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. 10-2023-0022825, filed February 21, 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 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, Ring A is [ka] or [ka] wherein R2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and when R2 is substituted, it is substituted with an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms; m is 1 and n is 3, or m is 2 and n is 2; X's 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.

[0012] (2) The present invention provides the transition metal compound according to (1) above, wherein M is Hf, R1 is an alkyl group having 1 to 15 carbon atoms, R2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and when R2 is substituted, it is substituted with an alkyl group having 1 to 15 carbon atoms, m is 1, and n is 3.

[0013] (3) The present invention provides a transition metal compound according to (1) or (2) above, wherein M is Hf, R1 is an alkyl group having 1 to 15 carbon atoms, R2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and when R2 is substituted, it is substituted with an alkyl group having 1 to 15 carbon atoms, m is 2, and n is 2.

[0014] (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:

[0015] [ka]

[0016] [ka]

[0017] [ka]

[0018] [ka]

[0019] In the above Chemical Formulas 1-1 to 1-4, R1 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, R2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and when R2 is substituted, it is substituted with an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms; X's 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.

[0020] (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:

[0021] [ka] [ka] [ka] [ka]

[0022] (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.

[0023] (7) In the present invention, there is provided the catalyst composition according to (6) above, which further comprises a transition metal compound represented by the following chemical formula 2:

[0024] [ka]

[0025] In the above Chemical Formula 2, Q is Ti, Zr, or Hf; R 13 ~R 16 are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and two or more adjacent groups thereof may be linked to form a ring; R 17 and R 18 are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution is with an alkyl group having 1 to 6 carbon atoms; R 19 are each independently an alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, n is 1 to 5; Y1 and Y2 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.

[0026] (8) In the present invention, there is provided the catalyst composition according to (6) or (7) above, wherein the transition metal compound represented by Chemical Formula 2 is a compound represented by Chemical Formula 2A below:

[0027] [ka]

[0028] In the chemical formula 2A, Q is Ti, Zr, or Hf; R 17 and R 18 are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution is with an alkyl group having 1 to 6 carbon atoms; R 19 are each independently an alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, Y1 and Y2 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.

[0029] (9) In the present invention, there is provided the catalyst composition according to any one of (6) to (8) above, wherein the co-catalyst includes one or more selected from the following Chemical Formulas 3 to 5:

[0030] [Chemical formula 3] -[Al(R a )-O] m -

[0031] [Chemical formula 4] D(R a)3

[0032] [Chemical formula 5] [LH] + [Z(A)4] - or [L] + [Z(A)4] -

[0033] 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.

[0034] (10) The present invention provides a method for producing an olefin polymer, comprising a step of polymerizing an olefin monomer in the presence of the catalyst composition according to any one of (6) to (9) above.

[0035] (11) The present invention provides the method for producing an olefin polymer according to (10) above, wherein the olefin polymer is an ethylene / α-olefin copolymer. [Effects of the Invention]

[0036] 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

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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. The transition metal compound of the present invention is characterized by being represented by the following chemical formula 1.

[0043] [ka]

[0044] In the above Chemical Formula 1, M is Ti, Zr, or Hf; R1 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, Ring A is [ka] or [ka] wherein R2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and when R2 is substituted, it is substituted with an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms; m is 1 and n is 3, or m is 2 and n is 2; X's 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.

[0045] The transition metal compound of the present invention is a fused-ring pyrimidine derivative containing a highly electron-dense sulfur (S) atom, and is substituted with secondary amines at the 2- and 4-positions. Depending on the substitution positions, a square ring is formed between the nitrogen atom at the 1- or 3-position of the pyrimidine and the transition metal. This structural uniqueness allows for the formation of a copolymer that has low copolymerizability with comonomers compared to monomers and has high crystallinity.

[0046] Thus, the transition metal compound of the present invention can be usefully used as a catalyst for producing olefin polymers, and this is a unique feature that can be achieved by the novel structure of the compound newly developed in the present invention.

[0047] Specifically, in the above Chemical Formula 1, M may be Hf. Specifically, in Chemical Formula 1, R1 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, and may be an alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 6 carbon atoms, specifically a propyl group.

[0048] Specifically, in the above Chemical Formula 1, ring A is [ka] or [ka] wherein R2 may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and when R2 is substituted, it may be substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, or an alkyl group having 1 to 15 carbon atoms. Specifically, in Chemical Formula 1, R2 may be a phenyl group, a naphthalene group, or the like, and R2 may be substituted with an alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 6 carbon atoms, for example, a methyl group, and the number of substituents may be multiple.

