a methyl group.

[0050] Specifically, in the above Chemical Formula 2, the R 17 or R 20 may be at the position where it is linked to Chemical Formula 1. Specifically, in the above-mentioned Chemical Formula 2, R 17 ~R 24 may each independently represent hydrogen or an alkyl group having 1 to 10 carbon atoms, for example, hydrogen, except for the position where it is connected to Chemical Formula 1.

[0051] Specifically, in the above Chemical Formula 2, X is O, S, C(R 25 R 26 ), or N(R 27 ), where R 25 ~R 27 may each independently be an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and R 25 and R 26 may each independently be an alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 3 carbon atoms, for example, a methyl group; R 27 may be an aryl group having 6 to 10 carbon atoms, for example, a phenyl group.

[0052] Specifically, the transition metal compound represented by Chemical Formula 1 may be one transition metal compound selected from the group consisting of Chemical Formulas 1-1 to 1-4 below.

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] In the above Chemical Formulas 1-1 to 1-4, M is Ti, Zr, or Hf; 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, 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 each independently represent an alkyl group having 1 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms; X is O, S, C(R 25 R 26 ), or N(R 27 ), where R 25 ~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 alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms.

[0058] The transition metal compound represented by Chemical Formula 1 may be one selected from the group consisting of the following compounds, but is not limited thereto, and all transition metal compounds corresponding to Chemical Formula 1 are included in the present invention.

[0059] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0060] The catalyst composition of the present invention is characterized by comprising the transition metal compound represented by the above Chemical Formula 1 and a co-catalyst. For purposes of the present invention, the term "composition" includes mixtures of materials comprising the composition as well as reaction products and decomposition products formed from the materials of the composition.

[0061] The catalyst composition of the present invention may further contain a promoter. The co-catalyst may be one known in the art, and for example, one or more co-catalysts selected from the following chemical formulas 4 to 6 may be used.

[0062] [Chemical formula 4] -[Al(R a )-O] m -

[0063] [Chemical formula 5] D(R a )3

[0064] [Chemical formula 6] [LH] + [Z(A)4] - or [L] + [Z(A)4] -

[0065] In the above formula, R a are each independently a halogen radical; a hydrocarbyl radical having 1 to 20 carbon atoms; or a hydrocarbyl radical having 1 to 20 carbon atoms substituted with a halogen; m is an integer of 2 or greater, D is aluminum or boron; L is a neutral or cationic Lewis acid; Z is a group 13 element, Each A is independently an aryl group having 6 to 20 carbon atoms in which one or more hydrogen atoms may be substituted; or an alkyl group having 1 to 20 carbon atoms, The substituent of A is a halogen group; a hydrocarbyl 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.

[0066] The compound represented by Chemical Formula 4 is not particularly limited as long as it is an alkylaluminoxane. Preferred examples include methylaluminoxane, ethylaluminoxane, isobutylaluminoxane, and butylaluminoxane, and a particularly preferred compound is methylaluminoxane.

[0067] The compound represented by Chemical Formula 5 is not particularly limited, but preferred examples include trimethylaluminum, triethylaluminum, triisobutylaluminum, tripropylaluminum, tributylaluminum, dimethylchloroaluminum, tri-s-butylaluminum, tricyclopentylaluminum, tripentylaluminum, triisopentylaluminum, trihexylaluminum, trioctylaluminum, ethyldimethylaluminum, methyldiethylaluminum, triphenylaluminum, tri-p-tolylaluminum, dimethylaluminum methoxide, dimethylaluminum ethoxide, trimethylboron, triethylboron, triisobutylboron, tripropylboron, and tributylboron, and particularly preferred compounds are selected from trimethylaluminum, triethylaluminum, and triisobutylaluminum.

