Transition metal compound, catalyst composition including the same, and preparation method of olefin polymer using the same

Abstract

Provided are a transition metal compound represented by the following Chemical Formula 1, a catalyst composition including the same, and a preparation method of an olefin polymer using the same, and an olefin polymer prepared by the preparation method: Formula (I) wherein M, R1 to R9, Ar1, Ar2, A, n, and m are as defined in the specification.

Description

TRANSITION METAL COMPOUND, CATALYST COMPOSITION INCLUDING THE SAME, AND PREPARATION METHOD OF OLEFIN POLYMER USING THE SAME

[0001] The present invention relates to a transition metal compound, a catalyst composition including the same, and a preparation method of an olefin polymer using the same.

[0002] When a metallocene catalyst is used in preparing a homopolymer of ethylene or a copolymer of ethylene with α-olefin, since it is a homogeneous catalyst having a single active site, it may produce an olefin polymer having a narrower molecular weight distribution and a more uniform composition distribution than a conventional Ziegler-Natta catalyst.

[0003] However, it is difficult to obtain a high molecular weight polymer using the metallocene catalyst system, and in particular, when the metallocene catalyst system is used in solution polymerization performed at a high temperature at 100°C or higher, polymerization activity is rapidly lowered. In addition, even when catalytic activity is improved to somewhat improve the problems described above, the solubility of the catalyst is not good, so that it is difficult to apply the catalyst to a solution polymerization process and apply it to an industrial site.

[0004] There is a need to develop a new catalyst which may solve the problems described above, secure high catalytic activity, and also satisfy excellent solubility and an ability to prepare a high molecular weight polymer.

[0005] An object of the present invention is to provide a transition metal compound having a novel structure which is useful as a catalyst for olefin polymerization, and a catalyst composition including the same.

[0006] Another object of the present invention is to provide a preparation method of an olefin polymer using the catalyst composition, and an olefin polymer prepared therefrom.

[0007] In one general aspect, a transition metal compound represented by the following Chemical Formula 1 is provided:

[0008] [Chemical Formula 1]

[0009]

[0010] wherein

[0011] M is a Group 4 transition metal;

[0012] A is (C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryl, (C6-C20)aryloxy, or (C1-C20)alkyl(C6-C20)aryloxy;

[0013] R1to R3are independently of one another hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, di(C6-C20)arylamino, (C1-C20)alkylthio, or (C6-C20)arylthio;

[0014] R1to R3are not hydrogen at the same time;

[0015] Ar1and Ar2are independently of each other (C6-C40)aryl;

[0016] R4and R5are independently of each other hydrogen, (C1-C20)alkyl, (C1-C20)alkoxy, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryloxy, (C2-C20)alkenyl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryl, (C6-C20)aryl(C2-C20)alkenyl, halogen, halo(C1-C20)alkyl, halo(C6-C20)aryl, or *-Si(Ra)(Rb)(Rc);

[0017] R6and R7are independently of each other (C1-C20)alkyl, (C1-C20)alkoxy, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryl, or *-Si(Ra)(Rb)(Rc), or may be connected to an adjacent substituent by (C3-C12)alkylene or (C3-C12)alkenylene to form an aliphatic ring or an aromatic ring;

[0018] Rato Rcare independently of one another hydrogen, (C1-C20)alkyl, (C1-C20)alkoxy, or (C6-C20)aryl;

[0019] n and m are independently of each other an integer of 0 to 3;

[0020] R8and R9are independently of each other (C1-C20)alkyl or (C6-C20)aryl, or R8and R9may be connected by (C3-C12)alkylene or (C3-C12)alkenylene to form an alicyclic ring or an aromatic ring; and

[0021] the alkyl, alkoxy, aryl, and aryloxy of A; the alkyl, haloalkyl, aryl, haloaryl, alkenyl, arylalkyl, and arylalkenyl of R4and R5; the alkyl, alkoxy, cycloalkyl, aryl, arylalkyl, alkylaryl, alicyclic ring, and aromatic ring of R6and R7; the alkyl and aryl of R8and R9; the aryl of Ar1and Ar2; and the alkyl and aryl of Rato Rcmay be substituted by one or more selected from (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, and di(C6-C20)arylamino.

[0022] A may be (C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryloxy, or (C6-C20)aryl(C1-C20)alkyl.

[0023] The transition metal compound according to an exemplary embodiment may be represented by the following Chemical Formula 2 or 3:

[0024] [Chemical Formula 2]

[0025]

[0026] [Chemical Formula 3]

[0027]

[0028] wherein

[0029] M, R4to R9, Ar1, Ar2, n, and m are as defined above in Chemical Formula 1;

[0030] R11and R12are independently of each other hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, di(C6-C20)arylamino, (C1-C20)alkylthio, or (C6-C20)arylthio;

[0031] R11and R12are not hydrogen at the same time; and

[0032] R15is (C1-C20)alkyl.

[0033] The transition metal compound according to an exemplary embodiment may be represented by the following Chemical Formula 4 or 5:

[0034] [Chemical Formula 4]

[0035]

[0036] [Chemical Formula 5]

[0037]

[0038] wherein

[0039] M is titanium, zirconium, or hafnium;

[0040] Ar1and Ar2are independently of each other (C6-C40)aryl, and the aryl of Ar1and Ar2may be substituted by (C1-C20)alkyl or (C6-C20)aryl;

[0041] R4and R5are independently of each other (C1-C20)alkyl;

[0042] R8and R9are independently of each other (C1-C20)alkyl or (C6-C20)aryl;

[0043] R11and R12are independently of each other hydrogen or (C1-C20)alkyl;

[0044] R11and R12are not hydrogen at the same time;

[0045] R21and R22are independently of each other hydrogen or (C1-C20)alkyl, or may be connected by (C2-C4)alkylene to form a ring; and

[0046] R15is (C1-C20)alkyl.

[0047] The transition metal compound according to an exemplary embodiment may be represented by the following Chemical Formula 6 or 7:

[0048] [Chemical Formula 6]

[0049]

[0050] [Chemical Formula 7]

[0051]

[0052] wherein

[0053] Ar1and Ar2are independently of each other (C6-C20)aryl, and the aryl of Ar1and Ar2may be substituted by (C1-C7)alkyl or (C6-C12)aryl;

[0054] R8and R9are independently of each other (C1-C7)alkyl or (C6-C12)aryl;

[0055] R11and R12are independently of each other hydrogen or (C8-C20)alkyl; and

[0056] R11and R12are not hydrogen at the same time.

