Olefin polymerization procatalysts and their uses.

Abstract

The present invention relates to a procatalyst for olefin polymerization comprising a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor, wherein the internal electron donor is an iminodiacetate compound, and a method for preparing the procatalyst. The disclosure further relates to a catalyst system for olefin polymerization comprising the procatalyst, a cocatalyst, and an external electron donor, a method for preparing the catalyst system, and a method for olefin (co)polymerization using the catalyst system. The disclosure also relates to the iminodiacetate compound and its use as an internal electron donor in an olefin polymerization catalyst.

Description

[Technical Field]

[0001] The present disclosure relates to the field of olefin polymerization. In particular, the present invention relates to a procatalyst for olefin polymerization, comprising a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor that is an iminodiacetate compound, and a method for preparing the same. More particularly, the present disclosure relates to a catalyst system containing the procatalyst, a cocatalyst, and an external electron donor, a method for preparing the catalyst system, and a method for olefin (co)polymerization using the catalyst system. The present disclosure also relates to the iminodiacetate compound and its use as an internal electron donor in a catalyst for olefin polymerization. [Background technology]

[0002] Currently, olefin-based polymers are used in a wide variety of applications, resulting in a constantly increasing market demand for them. The use of Ziegler-Natta catalysts for the preparation of olefin-based polymers has been known in the art for many years. Generally, Ziegler-Natta catalysts include (i) a procatalyst containing a transition metal halide (e.g., a titanium, chromium, or vanadium halide compound) and an internal electron donor, both supported on a magnesium compound; and (ii) a cocatalyst, typically an organoaluminum compound. A preferred class of internal donors, widely used in the art, is represented by phthalate esters. Catalysts using phthalate esters as internal donors exhibit satisfactory activity and can produce polymers with suitable stereoregularity.

[0003] One of the problems associated with using phthalate compounds as internal donors is their poor environmental acceptability and their serious impact on human health. Therefore, all applications involving human contact with these compounds must be strictly restricted.

[0004] Therefore, there is a need for new internal donors for use with Ziegler-Natta catalysts that do not contain phthalates and pose no risk to either human health or the environment, while at the same time ensuring high catalytic activity and high isotacticity of the resulting polymers, commonly expressed as xylene solubles (XS).In addition to these properties, it is also desirable to provide an internal donor that is comparable to, for example, phthalates, but is more environmentally friendly, with a significantly simpler synthetic route for the new internal donors. DISCLOSURE OF THE INVENTION [Problem to be solved by the invention]

[0005] An object of the present disclosure is to provide a novel phthalate-free procatalyst for olefin (co)polymerization, comprising a novel internal electron donor. Another object of the present disclosure is to provide a novel procatalyst with good catalytic performance, in particular a novel procatalyst with improved catalytic activity that can produce polymers with high isotacticity. Another object of the present disclosure is to provide an internal electron donor that has a very simple synthetic route and provides an internal donor that is comparable to, for example, phthalates, but is more environmentally friendly.

[0006] Thus, there is also provided the use of an internal electron donor in a procatalyst for the (co)polymerization of olefins, in particular n-propylene, wherein the internal electron donor is an iminodiacetate compound. [Means for solving the problem]

[0007] In one aspect, there is provided a procatalyst for olefin polymerization comprising a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor which is a compound of formula (I): The internal electron donor has the formula (I) The compound is TIFF2025539733000001.tif35169. During the ceremony, R 1 is one or more identical or different substituents R 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 2 , R 3 , R 4 and R 5 is hydrogen, one or more identical or different substituents R 8 R is independently selected from the group consisting of alkyl, cycloalkyl, and aryl, optionally substituted with 6 and R 7 is one or more identical or different substituents R 8 R is independently selected from the group consisting of alkyl, cycloalkyl, and aryl, optionally substituted with 8 is alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3, and R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 1 ~R 9 may be linked together to form one or more saturated or unsaturated carbocyclic rings, or saturated or unsaturated heterocyclic rings, to provide a procatalyst.

[0008] In another aspect, (a) contacting a magnesium-containing compound with a titanium-containing compound; (b) adding to the mixture obtained in step (a) an internal donor, which is a compound of formula (I).

[0009] In another embodiment, (a) the aforementioned olefin polymerization procatalyst; (b) a cocatalyst; (c) an external electron donor.

[0010] In another aspect, there is provided a method for preparing the catalyst system for olefin polymerization, said method comprising contacting the procatalyst for olefin polymerization described above with a cocatalyst and an external electron donor.

[0011] In another aspect, there is provided a process for olefin (co)polymerization comprising contacting at least one olefin monomer with said catalyst system.

[0012] In another aspect, there is provided the use of a compound of formula (I) as an internal electron donor in an olefin polymerization catalyst.

[0013] In another embodiment, the compound of formula (I) The compound is TIFF2025539733000002.tif36169. During the ceremony, R 1 is one or more identical or different substituents R 8 and selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 2 , R 3 , R 4 and R 5 is hydrogen, one or more identical or different substituents R 8 and independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 6 and R 7 is one or more identical or different substituents R 8 R is independently selected from the group consisting of alkyl, cycloalkyl, and aryl, optionally substituted with 8 is alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 1 ~R 9may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings, with the proviso that the compound of formula (I) may be selected from the group consisting of dimethyl (3-bromophenylimino)diacetate, dimethyl 2,2'-(para-methylphenylimino)diacetate, bis(phenylmethyl)2,2'-(2-bromoethylimino)diacetate, di-tert-butyl 2,2'-(2-bromoethylimino)diacetate, di-tert-butyl 2,2'-(2-bromoethylimino)diacetate, di-tert-butyl 2,2'-(benzylimino)diacetate, 2,2'-(benzylimino)diacetate, dibenzyl 2,2'-(2-bromoethylimino)diacetate, di-n-butyl 2,2'-(phenylimino)diacetate, dimethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, dimethyl 2,2'-(bromoethylimino)diacetate, diisopropyl 2,2'-(para-methylphenylimino)diacetate 2,2'-(para-methylphenylimino)diacetate), dimethyl 2,2'-(n-butylimino)diacetate, dimethyl 2,2'-(n-hexylimino)diacetate2'-(n-hexylimino)diacetate), ethyl 2-[(2-ethoxy-2-oxoethyl)-methylamino]-4-methylpentanoate, N-(2-bromoethyl)-N-[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-isoleucine 1,1-dimethylethyl ether ether), N-(2-bromoethyl)-N-[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-phenylalanine 1,1-dimethyl ethyl ether, dimethyl 2,2'-(benzylimino)diacetate, diethyl 2,2'-(benzylimino)diacetate, N-(2-tert-buthoxy-2-oxoethyl)-N-methylglycine ethyl ester ester), diethyl 2,2'-(2,5-dichlorophenylimino)diacetate, diethyl 2,2'-(5-bromo-2-methylphenylimino)diacetate, diethyl 2,2'-(5-iodo-2-methylphenylimino)diacetate, diethyl 2,2'-(5-bromo-4-fluoro-2-methylphenylimino)diacetate, methyl 2-((2-(tert-buthoxy)-2-oxoethyl)(3-chlorophenyl)amino)propanoate, diethyl 2,2'-(n-hexylimino)diacetate, diethyl 2,2'-(n-octylimino)diacetate, di-tert-butyl 2,2'-(n-hexylimino)diacetate 2,2'-(n-hexylimino)diacetate, dimethyl 2,2'-(chloroethylimino)diacetate, 1-methyl-azepan-2,7-dicarboxylic acid dimethyl ester, 1-benzyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, 1-methyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, N-Boc-α-allylproline methyl ester, N-Boc-methanoproline ethyl ester ester), N-benzyl-2,6-dicarbomethoxy-piperidine, 1-para-chlorophenyl-2,5-pyrrolidinedicarboxylic acid diethyl ester5-pyrrolidinedicarboxylic acid diethyl ester, di-tert-butyl 2,2'-diethyl-2,2'-(methylimino)diacetate, di-benzyl 2,2'-diethyl-2,2'-(methylimino)diacetate, di-benzyl 2,2'-dibutyl-2,2'-(methylimino)diacetate, di-tert-butyl 2,2'-diphenyl-2,2'-(methylimino)diacetate The compound is provided as a compound other than 2,2'-diphenyl-2,2'-(methylimino)diacetate. DETAILED DESCRIPTION OF THE INVENTION