[0068] An example of the compound represented by Chemical Formula 6, when Z is boron, is dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate [(C 18 H 37 )2N(H)Me] + [B(C6F5)4] -, dioctadecylmethylammonium tetrakis(phenyl)borate, dioctadecylmethylammonium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, triethylammonium tetraphenylborate, tributylammonium tetraphenylborate, trimethylammonium tetraphenylborate, tripropylammonium tetraphenylborate, trimethylammonium tetra(p-tolyl)borate, trimethylammonium tetra(o,p-dimethylphenyl)borate, tributylammonium tetra(p-trifluoromethylphenyl)borate, trimethylammonium tetra(p-trifluoromethylphenyl)borate, tributylammonium tetrapentafluorophenylborate, N,N-diethylanilinium tetraphenylborate, N,N-diethylanilinium tetrapentafluorophenylborate, diethylammonium tetrapentafluorophenylborate, triphenylphosphonium tetraphenylborate, trimethylphosphonium tetraphenylborate, tripropylammonium tetra(p-tolyl)borate, tri Z may be ethylammonium tetra(o,p-dimethylphenyl)borate, trimethylammonium tetra(o,p-dimethylphenyl)borate, triphenylcarbonium tetra(p-trifluoromethylphenyl)borate, triphenylcarbonium tetrapentafluorophenylborate, or a combination thereof. When Z is aluminum, for example, triethylammonium tetraphenylaluminum, tributylammonium tetraphenylaluminum, trimethylammonium tetraphenylaluminum, tripropylammonium tetraphenylaluminum, trimethylammonium tetra(p-tolyl)aluminum, tripropylammonium tetra(p-tolyl)aluminum, triethylammonium tetra(o,p-dimethylphenyl)aluminum, tributylammonium tetra(p-trifluoromethylphenyl)aluminum, trimethylammonium tetra(p-trifluoromethylphenyl)aluminum, tributylammonium tetrapentafluorophenylaluminum, N,N-diethylanilinium tetraphenylaluminum, N,The compound may be, but is not limited to, N-diethylanilinium tetrapentafluorophenylaluminum, diethylammonium tetrapentatetraphenylaluminum, triphenylphosphonium tetraphenylaluminum, trimethylphosphonium tetraphenylaluminum, triethylammonium tetraphenylaluminum, tributylammonium tetraphenylaluminum, or a combination thereof.

[0069] In particular, the co-catalyst used in the present invention may be a compound represented by the above Chemical Formula 6, specifically, dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate.

[0070] In addition, the transition metal compound represented by Chemical Formula 1 and the co-catalyst may be used in a form supported on a carrier. The carrier may be, but is not limited to, silica or alumina.

[0071] The method for producing an olefin polymer of the present invention is characterized by comprising a step of polymerizing an olefin monomer in the presence of the catalyst composition. In the present invention, the term "polymer" refers to a polymeric compound prepared by polymerizing the same or different types of monomers. Thus, the general term "polymer" encompasses the term "homopolymer," which is commonly used to refer to a polymer prepared from only one type of monomer, and the term "interpolymer," as defined below.

[0072] In the present invention, the term "interpolymer" refers to a polymer prepared by polymerization of at least two different monomers. Thus, the general term "interpolymer" includes copolymers, which are commonly used to refer to polymers prepared from two different monomers, and polymers prepared from two or more different monomers.

[0073] In the present invention, the olefin monomer may be at least one 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, but is not limited thereto.

[0074] Specifically, the olefin polymer of the present invention may be an olefin homopolymer or an olefin / α-olefin copolymer, preferably an ethylene / α-olefin copolymer, depending on the type of olefin monomer. In this case, the content of the α-olefin monomer as a comonomer may be appropriately selected by a skilled artisan depending on the application and purpose of the olefin polymer, and may be about 1 to 99 mol%.

[0075] The catalyst composition can be dissolved or diluted in an aliphatic hydrocarbon solvent having 5 to 12 carbon atoms suitable for the polymerization process of olefin monomers, such as pentane, hexane, heptane, nonane, decane, and isomers thereof, aromatic hydrocarbon solvents such as toluene and benzene, and chlorine-substituted hydrocarbon solvents such as dichloromethane and chlorobenzene, and can be injected. The solvent used here is preferably treated with a small amount of alkylaluminum to remove small amounts of water or air, which act as catalyst poisons, and a cocatalyst can also be used.

[0076] The most preferred manufacturing process using the catalyst compositions is a solution process, although when such compositions are used with an inorganic support such as silica, slurry or gas phase processes are also possible.

[0077] The polymerization may be carried out using a single continuous slurry polymerization reactor, a loop slurry reactor, a gas phase reactor, or a solution reactor to homopolymerize one olefin monomer or to copolymerize two or more olefin monomers.