[0057] The transition metal compound according to an exemplary embodiment may be selected from the following structures:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] .

[0066] The transition metal compound according to an exemplary embodiment may have a solubility in a hydrocarbon-based solvent at 25°C of 1 wt% or more.

[0067] In another general aspect, a transition metal catalyst composition for preparing an olefin polymer includes: a transition metal compound represented by the following Chemical Formula 1 and a cocatalyst:

[0068] [Chemical Formula 1]

[0069]

[0070] wherein

[0071] M, R1to R9, Ar1, Ar2, A, n, and m are as defined above.

[0072] The cocatalyst may include an aluminum compound, a boron compound, or a combination thereof.

[0073] In another general aspect, a preparation method of an olefin polymer includes: performing solution polymerization of an olefin monomer in the presence of a transition metal compound represented by the following Chemical Formula 1, a cocatalyst, and a hydrocarbon-based solvent to obtain an olefin polymer:

[0074] [Chemical Formula 1]

[0075]

[0076] wherein

[0077] M, R1to R9, Ar1, Ar2, A, n, and m are as defined above.

[0078] The hydrocarbon-based solvent may be one or two or more selected from non-aromatic hydrocarbon-based solvents including methylcyclohexane, cyclohexane, n-heptane, n-hexane, n-butane, isobutane, n-pentane, n-octane, isooctane, nonane, decane, and dodecane; and aromatic hydrocarbon-based solvents including toluene, benzene, ethylbenzene, xylene, naphthalene, methylnaphthalene, anthracene, acenaphthene, and phenanthrene.

[0079] A solubility of the transition metal compound in the hydrocarbon-based solvent at 25°C may be 1 wt% or more.

[0080] The cocatalyst may include an aluminum compound, a boron compound, or a mixture thereof.

[0081] The solution polymerization may be performed at a temperature of 70 to 200°C under 6 to 150 atm.

[0082] The olefin polymer may have a weight average molecular weight of 5,000 to 200,000 g / mol and a molecular weight distribution (Mw / Mn) of 1.0 to 10.0.

[0083] The olefin polymer may have an ethylene content of 20 to 99 wt%.

[0084] In still another general aspect, an olefin polymer prepared by the above preparation method is provided.

[0085] The transition metal compound according to an exemplary embodiment of the present invention may be useful as a catalyst for preparing an olefin polymer. Specifically, since the transition metal compound according to an exemplary embodiment has a significantly improved solubility in a hydrocarbon solvent, excellent catalytic activity, and excellent thermal stability, excellent catalytic activity may be maintained even in a high temperature environment. In particular, the transition metal compound according to an exemplary embodiment may be completely dissolved in a non-aromatic hydrocarbon-based solvent, has no usage limit depending on solubility, and is easily applied to a solution polymerization process.

[0086] In addition, the catalyst composition including the transition metal compound according to an exemplary embodiment may have excellent polymerization reactivity with an olefin-based monomer, for example, ethylene, α-olefin, other comonomers, and the like, and allows preparation of a high molecular weight polymer with high yield. That is, the transition metal compound according to an exemplary embodiment is used as a catalyst, thereby environmentally friendly and efficiently preparing an olefin polymer, and is expected to have excellent commercial practicality.

[0087] All terms used herein have the same meanings as those commonly understood by one of those skilled in the art to which the present invention pertains. The terms used herein are only for effectively describing a certain specific example, and are not intended to limit the present invention.

[0088] The singular form used in the present specification may be intended to also include a plural form, unless otherwise indicated in the context.

[0089] Throughout the present specification, unless otherwise particularly stated, "comprising", "being equipped with", "containing", or "having" a constituent element does not mean excluding any other constituent element, but mean further including other constituent elements, and elements, materials, or processes which are not further listed are not excluded.

[0090] The numerical range used in the present specification includes all values within the range including the lower limit and the upper limit, increments logically derived in a form and spanning in a defined range, all double limited values, and all possible combinations of the upper limit and the lower limit in the numerical range defined in different forms. Unless otherwise defined in the present specification, values which may be outside a numerical range due to experimental error or rounding off of a value are also included in the defined numerical range.

[0091] Unless otherwise particularly defined in the present specification, "about" may be considered as a value within 30%, 25%, 20%, 15%, 10%, or 5% of a stated value.

[0092] The term "alkyl" used in the present specification refers to a monovalent straight chain or branched chain saturated hydrocarbon radical consisting of only carbon and hydrogen atoms, and an example of the alkyl includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and the like, but is not limited thereto.

[0093] The term "aryl" described in the present specification is an organic radical derived from aromatic hydrocarbon by removal of one hydrogen, and includes a monocyclic or fused ring system containing appropriately 4 to 7, preferably 5 or 6 ring atoms in each ring, and even a form in which a plurality of aryls are linked by a single bond. A fused ring system may include an aliphatic ring such as saturated or partially saturated rings, and necessarily includes one or more aromatic rings. In addition, the aliphatic ring may contain nitrogen, oxygen, sulfur, carbonyl, and the like in the ring. An example of the aryl radical includes phenyl, naphtyl, biphenyl, indenyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, cricenyl, naphthacenyl, 9,10-dihydroanthracenyl, and the like, but is not limited thereto.

[0094] The term "cycloalkyl" described in the present specification refers to a monovalent saturated carbocyclic radical consisting of one or more rings. An example of the cycloalkyl radical includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like, but is not limited thereto.

[0095] The terms "alkoxy" and "aryloxy" described in the present specification refer to a *-O-alkyl radical and a *-O-aryl radical, respectively, in which "alkyl" and "aryl" are as defined above.

[0096] The terms "alkylthio" and "arylthio" described in the present specification refer to a *-S-alkyl radical and a *-S-aryl radical, respectively, in which "alkyl" and "aryl" are as defined above.

[0097] The term "arylalkyl" described in the present specification refers to alkyl substituted by one or more aryls, and as an example, may be benzyl and the like, but is not limited thereto.

[0098] The term "alkylaryl" described in the present specification refers to aryl substituted by one or more alkyls, and as an example, may be tolyl and the like, but is not limited thereto.

[0099] The term "alkylaryloxy" described in the present specification refers to aryloxy substituted by one or more alkyls.