[0049] Specifically, in the above Chemical Formula 1, m may be 1 and n may be 3, or m may be 2 and n may be 2. Specifically, in Chemical Formula 1, each X may independently represent an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 3 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or an arylalkyl group having 11 to 20 carbon atoms, specifically a methyl group, a phenyl group, or a phenylmethyl group (benzyl group).

[0050] 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.

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] In the above Chemical Formulas 1-1 to 1-4, R1 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, R2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and when R2 is substituted, it is substituted with an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms; X's 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.

[0056] 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.

[0057] [ka] [ka] [ka] [ka]

[0058] 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.

[0059] 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.

[0060] [Chemical formula 4] -[Al(R a )-O] m -

[0061] [Chemical formula 5] D(R a )3

[0062] [Chemical formula 6] [LH] + [Z(A)4] - or [L] + [Z(A)4] -

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] In the present invention, the catalyst composition may further include a transition metal compound represented by the following Chemical Formula 2:

[0070] [ka]

[0071] In the above Chemical Formula 2, Q is Ti, Zr, or Hf; R 13 ~R 16 are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and two or more adjacent groups thereof may be linked to form a ring; R 17 and R 18 are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution is with an alkyl group having 1 to 6 carbon atoms; R 19are each independently an alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, n is 1 to 5; Y1 and Y2 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.

[0072] In the present invention, when the transition metal compound represented by Chemical Formula 1 and the transition metal compound represented by Chemical Formula 2 are used together, a catalyst having high elasticity and a catalyst having excellent heat resistance are used in combination, so that a polymer having excellent elasticity and heat resistance can be produced.

[0073] Specifically, in the above Chemical Formula 2, Q may be Hf. Specifically, in the above-mentioned Chemical Formula 2, R 13 ~R 16 are each independently hydrogen or an alkyl group having 1 to 20 carbon atoms, and two or more adjacent groups thereof may be linked to each other to form a ring, or R 13 and R 14 are each independently an alkyl group having 1 to 20 carbon atoms, and are linked together to form an aromatic ring having 5 to 20 carbon atoms; 15 and R 16 may be hydrogen.

[0074] Specifically, in the above-mentioned Chemical Formula 2, R 17 and R 18 are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution may be with an alkyl group having 1 to 6 carbon atoms.

[0075] Specifically, in the above-mentioned Chemical Formula 2, R 19 may each independently be an alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, specifically an alkyl group having 3 to 6 carbon atoms. Specifically, in the above chemical formula 2, n may be 1 to 5, 1 to 3, specifically 2.

[0076] Specifically, in Chemical Formula 2, Y1 and Y2 may each independently be 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, or an alkylaryl group having 7 to 20 carbon atoms, specifically an alkyl group having 1 to 20 carbon atoms.

[0077] More specifically, the transition metal compound represented by Chemical Formula 2 may be a compound represented by Chemical Formula 2A below.

[0078] [ka]

[0079] In the chemical formula 2A, Q is Ti, Zr, or Hf; R 17 and R 18 are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution is with an alkyl group having 1 to 6 carbon atoms; R 19 are each independently an alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, Y1 and Y2 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. In the chemical formula 2A, Q, R 17 ~R 19 , Y1, and Y2 are as defined above.

[0080] The transition metal compound represented by Chemical Formula 2 may specifically be the following compound, but is not limited thereto, and all transition metal compounds corresponding to Chemical Formula 2 are included in the present invention.

[0081] [ka]

[0082] In addition, the transition metal compound represented by Chemical Formula 1 and the transition metal compound represented by Chemical Formula 2 in the catalyst composition may be in a ratio of 10:1 to 1:10, specifically 1:1 to 1:6, 1:1 to 1:5, or 1:3 to 1:4.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] 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%.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] <Production of transition metal compounds> Manufacturing Example 1 [ka]

[0094] The compounds were prepared according to the following method. [ka]

[0095] (1) Preparation of Compound S1-1 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (3.0 g, 11.8 mmol) and propan-1-amine (2.09 g, 35.3 mmol) were added to 30 mL of 1,4-dioxane. K2CO3 (4.9 g, 35.3 mmol) was added and the mixture was heated to 80 °C. After heating and stirring for approximately 12 hours, the mixture was cooled to room temperature and 100 mL of water was added. The precipitated solid was filtered, dissolved again in chloroform, washed once with water, separated, slurried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. A small amount of ethyl acetate was added to the concentrated compound and stirred at room temperature. The resulting solid was filtered to produce the white target compound S1-1 (2.7 g, yield 82.7%).