[0078] During the polymerization reaction, an organoaluminum compound may be added to remove moisture from the reactor, and the polymerization reaction may be carried out in the presence of the compound. Specific examples of such organoaluminum compounds include trialkylaluminum, dialkylaluminum halides, alkylaluminum dihalides, aluminum dialkyl hydrides, and alkylaluminum sesquihalides. More specific examples include Al(C2H5)3, Al(C2H5)2H, Al(C3H7)3, Al(C3H7)2H, Al(i-C4H9)2H, and 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, (C2H5)2AlCl, (i-C3H9)2AlCl, or (C2H5)3Al2Cl3. Such organoaluminum compounds may be continuously added to the reactor, and may be added at a rate of about 0.1 to 10 moles per kg of reaction medium added to the reactor to allow for adequate moisture removal.

[0079] According to one embodiment of the present invention, the polymerization of the olefin polymer may be carried out at a temperature of about 80 to 200°C, specifically about 90 to 200°C, or about 130 to 200°C, and a pressure of about 20 to 100 bar, specifically about 20 to 50 bar, or about 20 to 40 bar, for about 8 minutes to 2 hours.

[0080] Example The present invention will be described in more detail below with reference to examples. However, the following examples are for illustrative purposes only and the scope of the present invention is not limited to these examples.

[0081] <Production of transition metal compounds> Manufacturing Example 1 [ka]

[0082] The compound was prepared according to the following reaction scheme: [ka]

[0083] (1) Preparation of Compound 1-1 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 added and the mixture was warmed to room temperature. After stirring at room temperature for 30 minutes, the mixture was cooled to 0°C again and chloro(methoxy)methane (5.80 g, 72 mmol) was added. The mixture was warmed to room temperature and stirred for 3 hours. Upon completion of the reaction, 500 mL of water was added and the mixture was extracted with ethyl acetate. The separated organic layer was washed twice with 300 mL of water, separated, slurried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to produce compound 1-1 as an oil (17 g, 95% yield).

[0084] (2) Preparation of Compound 1-2 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, and then 30 mL of aqueous potassium carbonate (10.6 g, 77 mmol) was added and heated. Tetrakis-(triphenylphosphine)palladium (0.15 g, 0.13 mmol) was added to the refluxing mixture and stirred at reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the tetrahydrofuran was removed by concentration under reduced pressure. Ethyl acetate was added to the mixture and dissolved, then washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The mixture was slurried with a small amount of tert-butyl methyl ether and excess hexane, stirred at room temperature for 2 hours, and filtered to produce the dark gray target compound 1-2 (9.0 g, 97% yield).

[0085] (3) Preparation of Compound 1-3 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 added. The temperature was raised to room temperature and stirred for 2 hours, after which triisopropyl borate (4.7 mL, 20.2 mmol) was added. After stirring at room temperature for approximately 1 hour, the reaction was completed. 50 mL of 1N aqueous HCl solution was added and stirred. The organic layer was extracted with ethyl acetate and separated. The organic layer was washed once with water, separated, treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. Target compound 1-3 was produced as a mixture of yellow foam and oil (6.3 g, 84.7% yield).

[0086] (4) Preparation of Compound 1-4 The 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, and then potassium carbonate (21.7 g, 157 mmol) was added and heated. After stirring at reflux for 12 hours, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure, and the concentrated compound was redissolved in ethyl acetate and washed twice with water. The organic layer was separated, slurried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was slurried in a small amount of hexane and filtered to obtain white solid compound 1-4 (8.3 g, 75.1% yield).

[0087] (5) Preparation of Compound 1-5 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 then 20 mL of aqueous potassium carbonate (3.9 g, 28.4 mmol) was added. The mixture was heated to reflux, and tetrakis-(triphenylphosphine)palladium (0.16 g, 0.14 mmol) was added and stirred at reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature, and ethyl acetate was added. The mixture was washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified by silica column chromatography to produce the target compound 1-5 as a white solid (2.0 g, 28.7% yield).