[0014] <Detailed Description of the Invention> definition In this disclosure, any reference to the periodic table should be considered a reference to the version of the periodic table approved and released by IUPAC.

[0015] As used herein, the singular terms "a," "an," and "the" can each refer to and include plural references or objects unless specifically defined or stated otherwise, or unless the context clearly indicates otherwise.

[0016] Unless otherwise stated, references to parts or percentages mean parts and percentages by weight.

[0017] As used herein, the expressions "comprise" and "comprising" are synonymous with "include," "including," "contain," or "containing," and do not exclude or preclude the presence of additional components, steps, or operations not recited herein. For the avoidance of doubt, all compositions disclosed herein using the term "containing" may include any additional additives or excipients unless otherwise defined. In contrast, the expression "consisting essentially of" should be understood to exclude additional components, steps, or operations not recited herein from the list below, while permitting the inclusion of additional other items that do not materially affect the operability of the invention. The term "consisting of" should be understood to exclude components, steps, or operations not recited herein or explicitly specified. Unless otherwise specified, the term "or" should be understood to apply to any individual listed element as well as any combination of the listed elements.

[0018] Any numerical range recited herein includes all values ​​from the lower value to the higher value, in increments of one unit, provided that there is a separation of at least two units between any lower value and any higher value. As an example, if an amount of a component, or a value of a composition or physical property, such as the amount of a blend component, softening temperature, melt index, etc., is stated to be between 1 and 100, all individual values, such as 1, 2, 3, etc., and all subranges, such as 1 to 20, 55 to 70, 97 to 100, etc., are intended to be expressly recited herein. For values ​​less than one, one unit is considered to be 0.0001, 0.001, 0.01, or 0.1, as appropriate. These are merely specifically intended examples, and all possible combinations of numerical values ​​between the lowest and highest values ​​recited should be considered expressly stated in this application. In other words, any numerical range recited herein includes any value or subrange within the recited range.

[0019] As used herein, the term "composition" refers to the mixture of materials that initially comprise the composition and to the products that may form as a result of the interreaction and decomposition of each component.

[0020] As used herein, the term "polymer" refers to a macromolecular compound containing repeating structural units called monomers. The term "polymer" includes homopolymers and copolymers.

[0021] As used herein, the term "olefin" refers to an alkene.

[0022] As used herein, the term "olefin-based polymer" refers to a polymer that, in polymerized form, contains a majority weight percent of an olefin, such as ethylene or propylene, based on the total weight of the polymer. Non-limiting examples of olefin-based polymers include ethylene-based polymers and propylene-based polymers.

[0023] As used herein, the term "ethylene-based polymer" refers to a polymer that comprises a majority weight percent polymerized ethylene monomer (based on the total weight of polymerizable monomers), and may optionally include at least one polymerized comonomer.

[0024] As used herein, the term "propylene-based polymer" refers to a polymer that comprises a majority weight percent polymerized propylene monomer (based on the total amount of polymerizable monomers), and may optionally include at least one polymerized comonomer.

[0025] As used herein, the term "polypropylene" refers to a polymer composed of propylene and optionally comonomers.

[0026] As used herein, the term "copolymer" refers to a polymer made from two or more different monomers.

[0027] As used herein, the term "monomer" refers to a chemical compound that can be polymerized.

[0028] As used herein, the terms "hydrocarbyl" or "hydrocarbon" refer to a substituent composed entirely of hydrogen and carbon, which may be straight or branched chain, saturated or unsaturated, cyclic, polycyclic, fused ring or acyclic, and combinations thereof.

[0029] As used herein, the term "alkyl" refers to an alkyl group representing a functional group or side chain consisting of carbon and hydrogen atoms connected by only single bonds. Alkyl groups can be straight or branched, and can be unsubstituted or substituted. Non-limiting examples of suitable alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl (or 2-methylpropyl), and the like. Alkyl groups can have from 1 to 20 carbon atoms.

[0030] As used herein, the term "substituted alkyl" refers to the alkyl described immediately above in which one or more (2, 3, 4, or more) hydrogen atoms attached to any carbon atom of the alkyl have been replaced with another group, such as halogen, aryl, substituted aryl, alkenyl, substituted alkenyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, haloalkyl, hydroxy, amino, phosphido, alkoxy, thio, nitro, other heteroatom-containing groups, and combinations thereof. Suitable substituted alkyls include, for example, benzyl, trifluoromethyl, and the like.

[0031] As used herein, the term "cycloalkyl" refers to a saturated cyclic hydrocarbon group. Cycloalkyl groups can be substituted or unsubstituted. Non-limiting examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. Cycloalkyl groups can have from 3 to 20 carbon atoms.

[0032] As used herein, the term "aryl" refers to an aromatic substituent which may be a single aromatic ring or multiple aromatic rings, which may be fused together, covalently bonded, or linked to each other via a common linking group such as a methylene or ethylene group. The aromatic rings may include phenyl, naphthyl, anthracenyl, and biphenyl, among others. The aryl may have from 6 to 20 carbon atoms.

[0033] As used herein, the term "substituted aryl" refers to an aryl group, as described immediately above, in which one or more (2, 3, 4 or more) hydrogen atoms on the aromatic ring have been replaced with another group. Consequently, the term "substituted aryl group" also includes alkaryl groups in which one or more (2, 3, 4 or more) hydrogen atoms on the aromatic ring have been replaced with alkyl groups, and haloaryl groups in which one or more (2, 3, 4 or more) hydrogen atoms on the aromatic ring have been replaced with halogen atoms.

[0034] As used herein, the term "carbocyclic ring" means a cyclic group composed of carbon atoms. A carbocyclic ring contains exclusively carbon and hydrogen atoms and no atoms of any other type. A carbocyclic ring can be saturated, unsaturated, or aromatic. A carbocyclic ring can have from 3 to 20 carbon atoms.