[0096] (2) Preparation of Compound S1-2 Compound S1-1 (2.0 g, 7.2 mmol) and mesitylboronic acid (1.3 g, 7.9 mmol) were dissolved in 60 mL of 1,4-dioxane, followed by the addition of 20 mL of K3PO4 (3.06 g, 14.4 mmol) in water and heating. Tricyclohexylphosphine (0.12 g, 0.4 mmol) and bis(dibenzylideneacetone)palladium(0) (0.12 g, 0.2 mmol) dissolved in 1,4-dioxane were added to the refluxing mixture and stirred for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature, the 1,4-dioxane was removed under reduced pressure, and the concentrated mixture was extracted with ethyl acetate. The organic layer was separated, washed once with water, slurried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The mixture was purified by column chromatography using a 50 / 1 mixture of hexane and ethyl acetate to produce the pale yellow target compound S1-2 (0.75 g, 29% yield).

[0097] (3) Preparation of Compound S1 In a glove box, compound S1-2 (0.1 g, 0.3 mmol) was dissolved in 10 mL of toluene, followed by the addition of n-BuLi (2.5 M in hexane) (0.12 mL, 0.3 mmol) and stirring at room temperature for 1 hour. In another flask, hafnium tetrachloride (0.09 g, 0.3 mmol) was diluted in 5 mL of toluene, followed by the addition of methylmagnesium bromide (3.0 M in diethyl ether) (0.41 mL, 1.2 mmol) at low temperature. After stirring for approximately 5 minutes, the compound S1-2 and n-BuLi mixture was added. The mixture was stirred at room temperature for 4 hours. 15 mL of hexane was added to the mixture and stirred for 2 hours. The mixture was filtered, and the filtrate was concentrated under reduced pressure. 5 mL of methyl tert-butyl ether was added and dissolved, and then the mixture was concentrated to about half its original volume and recrystallized to produce the target compound S1 (0.08 g, yield 49.5%).

[0098] 1 H NMR (500MHz, CDCl3): 8.40(d, 1H), 7.95(d, 1H), 7.63(t, 1H), 7.50(t, 1H), 6.83(s, 2H) ), 2.99(t, 2H), 2.36(s, 3H), 1.83(s, 6H), 1.59~1.64(q, 2H), 0.97(t, 3H), 0.20(s, 9H)

[0099] Manufacturing Example 2 [ka]

[0100] The compounds were prepared according to the following method. In a glove box, compound S1-2 (0.1 g, 0.3 mmol) was dissolved in 10 mL of toluene, followed by the addition of n-BuLi (2.5 M in hexane) (0.12 mL, 0.3 mmol) and stirring at room temperature for 1 hour. In another flask, hafnium tetrachloride (0.04 g, 0.15 mmol) was diluted in 5 mL of toluene, followed by the addition of methylmagnesium bromide (3.0 M in diethyl ether) (0.21 mL, 0.6 mmol) at low temperature. After stirring for approximately 5 minutes, the compound S1-2 and n-BuLi mixture was added. The mixture was stirred at room temperature for 4 hours. 5 mL of hexane was added to the mixture and stirred for 2 hours. The mixture was filtered through a celite pad, and the filtrate was concentrated under reduced pressure to prepare the target compound S2 (0.05 g, yield 38.9%).

[0101] 1 H NMR (500MHz, CDCl3): 8.41 (d, 2H), 7.96 (d, 2H), 7.63 (t, 2H), 7.49 (t, 2H), 6.84 (s, 4) H), 3.00(br, 4H), 2.36(s, 6H), 1.83(s, 12H), 1.61(m, 4H), 0.99(t, 6H), 0.20(s, 6H)

[0102] Manufacturing Example 3 [ka]

[0103] The compounds were prepared according to the following method. [ka]

[0104] (1) Preparation of Compound S3-1 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (3.0 g, 11.8 mmol) and mesitylboronic acid (2.12 g, 12.9 mmol) were dissolved in 40 mL of 1,4-dioxane, followed by the addition of 15 mL of aqueous K2CO3 (4.88 g, 35.3 mmol). Tetrakis(triphenylphosphine)-palladium(0) (0.14 g, 0.11 mmol) was added to the refluxing mixture and stirred at reflux for 12 h. Once the reaction was complete, the mixture was cooled to room temperature, the 1,4-dioxane was removed under reduced pressure, and the concentrated mixture was extracted with ethyl acetate. The organic layer was separated, washed once with water, slurried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The mixture was slurried in a mixture of excess hexane and a small amount of ethyl acetate to produce the pale yellow target compound S3-1 (3.5 g, 87.8% yield).