[0088] (6) Preparation of Compounds 1-6 Compound 1-5 (2.0 g, 2.04 mmol) was added to methanol and stirred. 0.5 mL of concentrated hydrochloric acid was added and the mixture was heated. After stirring under reflux for 12 hours or more, the mixture was cooled to room temperature and then diluted with saturated aqueous sodium bicarbonate. P After reducing to H7-8, it was extracted with ethyl acetate. The extracted organic layer was washed once with water, slurried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The target compound 1-6 was purified and separated by column chromatography using a 5 / 1 mixture of hexane and ethyl acetate (1.13 g, 62% yield).

[0089] (7) Preparation of Compound 1 In a glovebox, 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 slowly added with 3.0 M methylmagnesium bromide solution (1.5 mL, 4.5 mmol) at room temperature. After stirring for 12 hours, 10 mL of hexane was added to the mixture, which was stirred for approximately 3 hours and then filtered through a Celite pad. The filtrate was concentrated under reduced pressure, and 20 mL of a 1:1 solution of toluene and hexane was added to the concentrated compound. The mixture was slurried for 3 hours and then filtered. The filtrate was concentrated under reduced pressure to produce compound 1 (0.9 g, 73% yield) as a white solid.

[0090] 1H NMR (500MHz, 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)

[0091] Manufacturing Example 2 [ka]

[0092] The compound was prepared according to the following reaction scheme: [ka]

[0093] (1) Preparation of Compound 2-1 Using 2-bromo-4-methylphenol (5.0 g, 26.7 mmol), an experiment was carried out in the same manner as in the preparation example of compound 1-1 to prepare the target compound 2-1 (6.1 g, yield 98.7%).

[0094] (2) Preparation of Compound 2-2 Compound 2-1 (10 g, 43.3 mmol) and (9,9-dimethyl-9H-fluoren-4-yl)boronic acid (10.8 g, 45.4 mmol) were used in the same manner as in the preparation example of compound 1-2, and the target compound 2-2 was produced as a yellow oil (14.5 g, yield 97.3%).

[0095] (3) Preparation of Compound 2-3 Compound 2-3 was synthesized using compound 2-2 (15.5 g, 48.8 mmol) in the same manner as in the preparation example of compound 1-3. The compound was purified by column chromatography using a 10 / 1 mixed solvent of hexane and ethyl acetate to produce a white solid compound 2-3 (9.6 g, yield 50.6%).

[0096] (4) Preparation of Compound 2-4 Compound 2-4 was synthesized using compound 2-3 (4.6 g, 11.9 mmol) and compound 1-4 (2.0 g, 4.7 mmol) in the same manner as in the preparation example for compound 1-5. The compound was purified by column chromatography using a 20 / 1 mixed solvent of hexane and ethyl acetate to produce a white solid compound 2-4 (3.02 g, yield 66.7%).

[0097] (5) Preparation of Compound 2-5 Compound 2-4 (3.0 g, 3.16 mmol) was used in the same experiment as in the preparation example of compound 1-6 to prepare the pale yellow target compound 2-5 (1.1 g, yield 36.7%).

[0098] (6) Preparation of Compound 2 In a glovebox, 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 slowly added with 3.0 M methylmagnesium bromide solution (1.8 mL, 5.4 mmol) at room temperature. After stirring for 12 hours, 10 mL of hexane was added to the mixture, which was stirred for approximately 3 hours and then filtered through a Celite pad. The filtrate was concentrated under reduced pressure, and 20 mL of a 1:1 solution of toluene and hexane was added to the concentrated compound. The mixture was slurried for 3 hours and then filtered. The filtrate was concentrated under reduced pressure to produce compound 2 as a white solid (1.35 g, 91% yield).

[0099] 1 H NMR (500MHz, 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)

[0100] Manufacturing Example 3 [ka]

[0101] The compound was prepared according to the following reaction scheme: [ka]

[0102] (1) Preparation of Compound 3-1 Compound 2-1 (5 g, 21.6 mmol) and (9-phenyl-9H-carbazol-1-yl)boronic acid (6.5 g, 22.7 mmol) were used in the same manner as in the preparation of compound 1-2 to produce the target compound 3-1 as a white solid (6.21 g, 73% yield).