[0100] The terms "halo" or "halogen" described in the present specification refers to fluorine, chlorine, bromine, iodine atom, or the like.

[0101] The terms "haloalkyl" and "haloaryl" described in the present specification refer to alkyl and aryl in which at least one or more hydrogens are substituted by halogen, respectively.

[0102] Hereinafter, the present disclosure will be described in detail. However, it is only illustrative and the present disclosure is not limited to the specific exemplary embodiment which is illustratively described.

[0103] An exemplary embodiment of the present invention provides a transition metal compound having a novel structure which is useful as a catalyst for olefin polymerization, and the transition metal compound according to an exemplary embodiment may be represented by the following Chemical Formula 1:

[0104] [Chemical Formula 1]

[0105]

[0106] wherein

[0107] M is a Group 4 transition metal;

[0108] A is (C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryl, (C6-C20)aryloxy, or (C1-C20)alkyl(C6-C20)aryloxy;

[0109] R1to R3are independently of one another hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, di(C6-C20)arylamino, (C1-C20)alkylthio, or (C6-C20)arylthio;

[0110] R1to R3are not hydrogen at the same time;

[0111] Ar1and Ar2are independently of each other (C6-C40)aryl;

[0112] R4and R5are independently of each other hydrogen, (C1-C20)alkyl, (C1-C20)alkoxy, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryloxy, (C2-C20)alkenyl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryl, (C6-C20)aryl(C2-C20)alkenyl, halogen, halo(C1-C20)alkyl, halo(C6-C20)aryl, or *-Si(Ra)(Rb)(Rc);

[0113] R6and R7are independently of each other (C1-C20)alkyl, (C1-C20)alkoxy, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryl, or *-Si(Ra)(Rb)(Rc), or may be connected to an adjacent substituent by (C3-C12)alkylene or (C3-C12)alkenylene to form an aliphatic ring or an aromatic ring;

[0114] Rato Rcare independently of one another hydrogen, (C1-C20)alkyl, (C1-C20)alkoxy, or (C6-C20)aryl;

[0115] n and m are independently of each other an integer of 0 to 3;

[0116] when n and m are an integer of 2 or more, each R6and each R7may be identical to or different from each other;

[0117] R8and R9are independently of each other (C1-C20)alkyl or (C6-C20)aryl, or R8and R9may be connected by (C3-C12)alkylene or (C3-C12)alkenylene to form an alicyclic ring or an aromatic ring; and

[0118] the alkyl, alkoxy, aryl, and aryloxy of A; the alkyl, haloalkyl, aryl, haloaryl, alkenyl, arylalkyl, and arylalkenyl of R4and R5; the alkyl, alkoxy, cycloalkyl, aryl, arylalkyl, alkylaryl, alicyclic ring, and aromatic ring of R6and R7; the alkyl and aryl of R8and R9; the aryl of Ar1and Ar2; and the alkyl and aryl of Rato Rcmay be substituted by one or more selected from (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, and di(C6-C20)arylamino.

[0119] The transition metal compound according to an exemplary embodiment is an ANSA-type catalyst and may be used as a catalyst for preparing an olefin polymer, for example, an ethylene homopolymer or a copolymer of ethylene and α-olefin.

[0120] Since transition metal compound according to an exemplary embodiment has the structural feature, for example, has an indenyl group having an aryl substituent and a phenoxy group having a substituent at a specific position, it may secure excellent catalytic activity and also implement significantly improved solubility in a hydrocarbon solvent, in particular, a non-aromatic hydrocarbon solvent.

[0121] As an example, when the substituent of the phenoxy group is positioned at carbons 2 and 6 of a phenoxy group in the transition metal compound, a range of applicable substituents is limited, so that there may be no effect on improvement of solubility in a non-aromatic hydrocarbon solvent, and even when the phenoxy group has no substituent, solubility may not be improved, and thus, it is difficult to implement the effect to be desired in the present invention.

[0122] As an example, when R1to R3are alkyl, the alkyl may be (C4-C20)alkyl or (C8-C20)alkyl, and better solubility may be implemented.

[0123] As an example, A may be (C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryloxy, or (C6-C20)aryl(C1-C20)alkyl.

[0124] As an example, A may be (C1-C7)alkyl, (C8-C20)alkyl(C6-C12)aryloxy, or (C6-C12)aryl(C1-C7)alkyl.

[0125] Specifically, the transition metal compound according to an exemplary embodiment may be represented by the following Chemical Formula 2 or 3:

[0126] [Chemical Formula 2]

[0127]

[0128] [Chemical Formula 3]

[0129]

[0130] wherein

[0131] M, R4to R9, Ar1, Ar2, n, and m are as defined above in Chemical Formula 1;

[0132] R11and R12are independently of each other hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, di(C6-C20)arylamino, (C1-C20)alkylthio, or (C6-C20)arylthio;

[0133] R11and R12are not hydrogen at the same time; and

[0134] R15is (C1-C20)alkyl.

[0135] When n and m are an integer of 2 or more, each R6and each R7may be connected by an adjacent substituent and (C3-C12)alkylene or (C3-C12)alkenylene to form an aliphatic ring or an aromatic ring.

[0136] As an example, n and m may be independently of each other an integer of 0 to 2, or an integer of 0 or 1.

[0137] Specifically, the transition metal compound according to an exemplary embodiment may be represented by the following Chemical formula 4 or 5, may implement better catalytic activity, and may adjust comonomer selectivity:

[0138] [Chemical Formula 4]

[0139]

[0140] [Chemical Formula 5]

[0141]

[0142] wherein

[0143] M is titanium, zirconium, or hafnium;

[0144] Ar1and Ar2are independently of each other (C6-C40)aryl, and the aryl of Ar1and Ar2may be substituted by (C1-C20)alkyl or (C6-C20)aryl;

[0145] R4and R5are independently of each other (C1-C20)alkyl;

[0146] R8and R9are independently of each other (C1-C20)alkyl or (C6-C20)aryl;

[0147] R11and R12are independently of each other hydrogen or (C1-C20)alkyl;

[0148] R11and R12are not hydrogen at the same time; and

[0149] R21and R22are independently of each other hydrogen or (C1-C20)alkyl, or may be connected by (C2-C4)alkylene to form a ring; and

[0150] R15is (C1-C20)alkyl.

[0151] As an example, R4and R5may be independently of each other (C1-C7)alkyl or (C1-C3)alkyl.