[0035] As used herein, the term "heterocyclic ring" refers to a cyclic group consisting of carbon atoms and at least one heteroatom. Suitable heteroatoms may include N, O, P, B, S, or Si. The heterocyclic ring may have from 2 to 20 carbon atoms.

[0036] As used herein, the term "Ziegler-Natta catalyst" refers to a solid catalyst compound consisting of Ziegler-Natta catalyst particles containing a transition metal and supported on a metal or semi-metal compound (e.g., a magnesium compound or a silicon compound).

[0037] As used herein, the terms "Ziegler-Natta catalyst particles" or "active catalyst particles" refer to transition metal-containing particles comprising a transition metal halide selected from titanium halide, chromium halide, hafnium halide, zirconium halide, and vanadium halide.

[0038] As used herein, the term "internal donor" or "internal electron donor" refers to a compound capable of donating at least one electron pair to at least one metal present in a procatalyst. As used herein, the term "external donor" or "external electron donor" refers to an electron donor compound used as a reactant in olefin polymerization. An electron donor compound has at least one functional group capable of donating at least one electron pair to a metal atom. The external donor is added to the catalyst system independently of procatalyst formation.

[0039] As used herein, the term "procatalyst" refers to a component of a catalyst composition, which generally includes a solid support containing a transition metal, active catalyst particles, and one or more internal donors.

[0040] As used herein, the term "halide" or "halogen" refers to a halogen selected from the group consisting of fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

[0041] As used herein, the term "heteroatom" refers to an atom other than carbon or hydrogen. However, as used herein, unless otherwise specified, as described below, the phrase "one or more heteroatoms" should be understood to mean one or more of F, Cl, Br, I, N, O, P, B, S, or Si. Thus, the term "heteroatom" also includes halides.

[0042] Unless otherwise specified, the expression that any of the groups R is "independently selected from" or "independently represent" means that for molecules containing several of the same groups R, they can have the same meaning or different meanings. For example, if a compound RM has its R independently selected from ethyl or methyl, then both R groups can be ethyl, both R groups can be methyl, or one R group can be ethyl and the other R group can be methyl.

[0043] The following is a more detailed description of the invention: Any embodiment of one aspect of the invention should be considered applicable to any other aspect of the invention unless otherwise stated.

[0044] According to one aspect of the present invention, there is provided a procatalyst for olefin polymerization comprising a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor that is a compound of formula (I): TIFF2025539733000003.tif34169, wherein R 1 is one or more identical or different substituents R 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 2 , R 3 , R 4 and R 5 is hydrogen, one or more identical or different substituents R 8 R is independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with 6 and R 7 is one or more identical or different substituents R 8 R is independently selected from the group consisting of alkyl, cycloalkyl, and aryl, optionally substituted with 8 is alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR9 3, and R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 1 ~R 9 may be linked together to form one or more (2, 3, 4 or more) saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

[0045] The halogen can be any halogen, for example, fluorine, chlorine, bromine, or iodine.

[0046] In one embodiment of the present invention, the titanium and halogen are present in the procatalyst as components of a compound containing at least one titanium-halogen bond (eg, a titanium halide).

[0047] In one embodiment of the present invention, the titanium-containing compound has the formula: Ti(OR 17 ) n X 4-n and wherein the procatalyst is contained in the form of a compound having the formula: In the formula, R 17 is C1~C 20is an alkyl group; X is a halogen atom; and n is an integer ranging from 0 to 4. Examples of titanium compounds include titanium tetrahalides (or titanium tetrahalides) such as TiCl4, TiBr4, and TiI4; alkoxytitanium trihalides such as Ti(OCH3)C13, Ti(OC2H5)C13, Ti(On-C4H9)C13, Ti(OC2H5)Br3, and Ti(Oi-C4H9)Br3; dialkoxytitanium dihalides such as Ti(OCH3)2Cl2, Ti(OC2H5)2C12, Ti(On-C4H9)2C12, and Ti(OC2H5)2Br2; trialkoxytitanium monohalides such as Ti(OCH3)3Cl, Ti(OC2H5)3Cl, Ti(On-C4H9)3Cl, and Ti(OC2H5)3Br. monohalides); and tetraalkoxytitanium compounds such as Ti(OCH3)4, Ti(OC2H5)4, and Ti(On-C4H9)4. In some embodiments, titanium tetrahalides are advantageously used. The titanium compounds may be used neat or in solution in a hydrocarbon or halogenated hydrocarbon.

[0048] In one embodiment of the present invention, magnesium-containing compounds suitable for preparing the solid procatalyst component include, for example, magnesium compounds in which magnesium is present in the oxidation state +2. In an exemplary embodiment, the magnesium-containing compound is a magnesium halide compound. Specific examples of magnesium-containing compounds include, but are not limited to, magnesium halides (or magnesium halides) such as magnesium chloride, magnesium bromide, magnesium iodide, and magnesium fluoride; alkoxymagnesium halides (or alkoxymagnesium halides) such as methoxymagnesium chloride, ethoxymagnesium chloride, isopropoxymagnesium chloride, butoxymagnesium chloride, and octoxymagnesium chloride; aryloxymagnesium halides (or aryloxymagnesium halides) such as phenoxymagnesium chloride and methylphenoxymagnesium chloride. halides; alkoxymagnesium compounds such as ethoxymagnesium, isopropoxymagnesium, buthoxymagnesium, n-octoxymagnesium, and 2-ethylhexoxymagnesium;Alkyl magnesium halides and aryl magnesium halides (or alkyl and aryl magnesium halides) such as butyl magnesium chloride, amyl magnesium chloride, isoamyl magnesium chloride, hexyl magnesium chloride, phenyl magnesium chloride, tolyl magnesium chloride, and benzyl magnesium chloride; alkylmagnesium compounds such as dibutylmagnesium, butylethylmagnesium, and butyloctylmagnesium; aryloxymagnesium compounds such as phenoxymagnesium and dimethylphenoxymagnesium; and magnesium laurate and magnesium stearate. Magnesium salts of carboxylic acids such as stearate;

[0049] According to a preferred embodiment of the present invention, magnesium halide compounds such as magnesium chloride, alkoxy magnesium chloride, and aryloxymagnesium chloride are used.

[0050] The magnesium-containing supports and titanium halide compounds used in accordance with the present invention are known in the art to be typical components of Ziegler-Natta catalysts. The procatalysts according to the present invention can comprise any of the magnesium-containing supports and compounds known in the art. For example, the preparation of titanium-magnesium-based catalyst compositions supported on various magnesium-containing precursor carriers, such as magnesium halides, (alkyl)magnesium and (aryl)magnesium halides, and (alkoxy)magnesium and (aryloxy)magnesium compounds, for use in the production of polyolefins, particularly polypropylene, can be found in, for example, U.S. Pat. No. 4,978,648, WO 96 / 32,427 A1, WO 01 / 23,441 A1, EP 1,283,222 A1, EP 1,222,214 B1; U.S. Pat. No. 5,077,357; U.S. Pat. No. 5,556,820; U.S. Pat. No. 4,414,132; U.S. Pat. No. 5,106,806; and U.S. Pat. No. 5,077,357, although the method of the present invention is not limited to the teachings of these documents.