[0103] (2) Preparation of Compound 3-2 Using compound 3-1 (3.5 g, 8.9 mmol), an experiment was carried out in the same manner as in the preparation example of compound 1-3 to prepare a white solid compound 3-2 (2.52 g, yield 65%).

[0104] (3) Preparation of Compound 3-3 Using 2-bromo-4-methylphenol (6.0 g, 32.1 mmol), the same experiment as in the preparation example of compound 1-4 was carried out to prepare a white solid compound 3-3 (5.84 g, 88% yield).

[0105] (4) Preparation of Compound 3-4 Using compound 3-2 (5.0 g, 11.4 mmol) and compound 3-3 (2.13 g, 5.15 mmol), an experiment similar to the preparation example of compound 1-5 was carried out to prepare the pale gray target compound 3-4 (4.01 g, 75% yield).

[0106] (5) Preparation of Compound 3-5 Compound 3-4 (5.0 g, 4.81 mmol) was used in the same experiment as in the preparation example of compound 1-6 to prepare the white target compound 3-5 (3.52 g, 77% yield).

[0107] (6) Preparation of Compound 3 An experiment was carried out in a glove box using compound 3-5 (1.10 g, 1.16 mmol) in the same manner as in the preparation example of compound 1 to produce white target compound 3 (0.45 g, yield 49%).

[0108] 1 H NMR (500MHz, 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)

[0109] Production Example 4 [ka]

[0110] The compound was prepared according to the following reaction scheme: [ka]

[0111] (1) Preparation of Compound 4-1 Compound 2-1 (5.0 g, 21.6 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (5.18 g, 22.7 mmol) were used in the same manner as in the preparation example for compound 1-2 to produce the target compound 4-1 (5.28 g, 73% yield).

[0112] (2) Preparation of Compound 4-2 Compound 4-1 (5.0 g, 15.0 mmol) was used in the same experiment as in the preparation example of compound 1-3 to prepare the target compound 4-2 (3.84 g, yield 68%).

[0113] (3) Preparation of Compound 4-3 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 added and stirred at the same temperature for 1 hour. The reaction mixture was then poured into 500 mL of water. The organic layer was extracted with dichloromethane and washed once with 500 mL of water. The separated organic layer was slurried with anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The oily concentrate was slurried with ethyl acetate and hexane and filtered to produce the target compound 4-3 as a white solid (11.2 g, 81% yield).

[0114] (4) Preparation of Compound 4-4 Using compound 4-3 (8.0 g, 28.1 mmol) and 1,3-dibromopropane (2.83 g, 14.0 mmol), an experiment similar to that in the preparation example of compound 1-4 was carried out to prepare the target compound 4-4 (6.5 g, yield 76%).

[0115] (5) Preparation of Compound 4-5 Using compound 4-2 (5.3 g, 14.0 mmol) and compound 4-4 (4.3 g, 7.1 mmol), an experiment similar to that in the preparation example of compound 1-5 was carried out to prepare the target compound 4-5 as a white solid (6.0 g, yield 77%).

[0116] (6) Preparation of Compound 4-6 Compound 4-5 (4.5 g, 4.0 mmol) was used in the same experiment as in the preparation example of compound 1-6 to prepare the target compound 4-6 (3.8 g, yield 91%).

[0117] (7) Preparation of Compound 4 An experiment was carried out in a glove box using compound 4-6 (0.78 g, 0.76 mmol) in the same manner as in the preparation example of compound 1 to produce the target compound 4 as a white solid (0.61 g, yield 65%).

[0118] 1H NMR (500MHz, CDCl3): 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)

[0119] Comparative Manufacturing Example 1 [ka]

[0120] The compound was prepared according to the following reaction scheme: [ka]

[0121] (1) Preparation of Compound C1-2 Compound C1-1 (5.0 g, 13.1 mmol) was used in the same experiment as in the preparation example of compound 1-3 to prepare the target compound C1-2 (5.4 g, yield 97%).

[0122] (2) Preparation of Compound C1-3 Using compound C1-2 (4.42 g, 10.4 mmol) and compound 4-4 (2.0 g, 4.7 mmol), an experiment similar to that in the preparation example of compound 1-5 was carried out to prepare the target compound 4-5 as a white solid (1.2 g, yield 24.8%).