[0152] As an example, R4and R5are identical to each other and may be (C1-C7)alkyl or (C1-C3)alkyl.

[0153] As an example, R15may be (C1-C7)alkyl or (C1-C3)alkyl.

[0154] The transition metal compound according to an exemplary embodiment may be represented by the following Chemical Formula 6 or 7:

[0155] [Chemical Formula 6]

[0156]

[0157] [Chemical Formula 7]

[0158]

[0159] wherein

[0160] Ar1and Ar2are independently of each other (C6-C20)aryl, and the aryl of Ar1and Ar2may be substituted by (C1-C7)alkyl or (C6-C12)aryl;

[0161] R8and R9are independently of each other (C1-C7)alkyl or (C6-C12)aryl;

[0162] R11and R12are independently of each other hydrogen or (C8-C20)alkyl; and

[0163] R11and R12are not hydrogen at the same time.

[0164] Specifically, the transition metal compound according to an exemplary embodiment may be represented by the following Chemical Formulae 8 to 11:

[0165] [Chemical Formula 8]

[0166]

[0167] [Chemical Formula 9]

[0168]

[0169] [Chemical Formula 10]

[0170]

[0171] [Chemical Formula 11]

[0172]

[0173] wherein

[0174] Ar1and Ar2are independently of each other (C6-C20)aryl, and the aryl of Ar1and Ar2may be substituted by (C1-C7)alkyl or (C6-C12)aryl;

[0175] R8and R9are independently of each other (C1-C7)alkyl or (C6-C12)aryl; and

[0176] R11and R12are independently of each other (C8-C20)alkyl.

[0177] More specifically, the transition metal compound according to an exemplary embodiment may be selected from the following structures, but is not limited thereto:

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] In the above structure, t-Bu refers to ter-butyl (*-C(CH3)3), and t-Oc refers to tert-octyl ( ).

[0187] The transition metal compound according to an exemplary embodiment may have a solubility in a hydrocarbon-based solvent at 25°C of 1 wt% or more, specifically 5 wt% or more, 10 wt% or more, 5 to 50 wt%, 10 to 50 wt%, 10 to 40 wt%, or 10 to 30 wt%, and any possible combination of the upper limit and the lower limit in the numerical range.

[0188] The hydrocarbon-based solvent may be a non-aromatic hydrocarbon-based solvent, an aromatic hydrocarbon-based solvent, or a mixed solvent thereof, and the transition metal compound according to an exemplary embodiment may have excellent solubility in both the non-aromatic hydrocarbon-based solvent and the aromatic hydrocarbon-based solvent.

[0189] The non-aromatic hydrocarbon-based solvent may be selected from, for example, methylcyclohexane, cyclohexane, n-heptane, n-hexane, n-butane, isobutane, n-pentane, n-octane, isooctane, nonane, decane, dodecane, and the like. The aromatic hydrocarbon-based solvent may be selected from, for example, toluene, benzene, ethylbenzene, xylene, naphthalene, methylnaphthalene, anthracene, acenaphthene, phenanthrene, and the like, but is not limited thereto.

[0190] Another exemplary embodiment of the present invention provides a transition metal catalyst composition for preparing an olefin polymer including the transition metal compound according to an exemplary embodiment of the present invention, and the olefin polymer may be, for example, an ethylene homopolymer or a copolymer of ethylene and α-olefin.

[0191] Specifically, the transition metal catalyst composition according to an exemplary embodiment may include a transition metal compound represented by the following Chemical Formula 1 and a cocatalyst:

[0192] [Chemical Formula 1]

[0193]

[0194] wherein M, R1to R9, Ar1, Ar2, A, n, and m are as defined above.

[0195] Since the transition metal compound represented by Chemical Formula 1 is as described above, detailed description thereof will be omitted.

[0196] The cocatalyst may include an aluminum compound, a boron compound, or a combination thereof.

[0197] A boron compound which may be used as the cocatalyst may be a boron compound known in U.S. Patent Publication No. 5,198,401, but, specifically, may be selected from the compounds represented by the following Chemical Formulae 21 to 24:

[0198] [Chemical Formula 21]

[0199] BR313

[0200] [Chemical Formula 22]

[0201] [R32]+[BR314]-

[0202] [Chemical Formula 23]

[0203] [R33pZH]+[BR314]-

[0204] [Chemical Formula 24]

[0205]

[0206] wherein

[0207] B is a boron atom;

[0208] R31is independently of each other phenyl unsubstituted or substituted by one or more selected from the group consisting of fluoro, (C1-C20)alkyl, fluoro(C1-C20)alkyl, (C1-C20)alkoxy, and fluoro(C1-C20)alkoxy;

[0209] R32is a (C5-C7)aromatic radical, a (C1-C20)alkyl(C6-C20)aryl radical, or a (C6-C20)aryl(C1-C20)alkyl radical;

[0210] Z is a nitrogen or phosphorus atom;

[0211] R33is independently of each other a (C1-C20)alkyl radical or an anilinium radical substituted by two (C1-C10)alkyls with a nitrogen atom;

[0212] R34is (C5-C20)alkyl;

[0213] R35is (C5-C20)aryl or (C1-C20)alkyl(C6-C20)aryl; and

[0214] p is an integer of 2 or 3.