[0051] The internal electron donor according to the present invention is of formula (I) The compound is TIFF2025539733000004.tif33170.

[0052] In formula (I), R 1 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0053] In one embodiment, R 1 is alkyl. Preferably, R 1 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 1can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0054] In another embodiment, R 1 is cycloalkyl. Preferably, R 1 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0055] In a further embodiment, R 1 is aryl. Preferably, R 1 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 1 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0056] Furthermore, R 1 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0057] More preferably, R 1 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, and methyldifluorophenyl; aryl selected from the group consisting of haloaryl such as methyldichlorophenyl and methyldibromophenyl; benzocyclopentyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0058] In formula (I), R 2 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0059] In one embodiment, R 2 is hydrogen.

[0060] In another embodiment, R 2 is alkyl. Preferably, R 2 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 2 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0061] In another embodiment, R 2 is cycloalkyl. Preferably, R 2 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0062] In a further embodiment, R 2 is aryl. Preferably, R 2 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 2 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0063] According to the present invention, R 2 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R which may be the same or different. 8 where each R8 is alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) are independently selected from the group consisting of:

[0064] More preferably, R 2 is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, pentyl, or hexyl; alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, and methyldifluorophenyl. , haloaryl such as methyldichlorophenyl, methyldibromophenyl, etc.; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl, etc.; dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 2,6-difluoro-4-ethoxyphenyl, etc.

[0065] In formula (I), R 3 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0066] In one embodiment, R 3 is hydrogen.

[0067] In another embodiment, R 3 is alkyl. Preferably, R 3 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 3 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0068] In another embodiment, R 3 is cycloalkyl. Preferably, R 3 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0069] In a further embodiment, R 3 is aryl. Preferably, R 3 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 3 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0070] According to the present invention, R 3may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0071] More preferably, R 3 is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyl aryl selected from the group consisting of haloaryl such as ethyldichlorophenyl and methyldibromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0072] In formula (I), R 4is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0073] In one embodiment, R 4 is hydrogen.

[0074] In another embodiment, R 4 is alkyl. Preferably, R 4 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 4 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0075] In another embodiment, R 4 is cycloalkyl. Preferably, R 4 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0076] In a further embodiment, R 4 is aryl. Preferably, R 4 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 4is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0077] Furthermore, R 4 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, and the like, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0078] More preferably, R 4is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, and methyldifluorophenyl; and haloaryl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 2,6-difluoro-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0079] In formula (I), R 5 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0080] In one embodiment, R 5 is hydrogen.

[0081] In another embodiment, R 5 is alkyl. Preferably, R 5 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 5can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0082] In another embodiment, R 5 is cycloalkyl. Preferably, R 5 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0083] In a further embodiment, R 5 is aryl. Preferably, R 5 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 5 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0084] Furthermore, R 5 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 are independently selected from the group consisting of: Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl).

[0085] More preferably, R 5 is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, N-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, methylcyclohexyl, methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldiphenyl; and aryl selected from the group consisting of haloaryl such as fluorophenyl, methyldichlorophenyl, and methyldibromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, and (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0086] In formula (I), R 6 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0087] In one embodiment, R 6 is alkyl. Preferably, R 6 C1~C 20Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 6 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0088] In another embodiment, R 6 is cycloalkyl. Preferably, R 6 C 3 ~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0089] In a further embodiment, R 6 is aryl. Preferably, R 6 is C6~C 20 Aryl, more preferably C1-C 10 aryl, most preferably R 6 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0090] Furthermore, R 6 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 are independently selected from the group consisting of: Alkyl, e.g., C1-C 20Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl).

[0091] More preferably, R 6 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyldichlorophenyl, and methylsilyl; haloaryl such as dimethyldibromophenyl, dimethylfluorophenyl, dimethylchlorophenyl, and dimethylbromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, and (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0092] In formula (I), R 7 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0093] In one embodiment, R 7 is alkyl. Preferably, R 7 However, C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 7 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0094] In another embodiment, R 7 is cycloalkyl. Preferably, R 7 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0095] In a further embodiment, R 7 is aryl. Preferably, R 7 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 7 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0096] Furthermore, R 7 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8are independently selected from the group consisting of: Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl).

[0097] More preferably, R 7 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyldichlorophenyl, and methylsilyl; haloaryl such as dimethyldibromophenyl, dimethylfluorophenyl, dimethylchlorophenyl, and dimethylbromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, and (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0098] In one embodiment, R 6 and R 7 is the same.

[0099] In a further embodiment, R in formula (I)1 ~R 9 may be linked together to form one or more (2, 3, 4 or more) saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. 1 and R 4 But R 1 together with the nitrogen atom to which it is attached form a heterocycle, in particular benzopyrrolidine. 2 and R 4 together with the nitrogen atom form a heterocycle, in particular pyrrolidine. 2 and R 3 are linked together to form a carbocyclic ring, in particular cyclohexane. 2 and R 6 is R 6 together with the oxygen atom to which it is attached form a heterocycle. 6 and R 7 is a nitrogen atom and R 6 and R 7 together with the oxygen atom to which it is attached, form a heterocyclic ring, particularly 4-aza-1,7-dioxecane. In one embodiment, the carbocyclic or heterocyclic ring contains 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms. The heteroatoms of the heterocyclic ring may be selected from the group consisting of oxygen, nitrogen, sulfur, boron, silicon, phosphorus, and halogens.