[0123] (3) Preparation of Compound C1-4 Compound C1-3 (5.6 g, 4.7 mmol) was dissolved in 15 mL of a 1 / 1 mixture of methanol and tetrahydrofuran, followed by the addition of p-toluenesulfonic acid (2.0 g, 4.7 mmol) at room temperature and heating to 50°C. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove the solvent. The solution was then diluted again with ethyl acetate and washed twice with water. The organic layer was separated, slurried with anhydrous magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure. The concentrated compound was purified by column chromatography using a 2 / 1 mixture of hexane and ethyl acetate to produce the target compound C1-4 as a white solid (1.2 g, 30% yield).

[0124] (4) Preparation of Compound C1 Using compound C1-4 (1.0 g, 1.2 mmol), an experiment was carried out in the same manner as in the preparation example of compound 1 to prepare the target compound C1 as a white solid (0.3 g, yield 24.1%).

[0125] Comparative Manufacturing Example 2 [ka]

[0126] The compound was prepared according to the following reaction scheme: [ka]

[0127] (1) Preparation of Compound C2-1 Compound 2-1 (5.0 g, 21.6 mmol) and carbazole (3.12 g, 22.7 mmol) were dissolved in 50 mL of toluene, followed by the addition of 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). The mixture was heated and refluxed under stirring. After the reaction was complete, the solution was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The resulting mixture was slurried in a 4:1 mixture of hexane and ethyl acetate to produce the pale red target compound C2-1 (4.7 g, 68% yield).

[0128] (2) Preparation of Compound C2-2 Compound C2-1 (18.7 g, 58.9 mmol) was used in the same experiment as in the preparation example of compound 1-3 to prepare the target compound C2-2 (21 g, yield 99%).

[0129] (3) Preparation of Compound C2-3 Using compound C2-2 (7.53 g, 20.9 mmol) and compound 4-4 (4.0 g, 9.5 mmol), the same experiment as in Preparation Example 1-5 was carried out to produce the target compound C2-3 (7.0 g, 82% yield).

[0130] (4) Preparation of Compound C2-4 Compound C2-3 (1.0 g, 1.1 mmol) was used in the same experiment as in the preparation example of compound 1-6 to prepare the target compound C2-4 as a white solid (0.8 g, yield 88.7%).

[0131] (5) Preparation of Compound C2 Using compound C2-4 (1.0 g, 1.2 mmol), an experiment was carried out in the same manner as in the preparation example of compound 1 to prepare the target compound C2 as a white solid (0.9 g, yield 71.6%).

[0132] <Polymerization of ethylene / α-olefin copolymer> Example 1 A 2L autoclave reactor was charged with hexane solvent (900mL) and 1-octene (300mL), and then preheated to 150°C. Simultaneously, the reactor was pre-charged with ethylene (35bar). 3µmol of the catalyst from Preparation Example 1, 30µmol of dimethylanilinium tetrakis(pentafluorophenyl)borate cocatalyst (AB) (10eq relative to the catalyst), and 0.6mmol of Tibal as a scavenger were sequentially charged into the reactor under high-pressure argon pressure, and the copolymerization reaction was carried out for 8 minutes. The remaining ethylene gas was then vented, and the polymer solution was added to excess ethanol to induce precipitation. The precipitated polymer was washed two to three times with ethanol and then dried in a vacuum oven at 90°C for at least 12 hours.

[0133] Examples 2 to 4, Comparative Examples 1 and 2 Ethylene / α-olefin copolymers were produced in the same manner as in Example 1, except that the type of catalyst was changed according to Table 1 below.

[0134] [Table 1]

[0135] <Analysis of Ethylene / α-Olefin Copolymer Production Results> Experimental Example 1 The physical properties of the copolymers prepared in the above examples and comparative examples were compared and analyzed. The measurement conditions and methods are as follows.

[0136] (1) Catalytic activity (kgPE / mmol) The obtained polymer was dried in vacuum to measure the yield, and the value was calculated by dividing the polymer (kg) by the catalyst (mmol).

[0137] (2) Density Measurement was carried out in accordance with ASTM D-792.