[0215] A preferred example of the boron compound may include trityl tetrakis(pentafluorophenyl)borate, tris(pentafluorophenyl)borane, tris(2,3,5,6-tetrafluorophenyl)borane, tris(2,3,4,5-tetrafluorophenyl)borane, tris(3,4,5-trifluorophenyl)borane, tris(2,3,4-trifluorophenyl)borane, phenyl bis(pentafluorophenyl)borane, tetrakis(pentafluorophenyl)borate, tetrakis(2,3,5,6-tetrafluorophenyl)borate, tetrakis(2,3,4,5-tetrafluorophenyl)borate, tetrakis(3,4,5-trifluorophenyl)borate, tetrakis(2,2,4-trifluorophenyl)borate, phenyl bis(pentafluorophenyl)borate, or tetrakis(3,5-bistrifluoromethylphenyl)borate. In addition, an example of the specific combination thereof may include ferrocenium tetrakis(pentafluorophenyl)borate, 1,1'-dimethylferrocenium tetrakis(pentafluorophenyl)borate, silver tetrakis(pentafluorophenyl)borate, triphenylmethyl tetrakis(pentafluorophenyl)borate, triphenyl methyl tetrakis(3,5-bistrifluoromethylphenyl)borate, triethylammonium tetrakis(pentafluorophenyl)borate, tripropylammonium tetrakis(pentafluorophenyl)borate, tri-n-butylammonium tetrakis(pentafluorophenyl)borate, tri-n-butylammonium tetrakis(3,5-bistrifluoromethylphenyl)borate, N,N-dimethylanilinium tetrakis(pentafluorophenyl)borate, N,N-diethylanilinium tetrakis(pentafluorophenyl)borate, N,N-2,4,6-pentamethylanilinium tetrakis(pentafluorophenyl)borate, N,N-dimethylanilinium tetrakis(3,5-bistrifluoromethylphenyl)borate, diisopropylammonium tetrakis(pentafluorophenyl)borate, dicyclohexylammonium tetrakis(pentafluorophenyl)borate, triphenylphosphonium tetrakis(pentafluorophenyl)borate, trimethylphenylphosphonium tetrakis(pentafluorophenyl)borate, or tridimethylphenylphosphonium tetrakis(pentafluorophenyl)borate, and among them, any one or two or more selected from trityl tetrakis(pentafluorophenyl)borate, N,N-dimethylanilium tetrakis(pentafluorophenyl)borate, triphenylmethylinum tetrakis(pentafluorophenyl)borate, and tris pentafluoroborane may be most preferred.

[0216] An example of an aluminum compound which may be used as the cocatalyst in the catalyst composition according to an exemplary embodiment of the present invention may be an aluminoxane compound of the following Chemical Formula 31 or 32, an organoaluminum compound of the following Chemical Formula 33, or an organoaluminum alkyl oxide or organoaluminum aryl oxide compound of the following Chemical Formula 34 or 35:

[0217] [Chemical Formula 31]

[0218] -(Al(R51)-O)m-

[0219] [Chemical Formula 32]

[0220] (R52)2Al-(-O(R52)-)q-O-Al(R52)2

[0221] [Chemical Formula 33]

[0222] (R53)rAl(E)3-r

[0223] [Chemical Formula 34]

[0224] (R54)2AlOR55

[0225] [Chemical Formula 35]

[0226] R54Al(OR55)2

[0227] wherein

[0228] R31and R32are independently of each other C1-C20alkyl;

[0229] m and q are an integer of 5 to 20;

[0230] R33and R34are independently of each other C1-C20alkyl;

[0231] E is a hydrogen atom or a halogen atom;

[0232] r is an integer of 1 to 3; and

[0233] R35is C1-C20alkyl or C6-C30aryl.

[0234] The aluminum compound may be, specifically, one or a mixture of two or more selected from aluminoxane and organoaluminum compounds.

[0235] A specific examples of the compound which may be used as the aluminum compound may include aluminoxane compounds such as methylaluminoxane, modified methylaluminoxane, and tetraisobutylaluminoxane; organoaluminum compounds, for example, trialkylaluminum including trimethylaluminum, triethylaluminum, tripropylaluminum, triisobutylaluminum, and trihexylaluminum; dialkylaluminum chloride including dimethylaluminum chloride, diethylaluminum chloride, dipropylaluminum chloride, diisobutylaluminum chloride, and dihexylaluminum chloride; alkylaluminum dichloride including methylaluminum dichloride, ethylaluminum dichloride, propylaluminum dichloride, isobutylaluminum dichloride, and hexylaluminum dichloride; dialkylaluminum hydride including dimethylaluminum hydride, diethylaluminum hydride, dipropylaluminum hydride, diisobutylaluminum hydride, and dihexylaluminum hydride; alkylalkoxyaluminum including methyldimethoxyaluminum, dimethylmethoxyaluminum, ethyldiethoxyaluminum, diethylethoxyaluminum, isobutyldibuthoxyaluminum, diisobutylbutoxyaluminum, hexyldimethoxyaluminum, dihexylmethoxyaluminum, and dioctylmethoxyaluminum, preferably a compound alone selected from methylaluminoxane, modified methylaluminoxane, tetraisobutylaluminoxane, and trialkylaluminum, or a mixture thereof, more preferably trialkylaluminum, and still more preferably triethylaluminum or triisobutylaluminum.

[0236] The aluminum compound may be, more specifically, one or a mixture of two or more selected from methylaluminoxane, modified methylaluminoxane, tetraisobutylaluminoxane, trimethylaluminum, triethylaluminum, trioctylaluminum, triisobutylaluminum, and the like.

[0237] In the catalyst composition according to an exemplary embodiment, when the boron compound is included as the cocatalyst, a ratio between the transition metal compound and the boron may be in a range of 1:0.1 to 100, 1:0.5 to 30, or 1:0.5 to 10, as a mole ratio of the transition metal (M):boron atom (B).

[0238] In the catalyst composition according to an exemplary embodiment, when the aluminum compound is included as the cocatalyst, a ratio between the transition metal compound and the aluminum compound may be 1:1 to 2,000, 1:1 to 1,000, 1:1 to 500, or 1:10 to 500, as a mole ratio of the transition metal (M):aluminum atom (A1).

[0239] Another exemplary embodiment provides a preparation method of an olefin polymer using the transition metal compound according to an exemplary embodiment of the present disclosure.

[0240] The preparation method of an olefin polymer according to an exemplary embodiment may include: performing solution polymerization of an olefin monomer in the presence of a transition metal compound represented by Chemical Formula 1, a cocatalyst, and a hydrocarbon-based solvent to obtain an olefin polymer.

[0241] The hydrocarbon-based solvent may be one or two or more selected from non-aromatic hydrocarbon-based solvents including methylcyclohexane, cyclohexane, n-heptane, n-hexane, n-butane, isobutane, n-pentane, n-octane, isooctane, nonane, decane, and dodecane; and aromatic hydrocarbon-based solvents including toluene, benzene, ethylbenzene, xylene, naphthalene, methylnaphthalene, anthracene, acenaphthene, and phenanthrene.

[0242] Specifically, the hydrocarbon-based solvent may be a mixed solvent of the non-aromatic hydrocarbon-based solvent and the aromatic hydrocarbon-based solvent.

[0243] The transition metal compound according to an exemplary embodiment may have a solubility in a hydrocarbon-based solvent at 25°C of 1 wt% or more, specifically 5 wt% or more, 10 wt% or more, 5 to 50 wt%, 10 to 50 wt%, 10 to 40 wt%, or 10 to 30 wt%, and any possible combination of the upper limit and the lower limit in the numerical range.