[0100] In one embodiment of the present invention, R 1 , R 6 , and R 7 are each independently C1-C6 alkyl, and R 2 , R 3 , R 4 , and R 5 is hydrogen. In a further embodiment of the invention, R 1 is one or more halogen atoms and / or one or more C1 to C6 alkyl groups and / or one or more C1 to C6 aryl groups and / or one or more C6 to C10 C6-C optionally substituted with aryl groups and / or one or more -O-alkyl groups (wherein alkyl is C1-C6 alkyl). 10 aryl, and R 2 , R 3 , R 4 and R 5 is hydrogen, and R 6 and R 7 Each of R is independently C1-C6 alkyl. 1 is one or more C1 to C6 alkyl groups or one or more C6 to C 10 C3-C optionally substituted with an aryl group 10 is cycloalkyl, and R 2 , R 3 , R 4 , and R 5 is hydrogen, and R 6 and R 7 Each of R is independently C1-C6 alkyl. In a further embodiment, R 1 , R 6 , and R 7 are each independently a C1-C6 alkyl, and R 2 , R 3 , R 4 , and R 5 one of R is aryl optionally substituted with one or more halogen atoms and / or one or more C1-C6 alkyl groups, 2 , R 3 , R 4 , and R 5 is a hydrogen atom. In a further embodiment, R 1 is C1-C6 alkyl, and R 2 , R 3 , R 4 , and R 5 is hydrogen, and R 6 and R 7 each independently represents a C6-C alkyl group optionally substituted with one or more halogen atoms and / or one or more C1-C6 alkyl groups. 10 In a further embodiment, R 1 , R 6 , and R7 are each independently a C1-C6 alkyl, and R 2 and R 5 is hydrogen, and R 3 and R 4 together with the nitrogen atom form a heterocycle containing 4 to 10 carbon atoms. 1 and R 7 are each independently C1-C6 alkyl, and R 3 , R 4 and R 5 is hydrogen, and R 2 and R 6 together with the carboxylic carbon atom and the oxygen atom form a heterocycle containing 4 to 10 carbon atoms. 1 , R 6 , and R 7 are each independently a C1-C6 alkyl, and R 2 and R 3 together with the carbon atom to which they are attached form a carbocyclic ring containing 3 to 10 carbon atoms, and R 4 and R 5 Each of R is hydrogen. 1 C6-C optionally substituted with one or more halogen atoms and / or one or more C1-C6 alkyl groups and / or one or more -O-alkyl groups (wherein alkyl is C1-C6 alkyl). 10 aryl, and R 2 , R 3 , R 4 , and R 5 is hydrogen, and R 6 and R 7 are linked together to form a heterocycle containing 6 to 10 carbon atoms. 1 , R 6 , and R 7 each independently represents a C6-C alkyl group optionally substituted with one or more halogen atoms and / or one or more C1-C6 alkyl groups and / or one or more -O-alkyl groups (wherein alkyl is C1-C6 alkyl). 10aryl, and R 2 , R 3 , R 4 , and R 5 Each of R is hydrogen. 1 and R 2 together with the nitrogen atom, one or more C1 to C6 alkyl groups or one or more C6 to C 10 R forms a heterocyclic ring containing 3 to 10 carbon atoms, which may be substituted with an aryl group; 3 , R 4 , and R 5 is hydrogen, and R 6 and R 7 Each of R is independently C1-C6 alkyl. 1 SiR 9 C6~C substituted with 3 10 aryl, where each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 aryl, and R 2 , R 3 , R 4 , and R 5 is hydrogen, and R 6 and R 7 Each of is independently C1-C6 alkyl. In a further embodiment, R 1 is C1-C6 alkyl, and R 2 , R 3 , R 4 , and R 5 is hydrogen, and R 6 and R 7 each independently represents a group SiR 9 3, wherein each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 In a further embodiment, R 1 However, the group SiR 9 3, wherein each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 aryl, and R 2 , R 3 , R4 , and R 5 is hydrogen, and R 6 and R 7 Each of is independently C1 to C6 alkyl.

[0101] In one embodiment of the present invention, the compound of formula (I) is TIFF2025539733000005.tif29169 compound, During the ceremony R 10 ,R 11 and R 12 is one or more (2, 3, 4 or more) substituents R which may be the same or different 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, each R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 (where R 9 are independently selected from the group consisting of alkyl, cycloalkyl, and aryl; and R 10 ~R 12 may be linked together to form one or more (2, 3, 4, or more) saturated or unsaturated carbocyclic rings, or saturated or unsaturated heterocyclic rings.

[0102] In formula (II), R 10 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0103] In one embodiment, R 10 is alkyl. Preferably, R 10 C1~C 20 Linear or branched alkyl, more preferably C1-C 10It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 10 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0104] In another embodiment, R 10 is cycloalkyl. Preferably, R 10 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0105] In a further embodiment, R 10 is aryl. Preferably, R 10 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 10 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0106] Furthermore, R 10 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0107] More preferably, R 10 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methylsilyl, and methylsilyl; and aryl selected from the group consisting of haloaryl such as methyldichlorophenyl and methyldibromophenyl, (alkylsilyl)phenyl such as benzocyclopentyl, (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0108] In formula (II), R 11 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0109] In one embodiment, R 11 is alkyl. Preferably, R11 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 11 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0110] In another embodiment, R 11 is cycloalkyl. Preferably, R 11 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0111] In a further embodiment, R 11 is aryl. Preferably, R 11 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 11 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0112] Furthermore, R 11 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0113] Furthermore, R 11 is preferably an alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; a cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; an alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl; difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, and methyldichlorophenyl. , methyldibromophenyl, dimethylfluorophenyl, dimethylchlorophenyl, dimethylbromophenyl, and the like; (alkylsilyl)phenyl, such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl, such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 2,6-difluoro-4-ethoxyphenyl, and the like.

[0114] In formula (II), R 12 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0115] In one embodiment, R 12 is alkyl. Preferably, R 12 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 12 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0116] In another embodiment, R 12 is cycloalkyl. Preferably, R 12 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0117] In a further embodiment, R 12 is aryl. Preferably, R 12 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 12 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0118] Furthermore, R 12 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0119] Further, preferably, R 12 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl; difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyldichlorophenyl, and methylsilyl; haloaryl such as ethyldibromophenyl, dimethylfluorophenyl, dimethylchlorophenyl, dimethylbromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 2,6-difluoro-4-ethoxyphenyl.

[0120] In one embodiment, R 11 and R 12 is the same.

[0121] In a further embodiment, R in formula (II) 10 ~R 12 may be linked together to form one or more (2, 3, 4, or more) saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. 11 and R 12 is a nitrogen atom and R 11 and R 12 together with the oxygen atom to which it is attached to form a heterocyclic ring, particularly 4-aza-1,7-dioxecane. In one embodiment, the carbocyclic or heterocyclic ring has 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms. The heteroatoms of the heterocyclic ring may be selected from the group consisting of oxygen, nitrogen, sulfur, boron, silicon, phosphorus, and halogens.

[0122] In one embodiment of the present invention, R 10 , R 11 , and R 12 Each of is independently C1-C6 alkyl. In a further embodiment of the invention, R 10 is one or more halogen atoms and / or one or more C1 to C6 alkyl groups and / or one or more C6 to C 10 C6-C optionally substituted with aryl groups and / or one or more -O-alkyl groups, where alkyl is C1-C6 alkyl. 10 aryl, and R 11 and R 12 Each of R is independently C1-C6 alkyl. 10 is one or more C1 to C6 alkyl groups or one or more C6 to C 10 C3-C optionally substituted with an aryl group 10 is cycloalkyl, and R 11 and R 12 Each of is independently C1-C6 alkyl. In a further embodiment, R 10 is C1-C6 alkyl, and R 11 and R 12 each independently represents a C6-C group optionally substituted with one or more halogen atoms and / or one or more C1-C6 alkyl groups.10 In a further embodiment, R 10 is a C6-C alkyl group optionally substituted with one or more halogen atoms and / or one or more C1-C6 alkyl groups and / or one or more -O-alkyl groups (wherein alkyl is C1-C6 alkyl). 10 aryl, and R 11 and R 12 together form a heterocyclic ring containing 6 to 10 carbon atoms.

[0123] In a further embodiment, R 10 , R 11 and R 12 each independently represents a C-C alkyl group optionally substituted with one or more halogen atoms and / or one or more C-C alkyl groups and / or one or more -O-alkyl groups, where alkyl is C-C alkyl. 10 In a further embodiment, R 10 is the group SiR 9 C6~C substituted with 3 10 aryl, where each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 aryl, and R 11 and R 12 Each of is independently C1-C6 alkyl. In a further embodiment, R 10 is C1-C6 alkyl, and R 11 and R 12 each independently represents a group SiR 9 3, wherein each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 In a further embodiment, R 10 is the group SiR 9 3, wherein each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 aryl, and R 11 and R 12 Each of is independently a C1-C6 alkyl.