[0138] (3) Melting Temperature (Tm) The melting temperature (Tm) can be measured using a PerkinElmer Differential Scanning Calorimeter (DSC6000). Specifically, the copolymer was heated to 150°C under a nitrogen atmosphere, maintained at this temperature for 5 minutes, then cooled to -100°C, and the DSC curve was observed while the temperature was increased again. The heating and cooling rates were both 10°C / min. In the measured DSC curve, the melting temperature was determined as the maximum point of the endothermic peak during the second heating.

[0139] [Table 2]

[0140] As shown in the results in Table 2, by using the transition metal compound of Chemical Formula 1 as a catalyst, it is possible to produce a polymer in the high density region with superior catalytic activity compared to the conventional compound of Comparative Example 1, and it is possible to produce a polymer in the high density region compared to the compound of Comparative Example 2. This indicates that it is possible to produce high density polyolefins with high productivity by using the transition metal compound of Chemical Formula 1 developed in the present invention as a catalyst.

Claims

1. A transition metal compound represented by the following chemical formula 1. 【Chemistry 1】 In the above Chemical Formula 1, M is Ti, Zr, or Hf; R １ and R ９ is represented by the following chemical formula 2: R ２ ~R ８ and R １０ ~R １６ are each independently hydrogen, F, Cl, CN, or CF ３ , 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; 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; X １ and X ２ are each independently an alkyl group having 1 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms, 【Chemistry 2】 In the above Chemical Formula 2, R １７ ~R ２４ are each independently hydrogen, F, Cl, CN, or CF ３ , 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; X is O, S, C (R ２５ R ２６ ), or N(R ２７ ), where R ２５ ~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 alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms, The R １７ ~R ２４ is a position where it is connected to Chemical Formula 1.

2. In the above Chemical Formula 1, M is Hf; R ２ ~R ８ and R １０ ~R １６ are each independently hydrogen, F, or an alkyl group having 1 to 10 carbon atoms; Y is an alkylene group having 1 to 10 carbon atoms; X １ and X ２ and each independently represent an alkyl group having 1 to 10 carbon atoms.

3. In the above Chemical Formula 2, R １７ ~R ２４ are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, The R １７ or R ２０ is the position at which the compound is linked to Chemical Formula 1; X is O, S, C (R ２５ R ２６ ), or N(R ２７ ), where R ２５ ~R ２７ and each independently represent 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 Chemical Formula 1 is one selected from the group consisting of Chemical Formulas 1-1 to 1-4 below. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 In the chemical formulas 1-1 to 1-4, M is Ti, Zr, or Hf; R ３ , R ６ , R １１ , and R １４ are each independently F, Cl, CN, or CF ３ , 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; 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; X １ and X ２ are each independently an alkyl group having 1 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms, X is O, S, C (R ２５ R ２６ ), or N(R ２７ ), where R ２５ ~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 alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms.

5. 2. The transition metal compound according to claim 1, wherein the transition metal compound represented by Chemical Formula 1 is one selected from the group consisting of the following compounds: 【Chemical 7A】 【Chemistry 7B】 【Chem.7C】 【7D Transformation】 [Transformation 7E] 【Chemical 7F】 【7G】 【Chemical 7H】 【Chemical Formula 7I】 【Chemical 7J】 [7K] [7L]

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

7. The catalyst composition according to claim 6, wherein the co-catalyst comprises one or more selected from the following Formulas 3 to 5: [Chemical formula 3] -[Al(R ａ )-O] ｍ - [Chemical formula 4] D(R ａ ) ３ [Chemical formula 5] [L-H] ＋ [Z(A) ４ ] － or [L] ＋ [Z(A) ４ ] － In the above formula, R ａ are each independently a halogen radical; a hydrocarbyl radical having 1 to 20 carbon atoms; or a hydrocarbyl radical having 1 to 20 carbon atoms substituted with a halogen; m is an integer of 2 or greater; D is aluminum or boron; L is a neutral or cationic Lewis acid; Z is a Group 13 element; Each A is independently an aryl having 6 to 20 carbon atoms in which one or more hydrogen atoms may be substituted; or an alkyl having 1 to 20 carbon atoms, The substituent of A is halogen; hydrocarbyl having 1 to 20 carbon atoms; alkoxy having 1 to 20 carbon atoms; or aryloxy having 6 to 20 carbon atoms.

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

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

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