[0244] The cocatalyst may be selected from the aluminum compounds, the boron compounds, or mixtures thereof, and the cocatalyst may be included at a mole ratio of 0.5 to 10,000, 0.5 to 5000, or 0.5 to 2000 with respect to 1 mol of the transition metal compound according to an exemplary embodiment, and since the description of the aluminum compound and the boron compound is as described above, it will be omitted.

[0245] The preparation method of an olefin polymer using the transition metal catalyst composition for preparing an olefin polymer may be performed by bringing the transition metal compound according to an exemplary embodiment, the cocatalyst, and the olefin monomer into contact in the presence of the hydrocarbon-based solvent. Herein, the transition metal compound and the cocatalyst components may be added to a reactor separately, or each component may be mixed in advance and added to a reactor, and mixing conditions such as an addition order, temperature or concentration are not particularly limited.

[0246] The olefin monomer may include ethylene or ethylene and comonomer, and the comonomer may be α-olefin.

[0247] Specifically, when an ethylene homopolymer is prepared using ethylene alone as the olefin monomer, the appropriate pressure of ethylene may be 1 to 1,000 atm, 1 to 500 atom, or 1 to 200 atm, preferably 6 to 150 atm. In addition, the polymerization reaction may be performed at 25°C to 220°C, 70°C to 220°C, 70°C to 200°C, or 100°C to 220°C.

[0248] In addition, when a copolymer of ethylene and α-olefin is prepared by including ethylene and α-olefin as an olefin monomer, as the α-olefin comonomer, for example, C3-C20 α-olefin; C4-C20 diolefin; C5-C20 cycloolefin or cyclodiolefin; styrene and a derivative thereof; and the like may be used. In addition, a preferred example of the C3-C20 α-olefin may be selected from propylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-hexadecene, 1-octadecene, and the like, a preferred example of the C4-C20 diolefin may be selected from 1,3-butadiene, 1,4-pentadiene, 2-methyl-1,3-butadiene, and the like, and a preferred example of the C5-C20 cycloolefin or cyclodiolefin may be selected from cyclopentene, cyclohexene, cyclopentadiene, cyclohexadiene, norbornene, 5-vinylidene-2-norbornene (VNB), 5-methylene-2-norbornene (MNB), 5-ethylidene-2-norbornene (ENB), and the like, but they are not limited thereto.

[0249] In this case, a preferred ethylene pressure and a polymerization reaction temperature may be as described for the preparation of the ethylene homopolymer, and the olefin polymer prepared according to the method of the present invention may contain ethylene in a range of 30 wt% or more, 60 wt% or more, more preferably 60 to 99 wt%.

[0250] As described above, when the catalyst composition according to an exemplary embodiment of the present invention is used, ethylene, and α-olefin, for example, C3-C20 α-olefin or C3-C10 α-olefin as the comonomer may be appropriately used to easily and economically prepare from an elastomer having a density of 0.850 g / cc to 0.960 g / cc and a melt flow rate of 0.001 to 2.000 dg / min to a high-density polyethylene (HDPE) range.

[0251] When the olefin polymer according to an exemplary embodiment of the present invention is prepared, hydrogen may be used as a molecular weight modifier in order to adjust a molecular weight, and the olefin polymer prepared from the preparation method according to an exemplary embodiment may have a weight average molecular weight (Mw) in a range of 5,000 to 1,000,000 g / mol, in a range of 5,000 to 500,000 g / mol, or in a range of 5,000 to 200,000 g / mol.

[0252] Since the catalyst composition suggested in the present invention is present in a uniform form in a polymerization reactor, it is preferred to apply the composition to a solution polymerization process performed at a melting point or higher of the polymer, but the composition may be used a slurry polymerization or gaseous polymerization process, of course.

[0253] Hereinafter, the exemplary embodiments described above will be described in detail through the following examples. However, the following examples are only for description, and do not limit the right scope.

[0254] [Example 1]Preparation of transition metal compound 1

[0255]

[0256] Dimethylsilylenebis(2-methyl-4-phenylindenyl)zirconium dichloride (product from S-PCI, 5.0 g, 7.95 mmol) was dissolved in 100 mL of toluene, in a 250 mL round flask in a nitrogen atmosphere. The temperature was lowered to -15°C, 1.5 M methyllithium (10.6 mL, 15.9 mmol) was slowly injected, the temperature was raised to room temperature, and stirring was performed for 3 hours. 3-Dodecylphenol (4.84 g, 15.9 mmol) was added thereto under vigorous stirring, the stirring was performed at 80°C for 3 hours, and the solvent was removed under reduced pressure. The product was dissolved in 200 mL of n-hexane, and filtered through a filter filled with dried celite to remove a solid content. The solvent of the filtrate was all removed to obtain a yellow transition metal compound (Compound 1) (8.52 g, yield: 92.0%).

[0257] 1H NMR (CDCl3, 500 MHz): δ = 7.25-7.61 (m, 16H), 7.05-7.24 (m, 8H), 6.86 (s, 2H), 2.05-2.15 (m, 10H), 1.05-1.60 (m, 58H), 0.89-0.91 (m, 6H).

[0258] [Example 2]Preparation of transition metal compound 2

[0259]

[0260] A transition metal compound (Compound 2) was prepared (8.13 g, yield: 93.7%) in the same manner as in Example 1, except that dimethylsilylenebis(2-methyl-4-naphtylindenyl)zirconium dichloride was used instead of dimethylsilylenebis(2-methyl-4-phenylindenyl)zirconium dichloride

[0261] 1H NMR (CDCl3, 500 MHz): δ = 7.35-7.92 (m, 20H), 7.16-7.28 (m, 8H), 6.92 (s, 2H), 2.13-2.25 (m, 10H), 1.13-1.62 (m, 58H), 0.88-0.91 (m, 6H).

[0262] [Comparative Example 1]

[0263]

[0264] Dimethylsilylenebis(2-methyl-4-phenylindenyl)zirconium dichloride was purchased from S-PCI to prepare a transition metal compound (C1) of Comparative Example 1.

[0265] [Comparative Example 2]

[0266]

[0267] A transition metal compound (Compound C2) of Comparative Example 2 was prepared (5.21 g, yield: 88.1%) in the same manner as in Example 1, except that 2,6-dimethylphenol was used instead of 3-dodecylphenol.