[0124] In one embodiment of the present invention, the compound of formula (I) is represented by formula (III) The compound is TIFF2025539733000006.tif51169. During the ceremony R 13 and R 14 is independent, one or more (2, 3, 4 or more) substituents R, which may be the same or different; 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 is independent, Alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 (where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; and R 13 and R 14 may be linked together to form one or more (2, 3, 4 or more) saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings, R 15 and R 16 is hydrogen, alkyl or cycloalkyl, optionally substituted aryl, halogen, -SiR 9 3 (where R 9 are independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 28 is selected from the group consisting of hydrogen, -O-alkyl.

[0125] In formula (III), R 13 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0126] In one embodiment, R 13 is alkyl. Preferably, R 13 However, C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 13 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0127] In another embodiment, R 13 is cycloalkyl. Preferably, R 13 But C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0128] In a further embodiment, R 13 is aryl. Preferably, R 13 C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 13 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0129] Furthermore, R 13 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0130] More preferably, R 13 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyldichlorophenyl, and methyldibromophenyl; haloaryl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 2,6-difluoro-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0131] In formula (III), R 14 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8may be substituted with.

[0132] In one embodiment, R 14 is alkyl. Preferably, R 14 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 14 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0133] In another embodiment, R 14 is cycloalkyl. Preferably, R 14 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0134] In a further embodiment, R 14 is aryl. Preferably, R 14 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 14 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0135] Furthermore, R 14 may be unsubstituted or may be one or more (2, 3, 4 or more) substituents R which may be the same or different;8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (two, three, four or more) halogen atoms selected from chlorine, fluorine, bromine or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0136] More preferably, R 14 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyldichlorophenyl, and methyl haloaryl such as dimethyldibromophenyl, dimethylfluorophenyl, dimethylchlorophenyl, and dimethylbromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, and (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0137] In one embodiment, R 13 and R 14is the same.

[0138] In formula (III), R 15 is selected from the group consisting of hydrogen, halogen, alkyl, cycloalkyl, and optionally substituted aryl.

[0139] In one embodiment, R 15 is hydrogen.

[0140] In another embodiment, R 15 is a halogen. In particular, R 15 may be selected from the group comprising fluorine, chlorine, iodine, and bromine.

[0141] In a further embodiment, R 15 is alkyl. Preferably, R 15 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 15 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

[0142] In another embodiment, R 15 is cycloalkyl. Preferably, R 15 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, especially cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl.

[0143] In a further embodiment, R 15 is aryl. Preferably, R 15 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 15is phenyl. Further, the aryl may be substituted with one or more (2, 3, 4 or more) alkyl substituents containing 1 to 20, preferably 1 to 10, more preferably 1 to 6 carbon atoms.

[0144] More preferably, R 15 is hydrogen; a halogen selected from the group consisting of fluorine, chlorine, iodine, and bromine; an alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; a cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; and an aryl selected from the group consisting of phenyl and alkylphenyl, such as methylphenyl or ethylphenyl.

[0145] In formula (III), R 16 is selected from the group consisting of hydrogen, halogen, alkyl, cycloalkyl, and optionally substituted aryl.

[0146] In one embodiment, R 16 is hydrogen.

[0147] In another embodiment, R 16 is a halogen. In particular, R 16 may be selected from the group comprising fluorine, chlorine, iodine, and bromine.

[0148] In a further embodiment, R 16 is alkyl. Preferably, R 16 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 16 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

[0149] In another embodiment, R 16 is cycloalkyl. Preferably, R 16 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, especially cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl.

[0150] In a further embodiment, R 16 is aryl. Preferably, R 16 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 16 is phenyl. Furthermore, the aryl may be substituted with one or more (2, 3, 4 or more) alkyl substituents containing 1 to 20, preferably 1 to 10, more preferably 1 to 6 carbon atoms. In particular, R 16 can be methylphenyl.

[0151] More preferably, R 16 is hydrogen; a halogen selected from the group consisting of fluorine, chlorine, iodine, and bromine; an alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; a cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; and an aryl selected from the group consisting of phenyl and alkylphenyl, such as methylphenyl or ethylphenyl.

[0152] In formula (III), R 28 is selected from the group consisting of hydrogen and -O-alkyl.

[0153] In one embodiment, R 28 is hydrogen.

[0154] In another embodiment, R 28is -O-alkyl, where alkyl is C1-C 20 Straight or branched chain alkyl, more preferably C1-C 10 It is a straight or branched chain alkyl, for example a C1-C6 straight or branched chain alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl.

[0155] In one embodiment of the present invention, R 13 , R 14 , and R 16 are each independently a C1-C6 alkyl, and R 15 and R 28 Each of R is hydrogen. 13 , R 14 , R 15 , and R 16 are each independently a C1-C6 alkyl, and R 28 is hydrogen. In a further embodiment of the present invention, R 13 and R 14 are each independently C1-C6 alkyl, and R 15 , R 16 and R 28 Each of R is hydrogen. 13 and R 14 are each independently C1-C6 alkyl, and R 15 and R 16 Each of R is a halogen, 28 is hydrogen. In a further embodiment of the present invention, R 13 and R 14 are each independently C1-C6 alkyl, and R 15 and R 16 each of which is a halogen, and R 28 is hydrogen. In a further embodiment of the present invention, R 13 , R 14 and R 16 are each independently a C1-C6 alkyl, and R 15 is C6~C 10 aryl, and R 28is hydrogen. In a further embodiment of the present invention, R 15 and R 16 are each independently C1-C6 alkyl, and R 28 is hydrogen and R 13 and R 14 together form a heterocycle containing 6 to 10 carbon atoms. 13 and R 14 are each independently C1-C6 alkyl, and R 15 and R 16 One of the groups is SiR 9 3, where each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 aryl, and R 15 and R 16 and the other is a hydrogen atom. 13 and R 14 are each independently C1-C6 alkyl, and R 15 and R 16 each of which is a halogen, and R 28 is -O-alkyl, where alkyl is a C1 to C6 straight chain or branched alkyl.

[0156] In one embodiment of the present invention, the compound of formula (I) is represented by formula (IV) TIFF2025539733000007.tif36169 compound, During the ceremony R 18 and R 19 are independently one or more (2, 3, 4 or more) substituents R which may be the same or different. 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 20 , R 21 , R 22 and R 23 are independently hydrogen, one or more (2, 3, 4 or more) substituents R which may be the same or different. 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 are independently alkyl, cycloalkyl, optionally substituted aryl, halogen, or -O-alkyl; -SiR 9 3, (where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; is selected from the group consisting of In the formula, R 18 ~R 23 may be linked together to form one or more (2, 3, 4 or more) saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

[0157] In formula (IV), R 18 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0158] In one embodiment, R 18 is alkyl. Preferably, R 18 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 18 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0159] In another embodiment, R 18 is cycloalkyl. Preferably, R 18 C3~C 20 Cycloalkyl, more preferably C3-C 10Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0160] In a further embodiment, R 18 is aryl. Preferably, R 18 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 18 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0161] Furthermore, R 18 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine or iodine, C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0162] More preferably, R 18alkylsilylalkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, or hexyl, (trimethylsilyl)methyl, or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl; difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyldichlorophenyl, methyldibromophenyl, di and alkyl selected from the group consisting of haloaryl such as methylfluorophenyl, dimethylchlorophenyl, and dimethylbromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0163] In formula (IV), R 19 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0164] In one embodiment, R 19 is alkyl. Preferably, R 19 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 19can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0165] In another embodiment, R 19 is cycloalkyl. Preferably, R 19 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0166] In a further embodiment, R 19 is aryl. Preferably, R 19 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 19 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0167] Furthermore, R 19 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0168] More preferably, R 19 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, methyldifluorophenyl, methyldichlorophenyl, and methylsilyl; haloaryl such as dimethyldibromophenyl, dimethylfluorophenyl, dimethylchlorophenyl, and dimethylbromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, and (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0169] In one embodiment, R 18 and R 19 is the same.