[0105] (2) Preparation of Compound S3-2 Compound S3-1 (3.0 g, 11.8 mmol) and 2-methylpropan-1-amine (0.44 mL, 4.4 mmol) were dissolved in 10 mL of N,N-dimethylformamide, followed by the addition of potassium iodide (0.05 g, 0.3 mmol) and triethylamine (1.23 mL, 8.9 mmol) and the mixture was heated to 60 °C. After stirring for 12 hours, the reaction mixture was poured into 100 mL of water and extracted with ethyl acetate. The organic layer was separated and washed once with water, slurried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrate was solidified with a small amount of hexane, slurried, and filtered to produce the pale yellow target compound S3-2 (0.64 g, 60.0% yield).

[0106] (3) Preparation of Compound S3 In a glove box, compound S3-2 (0.1 g, 0.3 mmol) was dissolved in 10 mL of toluene, followed by the addition of tetrabenzylhafnium (0.14 g, 0.3 mmol) and stirring at room temperature for 12 hours. Upon completion of the reaction, the mixture was heated to 50 °C and the solvent was removed under reduced pressure. The concentrated compound was then substituted with hexane to produce the target compound S3 (0.06 g, 27.3% yield) as an orange foam.

[0107] 1 H NMR (500MHz, CDCl3): 8.44 (d, 1H), 7.45 (d, 1H), 7.57 (t, 1H), 7.50 (t, 1H), 7.15~7.32 (m, 15H) ), 6.98(s, 2H), 3.45(t, 2H), 2.41(s, 6H), 2.36(s, 3H), 2.09(s, 6H), 2.0(m, 1H), 1.03(d, 6H)

[0108] Manufacturing Example 4 [ka]

[0109] The compounds were prepared according to the following method. [ka]

[0110] (1) Preparation of Compound S4-1 Using 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (5.0 g, 19.6 mmol) and naphthalen-1-ylboronic acid (3.54 g, 20.6 mmol), an experiment similar to that for the preparation of compound S3-1 was carried out to prepare the target compound S4-1 as a pale yellow solid (5.8 g, 85.0% yield).

[0111] (2) Preparation of Compound S4-2 Using compound S4-1 (2.73 g, 7.9 mmol) and propan-1-amine (1.29 mL, 15.7 mmol), an experiment similar to that described in the preparation example for compound S3-2 was carried out to prepare the target compound S4-2 as a pale yellow solid (2.42 g, yield 83.2%).

[0112] (3) Preparation of Compound S4 An experiment was carried out in a glove box using compound S4-2 (0.32 g, 0.9 mmol) in the same manner as in the preparation example of compound S1 to produce orange target compound S4 (0.15 g, yield 31.2%).

[0113] 1 H NMR (500MHz, CDCl3): 8.49 (d, 1H), 8.06 (d, 1H), 8.01 (d, 1H), 7.95 (d, 1H), 7.82 (d, 1H), 7.7 4(d, 1H), 7.62(d, 1H), 7.47~7.59(m, 4H), 3.62(q, 2H), 1.76(m, 2H), 1.07(t, 3H), 0.9(s, 9H)

[0114] Production Example 5 [ka]

[0115] The compounds were prepared according to the following method. [ka]

[0116] (1) Preparation of Compound S5-1 Using compound S3-1 (1.0 g, 3.0 mmol) and propan-1-amine (0.36 mL, 4.4 mmol), an experiment similar to that for the preparation of compound S3-2 was carried out to prepare the target compound S5-1 as a pale yellow solid (0.5 g, yield 46.9%).

[0117] (2) Preparation of Compound S5 An experiment was carried out in a glove box using compound S5-1 (0.50 g, 1.4 mmol) in the same manner as in the preparation example of compound S1 to produce orange target compound S5 (0.34 g, yield 42.1%).