[0268] 1H NMR (CDCl3, 500 MHz): δ = 7.25-7.60 (m, 16H), 7.01-7.12 (m, 6H), 6.85 (s, 2H), 2.15 (s, 12H), 1.53 (s, 6H), 0.88 (s, 6H).

[0269] [Comparative Example 3]

[0270]

[0271] A transition metal compound (Compound C3) of Comparative Example 3 was prepared (13.1 g, yield: 92.9%) in the same manner as in Example 1, except that phenol was used instead of 3-dodecylphenol.

[0272] 1H NMR (CDCl3, 500 MHz): δ = 7.21-7.52 (m, 16H), 7.01-7.22 (m, 10H), 6.83 (s, 2H), 1.55 (s, 6H), 0.89 (s, 6H).

[0273] [Experimental Example 1]Evaluation of solubility

[0274] 1 g of the transition metal compounds prepared in the examples and the comparative examples was dissolved in 1 g of each solvent (toluene, hexane) described in the following Table 1 to prepare a saturated solution, and a solid was removed through a filter of 0.45 μm. Next, the solvent was all removed, the remaining transition metal compound was weighed, and the solubility of the transition metal compound was calculated therefrom and is shown in the following Table 1. When the transition metal compound was not dissolved (insoluble) in the solvent, it was indicated as "-".

[0275] Solubility (wt%)Toluenen-HexaneExample 122.110.3Example 219.010.1Comparative Example 10.1-Comparative Example 21.3-Comparative Example 30.5-

[0276] As shown in Table 1, it was found that the solubility in the hydrocarbon solvent of the transition metal compounds prepared in Examples 1 and 2 was much higher than that of the transition metal compounds prepared in Comparative Examples 1 to 3, and, in particular, surprisingly improved solubility in hexane which is a non-aromatic hydrocarbon solvent was shown.

[0277] <Preparation of olefin polymer>

[0278] [Example 3]Copolymerization of ethylene and 1-octene

[0279] 600 mL of cyclohexane and 50 mL of 1-octene were added to a stainless-steel reactor having a volume of 1500 mL which was sufficiently dried and then nitrogen-substituted, and 2 mL of triisobutylaluminum (1.0 M hexane solution) was added to the reactor. Thereafter, the temperature of the reactor was raised up to 100°C, and 2.3 g of a toluene solution of 0.1 wt% of the transition metal compound prepared in Example 1 was added. Thereafter, 3.7 g of the toluene solution of 1.0 wt% of trityl tetrakis(pentafluorophenyl) borate was added, the reactor was filled with ethylene to the pressure inside of 20 kg / cm2, and then ethylene was continuously supplied to perform polymerization. The reaction was performed for 5 minutes to recover a reaction product, which was dried in a vacuum oven at 40°C for 8 hours. A catalyst temperature change (△T) and a catalytic activity (weight of produced polymer-kg / amount of catalyst used-mmol) during the polymerization process were analyzed and are described in the following Table 2.

[0280] [Example 4]

[0281] Polymerization was performed in the same manner as in Example 3, except that the transition metal compound of Example 2 was used instead of the transition metal compound of Example 1, as the transition metal compound. A catalyst temperature change (△T) and a catalytic activity (weight of produced polymer-kg / amount of catalyst used-mmol) during the polymerization process were analyzed and are described in the following Table 2.

[0282] [Comparative Example 4]

[0283] Polymerization was performed in the same manner as in Example 3, except that the transition metal compound of Comparative Example 1 (Compound C1) was used instead of the transition metal compound of Example 1, as the transition metal compound. A catalyst temperature change (△T) and a catalytic activity (weight of produced polymer-kg / amount of catalyst used-mmol) during the polymerization process were analyzed and are described in the following Table 2.

[0284] [Comparative Example 5]

[0285] Polymerization was performed in the same manner as in Example 3, except that the transition metal compound of Comparative Example 2 (Compound C2) was used instead of the transition metal compound of Example 1, as the transition metal compound. A catalyst temperature change (△T) and a catalytic activity (weight of produced polymer-kg / amount of catalyst used-mmol) during the polymerization process were analyzed and are described in the following Table 2.

[0286] [Comparative Example 6]

[0287] Polymerization was performed in the same manner as in Example 3, except that the transition metal compound of Comparative Example 3 (Compound C3) was used instead of the transition metal compound of Example 1, as the transition metal compound. A catalyst temperature change (△T) and a catalytic activity (weight of produced polymer-kg / amount of catalyst used-mmol) as the transition metal compound were analyzed and are described in the following Table 2.

[0288] Transition metal compound△T (°C)Catalytic activity (kg / mmol)Example 3Example 142.727.5Example 4Example 243.528.6Comparative Example 4Comparative Example 143.428.6Comparative Example 5Comparative Example 242.127.1Comparative Example 6Comparative Example 342.327.3

[0289] It was found from Tables 1 and 2 that the transition metal compounds of Examples 1 and 2 had significantly improved solubility in the non-aromatic hydrocarbon solvent as compared with the transition metal compounds of Comparative Examples 1 to 3 and may implement excellent catalytic activity.

[0290] Thus, the transition metal compounds according to the examples of the present invention have significantly increased solubility in a non-aromatic hydrocarbon solvent and may maintain catalytic activity for a polymerization reaction at a similar level, by introducing phenoxy having a substituent at a specific position, and thus, an olefin polymer may be prepared easily by a solution process. Therefore, an economic saving effect may be brought to the industrial process and also a conventional aromatic solvent, which may be harmful to the environment and the human body, may be replaced, by using the transition compound, and thus, it is environmentally friendly and effective.

[0291] Hereinabove, although the present invention has been described by specific exemplary embodiments, they have been provided only for assisting in the entire understanding of the present invention. Therefore, the present invention is not limited to the exemplary embodiments. Various modifications and changes may be made by those skilled in the art to which the present invention pertains from this description.

[0292] Therefore, the spirit of the present invention should not be limited to the above-described exemplary embodiments, and the following claims as well as all modifications equal or equivalent to the claims are intended to fall within the scope and spirit of the invention.