[0170] In formula (IV), R 20is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0171] In one embodiment, R 20 is hydrogen.

[0172] In another embodiment, R 20 is alkyl. Preferably, R 20 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 20 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0173] In another embodiment, R 20 is cycloalkyl. Preferably, R 20 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0174] In a further embodiment, R 20 is aryl. Preferably, R 20 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 20is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0175] Furthermore, R 20 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0176] More preferably, R 20is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl; difluorophenyl, dichlorophenyl, dibromophenyl, and methyldifluorophenyl; haloaryl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 2,6-difluoro-4-ethoxyphenyl, and the like; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0177] In formula (IV), R 21 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0178] In one embodiment, R 21 is hydrogen.

[0179] In another embodiment, R 21 is alkyl. Preferably, R 21 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example a C1-C6 straight chain or branched alkyl. In particular, R 21can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0180] In another embodiment, R 21 is cycloalkyl. Preferably, R 21 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0181] In a further embodiment, R 21 is aryl. Preferably, R 21 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 21 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0182] Furthermore, R 21 may be unsubstituted or may be one or more (2, 3, 4 or more) substituents R which may be the same or different; 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (two, three, four or more) halogen atoms selected from chlorine, fluorine, bromine or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0183] More preferably, R 21 is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl; difluorophenyl, dichlorophenyl, dibromophenyl, and methyldifluorophenyl; haloaryl such as methylsilyl, methyldichlorophenyl, and methyldibromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; and dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0184] In formula (IV), R 22 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8 may be substituted with.

[0185] In one embodiment, R 22 is hydrogen.

[0186] In another embodiment, R 22 is alkyl. Preferably, R 22 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 22 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0187] In another embodiment, R 22 is cycloalkyl. Preferably, R 22 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0188] In a further embodiment, R 22 is aryl. Preferably, R 22 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 22 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0189] Furthermore, R 22 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, more preferably with cycloalkyl such as C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0190] More preferably, R 22 is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and methylcyclohexyl; alkylphenyl such as phenyl, dimethylphenyl, diethylphenyl, isopropylphenyl, and diisopropylphenyl; difluorophenyl, dichlorophenyl, dibromophenyl, and methyldifluorophenyl; haloaryl such as phenyl, methyldichlorophenyl, methyldibromophenyl; (alkylsilyl)phenyl such as (triethylsilyl)phenyl, (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, and 2,6-difluoro-4-ethoxyphenyl.

[0191] In formula (IV), R 23 is one or more (2, 3, 4 or more) substituents R, which may be the same or different, selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl; 8may be substituted with.

[0192] In one embodiment, R 23 is hydrogen.

[0193] In another embodiment, R 23 is alkyl. Preferably, R 23 C1~C 20 Linear or branched alkyl, more preferably C1-C 10 It is a straight chain or branched alkyl, for example, a C1-C6 straight chain or branched alkyl. In particular, R 23 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. Additionally, the alkyl can have one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0194] In another embodiment, R 23 is cycloalkyl. Preferably, R 23 C3~C 20 Cycloalkyl, more preferably C3-C 10 Cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl. Furthermore, said cycloalkyl may contain one or more (2, 3, 4 or more) substituents R 8 may be substituted with.

[0195] In a further embodiment, R 23 is aryl. Preferably, R 23 is C6~C 20 Aryl, more preferably C6-C 10 aryl, most preferably R 23 is phenyl. Furthermore, the aryl may contain one or more (2, 3, 4, or more) substituents R 8 may be substituted with.

[0196] Furthermore, R23 may be unsubstituted or may contain one or more (2, 3, 4 or more) substituents R, which may be the same or different. 8 where each R 8 is independent, Alkyl, e.g., C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; Cycloalkyl, e.g., C3-C 20 Cycloalkyl, more preferably C3-C 10 cycloalkyl, even more preferably C3-C6 cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or methylcyclohexyl; Optionally substituted aryl, for example C-C 20 Aryl, more preferably C6-C 10 aryl, most preferably phenyl, wherein the aryl is preferably one or more (2, 3, 4 or more) halogen atoms selected from chlorine, fluorine, bromine, or iodine; C1-C 20 Alkyl, preferably C1-C 10 alkyl, more preferably C1 to C6 alkyl, or C3 to C 20 Cycloalkyl, preferably C3-C 10 aryl optionally substituted with cycloalkyl, such as cycloalkyl, more preferably C3-C6 cycloalkyl; a halogen, preferably fluorine, chlorine, bromine or iodine; -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, more preferably C1-C 10 linear or branched alkyl, for example, C1-C6 linear or branched alkyl, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; -SiR 9 3 (in the formula, each R 9 are independently alkyl, cycloalkyl, and aryl, preferably C1-C 20 Straight or branched alkyl, C3-C 20 Cycloalkyl or C6-C 20 Aryl, more preferably C1-C 10 Straight or branched alkyl, C3-C 10 Cycloalkyl or C6-C 10 aryl, for example, selected from the group consisting of C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, or phenyl) is selected from the group consisting of:

[0197] More preferably, R 23 is hydrogen; alkyl selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, alkylsilylalkyl such as (trimethylsilyl)methyl or (triethylsilyl)methyl; cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl; alkylphenyl such as phenyl, dimethylchlorophenyl, diethylphenyl, isopropylphenyl, diisopropylphenyl; difluorophenyl, dichlorophenyl, dibromophenyl, methyl haloaryl such as methyldifluorophenyl, methyldichlorophenyl, methyldibromophenyl; (alkylsilyl)phenyl such as (trimethylsilyl)phenyl, (dimethylphenylsilyl)phenyl, or (diethylphenylsilyl)phenyl; dihaloalkoxyphenyl such as 2,6-dichloro-4-methoxyphenyl, 2,6-dibromo-4-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 2,6-difluoro-4-ethoxyphenyl.

[0198] In a further embodiment, R in formula (IV) 18 ~R23 may be linked together to form one or more (2, 3, 4, or more) saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. 20 and R 22 together with the nitrogen atom form a heterocycle, in particular pyrrolidine. 20 and R 21 are linked to form a carbocyclic ring, particularly cyclohexane. 20 and R 18 is R 18 together with the oxygen atom to which it is attached form a heterocycle, particularly tetrahydrofuran. In one embodiment, the carbocycle or heterocycle contains 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms. The heteroatoms of the heterocycle may be selected from the group consisting of oxygen, nitrogen, sulfur, boron, silicon, phosphorus, and halogens.