[0118] 1 H NMR (500 MHz, CDCl): 8.50(d, 1H), 7.69(d, 1H), 7.58(t, 1H), 7.52(t, 1H), 6.94(s, 2H), 3.13( t, 2H), 2.40(s, 3H), 1.85(s, 6H), 1.60(m, 2H), 1.00(m, 3H), 0.93(s, 9H)

[0119] Manufacturing Example 6 [ka]

[0120] The compounds were prepared according to the following method. [ka]

[0121] An experiment was carried out in a glove box using compound S5-1 (0.1 g, 0.3 mmol) in the same manner as in the preparation example of compound S2 to prepare pale yellow target compound S6 (0.05 g, yield 38.9%).

[0122] 1 H NMR (500 MHz, CDCl): 8.50(d, 2H), 7.69(d, 2H), 7.58(t, 2H), 7.52(t, 2H), 6.94(s, 4H), 3.13( t, 4H), 2.40(s, 6H), 1.85(s, 12H), 1.60(m, 4H), 1.00(m, 6H), 0.90(s, 6H)

[0123] Manufacturing Example 7 [ka]

[0124] The compounds were prepared according to the following method. [ka]

[0125] In a glove box, compound S5-1 (0.1 g, 0.3 mmol) and tetrabenzylhafnium (0.08 g, 0.15 mmol) were added to 5 mL of toluene and stirred at room temperature for 12 hours. The mixture was concentrated under reduced pressure and then substituted with hexane twice to produce the dark orange target compound S7 (0.1 g, 65.1% yield).

[0126] 1 H NMR (500 MHz, CD): 8.48(d, 2H), 7.44(d, 2H), 6.92~7.13(m, 10H), 6.70(s, 4H), 6.52(d, 4H), 3. 19(m, 4H), 2.20(s, 6H), 1.95(s, 12H), 1.70(m, 4H), 1.48(s, 4H), 1.00(t, 6H)

[0127] Manufacturing Example 8 [ka]

[0128] The compounds were prepared according to the following method. [ka]

[0129] (1) Preparation of Compound S8-1 Carbazole (3.44 g, 20.6 mmol) was dissolved in 65 mL of tetrahydrofuran and cooled to 0°C. NaH (0.94 g, 23.5 mmol) was slowly added and stirred at the same temperature for 10 minutes. 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (5.0 g, 19.6 mmol) was added to the mixture and stirred at room temperature for 12 hours. The mixture was poured into 500 mL of water and extracted with dichloromethane. The organic layer was washed once more with water, separated, slurried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. A small amount of ethyl acetate was added to the concentrated compound to form a slurry, which was then filtered to produce the target compound S8-1 as a white solid (5.07 g, yield 67.0%).

[0130] (2) Preparation of Compound S8-2 Using compound S8-1 (2.0 g, 5.2 mmol) and propan-1-amine (0.64 mL, 7.8 mmol), an experiment similar to that described in the preparation example for compound S3-2 was carried out to prepare the target compound S8-2 as a pale yellow solid (1.7 g, yield 80.3%).

[0131] (3) Preparation of Compound S8 The same experiment as in the preparation example of compound S2 was carried out in a glove box using compound S8-2 (0.5 g, 1.2 mmol), to prepare the deep yellow target compound S8 (0.42 g, yield 67.0%).

[0132] 1 H NMR (500 MHz, CDCl): 8.47(d, 2H), 8.16(d, 4H), 7.75(m, 6H), 7.60(t, 2H), 7.52(t, 2H), 7.46( t, 4H), 7.38(t, 4H), 3.62(m, 4H), 1.78(q, 4H), 1.07(t, 6H), 0.90(s, 6H)

[0133] Manufacturing Example 9 [ka]

[0134] The compounds were prepared according to the following method. [ka]

[0135] The compound S4-2 (0.2 g, 0.5 mmol) was used in a glove box in the same manner as in the preparation example of compound S2 to produce the yellow target compound S9 (0.19 g, yield 78.8%).

[0136] 1 H NMR (500 MHz, CDCl): 8.49(d, 2H), 8.06(d, 2H), 8.01(d, 2H), 7.95(d, 2H), 7.82(d, 2H), 7.74(d, 2H), 7 .62(d, 2H), 7.47~7.59(m, 8H), 3.62(q, 4H), 1.76(m, 4H), 1.07(t, 6H), 0.9(s, 6H)

[0137] Comparative Manufacturing Example 1 [ka]

[0138] Comparative Production Example 1 was produced according to a method known in the literature [Organometallics 2011, 30, 12, 3318-3329].