Claims

A transition metal compound represented by the following Chemical Formula 1:[Chemical Formula 1]whereinM is a Group 4 transition metal;A is (C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryl, (C6-C20)aryloxy, or (C1-C20)alkyl(C6-C20)aryloxy;R1to R3are independently of one another hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, di(C6-C20)arylamino, (C1-C20)alkylthio, or (C6-C20)arylthio;R1to R3are not hydrogen at the same time;Ar1and Ar2are independently of each other (C6-C40)aryl;R4and R5are independently of each other hydrogen, (C1-C20)alkyl, (C1-C20)alkoxy, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryloxy, (C2-C20)alkenyl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryl, (C6-C20)aryl(C2-C20)alkenyl, halogen, halo(C1-C20)alkyl, halo(C6-C20)aryl, or *-Si(Ra)(Rb)(Rc);R6and R7are independently of each other (C1-C20)alkyl, (C1-C20)alkoxy, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryl, or *-Si(Ra)(Rb)(Rc), or may be connected to an adjacent substituent by (C3-C12)alkylene or (C3-C12)alkenylene to form an aliphatic ring or an aromatic ring;Rato Rcare independently of one another hydrogen, (C1-C20)alkyl, (C1-C20)alkoxy, or (C6-C20)aryl;n and m are independently of each other an integer of 0 to 3;R8and R9are independently of each other (C1-C20)alkyl or (C6-C20)aryl, or R8and R9may be connected by (C3-C12)alkylene or (C3-C12)alkenylene to form an alicyclic ring or an aromatic ring; andthe alkyl, alkoxy, aryl, and aryloxy of A; the alkyl, haloalkyl, aryl, haloaryl, alkenyl, arylalkyl, and arylalkenyl of R4and R5; the alkyl, alkoxy, cycloalkyl, aryl, arylalkyl, alkylaryl, alicyclic ring, and aromatic ring of R6and R7; the alkyl and aryl of R8and R9; the aryl of Ar1and Ar2; and the alkyl and aryl of Rato Rcmay be substituted by one or more selected from (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, and di(C6-C20)arylamino.The transition metal compound of claim 1, wherein A is (C1-C20)alkyl, (C1-C20)alkyl(C6-C20)aryloxy, or (C6-C20)aryl(C1-C20)alkyl.The transition metal compound of claim 1, wherein the transition metal compound is represented by the following Chemical Formula 2 or 3:[Chemical Formula 2][Chemical Formula 3]whereinM, R4to R9, Ar1, Ar2, n, and m are as defined in claim 1;R11and R12are independently of each other hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, (C6-C20)aryl, (C6-C20)aryl(C1-C20)alkyl, (C1-C20)alkoxy, (C6-C20)aryloxy, mono(C1-C20)alkylamino, di(C1-C20)alkylamino, mono(C6-C20)arylamino, di(C6-C20)arylamino, (C1-C20)alkylthio, or (C6-C20)arylthio;R11and R12are not hydrogen at the same time; andR15is (C1-C20)alkyl.The transition metal compound of claim 1, wherein the transition metal compound is represented by the following Chemical Formula 4 or 5:[Chemical Formula 4][Chemical Formula 5]whereinM is titanium, zirconium, or hafnium;Ar1and Ar2are independently of each other (C6-C40)aryl, and the aryl of Ar1and Ar2may be substituted by (C1-C20)alkyl or (C6-C20)aryl;R4and R5are independently of each other (C1-C20)alkyl;R8and R9are independently of each other (C1-C20)alkyl or (C6-C20)aryl;R11and R12are independently of each other hydrogen or (C1-C20)alkyl;R11and R12are not hydrogen at the same time; andR21and R22are independently of each other hydrogen or (C1-C20)alkyl, or may be connected by (C2-C4)alkylene to form a ring; andR15is (C1-C20)alkyl.The transition metal compound of claim 1, wherein the transition metal compound is represented by the following Chemical Formula 6 or 7:[Chemical Formula 6][Chemical Formula 7]whereinAr1and Ar2are independently of each other (C6-C20)aryl, and the aryl of Ar1and Ar2may be substituted by (C1-C7)alkyl or (C6-C12)aryl;R8and R9are independently of each other (C1-C7)alkyl or (C6-C12)aryl;R11and R12are independently of each other hydrogen or (C8-C20)alkyl; andR11and R12are not hydrogen at the same time.The transition metal compound of claim 1, wherein the transition metal compound is selected from the following structures:The transition metal compound of claim 1, wherein the transition metal compound has a solubility in a hydrocarbon-based solvent at 25°C of 1 wt% or more.A transition metal catalyst composition for preparing an olefin polymer, comprising a transition metal compound represented by the following Chemical Formula 1 and a cocatalyst:[Chemical Formula 1]whereinM, R1to R9, Ar1, Ar2, n, and m are as defined in claim 1.A transition metal catalyst composition for preparing an olefin polymer of claim 8, wherein the cocatalyst includes an aluminum compound, a boron compound, or a combination thereof.A preparation method of an olefin polymer, the method comprising: performing solution polymerization of an olefin monomer in the presence of a transition metal compound represented by the following Chemical Formula 1, a cocatalyst, and a hydrocarbon-based solvent to obtain an olefin polymer:[Chemical Formula 1]whereinM, R1to R9, Ar1, Ar2, n, and m are as defined in claim 1.The preparation method of an olefin polymer of claim 10, wherein the hydrocarbon-based solvent is one or two or more selected from non-aromatic hydrocarbon-based solvents including methylcyclohexane, cyclohexane, n-heptane, n-hexane, n-butane, isobutane, n-pentane, n-octane, isooctane, nonane, decane, and dodecane; and aromatic hydrocarbon-based solvents including toluene, benzene, ethylbenzene, xylene, naphthalene, methylnaphthalene, anthracene, acenaphthene, and phenanthrene.The preparation method of an olefin polymer of claim 10, wherein a solubility of the transition metal compound in the hydrocarbon-based solvent at 25°C is 1 wt% or more.The preparation method of an olefin polymer of claim 10, wherein the cocatalyst includes an aluminum compound, a boron compound, or a mixture thereof.The preparation method of an olefin polymer of claim 10, wherein the solution polymerization is performed at a temperature of 70 to 200°C under 6 to 150 atm.The preparation method of an olefin polymer of claim 10, wherein the olefin polymer has a weight average molecular weight of 5,000 to 200,000 g / mol and a molecular weight distribution (Mw / Mn) of 1.0 to 10.0.The preparation method of an olefin polymer of claim 10, wherein the olefin polymer has an ethylene content of 20 to 99 wt%.An olefin polymer prepared from the preparation method of any one of claims 10 to 16.

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