[0139] Comparative Manufacturing Example 2 [ka]

[0140] The compounds were prepared according to the following method. [ka]

[0141] (1) Preparation of Compound C2-1 2-chloro-N-isobutyl-6-methylpyrimidin-4-amine (1.0 g, 5.0 mmol) and 2,4,6-trimethylphenyl boronic acid (0.86 g, 5.3 mmol) were dissolved in 60 mL of tetrahydrofuran, followed by the addition of 20 mL of aqueous K2CO3 (2.08 g, 15 mmol) and heating. Pd(PPh3)4 (0.12 g, 0.1 mmol) was added to the refluxing mixture and stirred for 12 hours. The reaction mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrated compound was recrystallized with MeOH to give a white solid product (1.4 g, 99% yield).

[0142] (2) Preparation of Compound C2 The compound C2-1 (0.2 g, 0.71 mmol) was used in a glove box in the same manner as in the preparation example of compound S2 to produce the yellow target compound C2 (0.12 g, 44% yield).

[0143] 1 H-NMR (500MHz, C6D6): 6.67(s, 4H), 5.26(s, 2H), 3.04(t, 4H), 2.07(s, 6H), 2.04(s, 6H), 1.87(s, 12H), 1.70(s, 6H), 1.41(m, 2H), 0.81(d, 12H)

[0144] <Polymerization of ethylene / α-olefin copolymer> Example 1 A 2L autoclave reactor was charged with hexane solvent (900 mL) and 1-octene (600 mL), and the reactor was preheated to 120°C. Simultaneously, the reactor was pre-charged with ethylene (35 bar). 3 μmol of a catalyst (a 3:1 mixture of the compounds from Preparation Example 1 and Preparation Example 2), 15 μmol of dimethylanilinium tetrakis(pentafluorophenyl)borate cocatalyst (AB) (10 eq relative to the catalyst), and 0.6 mmol 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.

[0145] [Table 1]

[0146] <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.

[0147] (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).

[0148] (2) Melt Index MI according to ASTM D-1238 2.16 (Condition E, 190°C, 2.16 kg load) was measured.

[0149] (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.

[0150] [Table 2]

[0151] As shown in Table 2, the Tm of the ethylene / α-olefin copolymer in the Examples was higher than that in Comparative Example 1, confirming that an ethylene / α-olefin copolymer with excellent heat resistance was produced. This effect is achieved by using the transition metal compound represented by 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 is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, Ring A is 【Chemistry 2】 or 【Transformation 3】 where R ２ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, ２ is substituted, it is substituted with an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, m is 1 and n is 3, or m is 2 and n is 2; Each X 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 alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms.

2. M is Hf; R １ is an alkyl group having 1 to 15 carbon atoms, R ２ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, ２ When substituted, it is substituted with an alkyl group having 1 to 15 carbon atoms, 2. The transition metal compound of claim 1, wherein m is 1 and n is 3.

3. M is Hf; R １ is an alkyl group having 1 to 15 carbon atoms, R ２ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, ２ When substituted, it is substituted with an alkyl group having 1 to 15 carbon atoms, 2. The transition metal compound of claim 1, wherein m is 2 and n is 2.

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. 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 In the chemical formulas 1-1 to 1-4, R １ is an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, R ２ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, ２ is substituted, it is substituted with an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 5 to 20 carbon atoms, Each X 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 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 Engineering 8A】 【Chemical 8B】 【Chemical 8C】 【8D】

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

7. The catalyst composition according to claim 6, further comprising a transition metal compound represented by the following Formula 2: 【Chemistry 9】 In the above Chemical Formula 2, Q is Ti, Zr, or Hf; R １３ ~R １６ are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and two or more adjacent groups thereof may be linked to form a ring; R １７ and R １８ are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution is with an alkyl group having 1 to 6 carbon atoms; R １９ are each independently an alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, n is 1 to 5; Y １ and Y ２ 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.

8. The catalyst composition according to claim 6, wherein the transition metal compound represented by Chemical Formula 2 is a compound represented by Chemical Formula 2A: 【Chemistry 10】 In the chemical formula 2A, Q is Ti, Zr, or Hf; R １７ and R １８ are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the substitution is with an alkyl group having 1 to 6 carbon atoms; R １９ are each independently an alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, Y １ and Y ２ 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.

9. 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.

10. A method for producing an olefin polymer, comprising the step of polymerizing an olefin monomer in the presence of the catalyst composition according to any one of claims 6 to 9.

11. The method for producing an olefin polymer according to claim 10, wherein the olefin polymer is an ethylene / α-olefin copolymer.

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