[0199] In one embodiment of the present invention, R 18 and R 19 are each independently C1-C6 alkyl, and R 20 , R 21 , R 22 and R 23 Each of R is hydrogen. 18 and R 19 are each independently C1-C6 alkyl, and R 20 , R 21 , R 22 and R 23 is aryl optionally substituted with one or more halogen atoms and / or one or more C1-C6 alkyl groups, and 20 , R 21 , R 22 and R 23 is a hydrogen atom. In a further embodiment, R 18 and R 19 are each independently C1-C6 alkyl, and R 20 and R 23 is hydrogen, and R 21 and R22 together with the nitrogen atom form a heterocycle containing 4 to 10 carbon atoms. 19 is C1-C6 alkyl, and R 21 , R 22 , and R 23 is hydrogen, and R 18 and R 20 together with the carboxylic acid carbon atom and the oxygen atom form a heterocyclic ring containing 4 to 10 carbon atoms. 18 and R 19 are each independently C1-C6 alkyl, and R 20 and R 21 together with the carbon atom to which they are attached form a carbocyclic ring containing 3 to 10 carbon atoms, and R 22 and R 23 Each of R is hydrogen. 18 and R 19 each independently represents a group SiR 9 3, wherein each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 aryl, and R 20 , R 21 , R 22 , and R 23 Each of R is hydrogen. 18 and R 19 Each of the groups SiR 9 C6~C substituted with 3 10 aryl, where each R 9 are independently C1 to C6 alkyl and / or C6 to C 10 aryl, and R 20 , R 21 , R 22 , and R 23 Each of is hydrogen.

[0200] Specific examples of compounds having formula (I) suitable for use as internal donors include diethyl 2,2'-(isopropylimino)diacetate, diethyl 2,2'-(2,6-diethylphenylimino)diacetate, diethyl 2,2'-(2,6-diisopropylphenylimino)diacetate, diethyl 2,2'-(2-isopropylphenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(2,6-difluorophenylimino)diacetate, 2,2'-(2,6-difluorophenylimino)diacetate, diethyl 2,2'-(2,6-dibromo-4-methylphenylimino)diacetate, diethyl 2,2'-(2,6-dichlorophenylimino)diacetate, diethyl 2,2'-(4-bromo-2,6-diethylphenylimino)diacetate, diethyl 2,2'-(2,6-dibromo-4-methoxyphenylimino)diacetate 2,2'-(2,6-dibromo-4-methoxyphenylimino)diacetate), diethyl 2,2'-(2-methylcyclohexylimino)diacetate, di-n-butyl (2,6-di-tert-butylphenylimino)diacetate6-di-tert-butylphenylimino)diacetate), diethyl 2,2'-(2-para-methylphenyl-4,6-dimethylphenylimino)diacetate, diethyl 2,2'-(N-indan-1-ylimino)diacetate, diethyl 2-(3,5-dimethylphenyl)-2,2'-(isopropylimino)diacetate, ethyl 2-(2-(ethoxycarbonyl)indolin-1-yl)acetate -yl)acetate), bis(3,5-dimethyl-4-chlorophenyl) 2,2'-(2,6-diethylphenylimino)diacetate, diethyl (2S,5S)-(N-isopropyl)-pyrrolidine-2,5-diformate, N-isopropyl-N-(2-ethoxy-2-ketoethyl)-alpha-amino-gamma-butyrolactone, ethyl alpha-(N-isopropyl-N-(1-(ethoxycarbonyl)cyclohexyl)amino)acetate alpha-(N-isopropyl-N-(1- (ethoxycarbonyl)cyclohexyl)amino)acetate), 4-(2,6-diethylphenyl)-2,6-dioxo-4-aza-l,7-dioxecane, diethyl 2,2'-(para-(triethylsilyl)phenylimino)diacetate, diethyl 2,2'-(meta-(trimethylsilyl)phenylimino)diacetate, diethyl 2,2'-(ortho-(trimethylsilyl)phenylimino)diacetate, diethyl 2,2'-((dimethylphenylsilyl)ethylimino)diacetate), bis(trimethylsilylmethyl) 2,2'-(isopropylimino)diacetate (isopropylimino)diacetate).

[0201] Compounds of formula (I) can be obtained by reacting an N-alkyl- or N-arylamine with an alpha-halogen-substituted carboxylic acid ester in the presence of a base and (optionally) a salt additive, suitably iodide, in a solvent. The reaction can be carried out either at elevated temperature or at room temperature.

[0202] The synthesis can be carried out according to a one-step route by reacting two equivalents of an alpha-halo carboxylic acid ester, in which case the product formed is a symmetrically substituted iminodiacetate. TIFF2025539733000008.tif33169

[0203] Alternatively, the target compound can be prepared via two reaction steps by reacting only one equivalent of an alpha-halocarboxylic acid ester in each step; suitably, this synthetic route allows the preparation of asymmetrically substituted iminodiacetates, provided that different alpha-halogen-substituted carboxylic acid esters are used in the different steps. First step: TIFF2025539733000009.tif38169 Second process: TIFF2025539733000010.tif33169

[0204] Non-limiting examples of suitable compounds that can be used as bases in the present invention include potassium carbonate, sodium carbonate, potassium bicarbonate, triethylamine, diisopropylethylamine, etc. In some cases, an excess of the starting N-alkyl- or N-arylamine can be used as the base.

[0205] Non-limiting examples of suitable solvents include acetone, acetonitrile, dimethylformamide, tetrahydrofuran, and the like.

[0206] Non-limiting examples of suitable salt additives, ie, iodides (salts of hydroiodic acid), include sodium iodide, potassium iodide, tetramethylammonium iodide, and the like.

[0207] In some cases, the starting compound may be an N-alkyl- or N-arylamine salt, optionally in combination with an excess of base.

[0208] Also, the compound of formula (I) is -SiR 9 When the target compound contains a substituent represented by the group 3, the target compound can be prepared according to the following scheme: It can be synthesized according to TIFF2025539733000011.tif93142.

[0209] The above route can be used to prepare the following compounds: It can be used to prepare TIFF2025539733000012.tif54132.

[0210] According to one embodiment of the present invention, there is provided a procatalyst for olefin polymerization that contains a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor that is a compound of formula (I). In particular, there is provided a procatalyst for olefin polymerization that contains a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor that is a compound of formula (II), a compound of formula (III), or a compound of formula (IV).

[0211] According to a further aspect of the present invention, there is provided a method for preparing an olefin polymerization procatalyst containing a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor that is a compound of Formula (I). Specifically, the present invention relates to a method for preparing an olefin polymerization procatalyst containing a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor that is a compound of Formula (II), Formula (III), or Formula (IV). In one embodiment, the method comprises the steps of: (a) contacting a magnesium-containing compound, preferably MgCl, with a titanium-containing compound, preferably TiCl; and (b) adding the internal donor, which is a compound of Formula (I), to the resulting mixture. In one embodiment, the magnesium-containing compound to be combined with TiCl in step (a) is present in a mixture with phthalic anhydride, epichlorhydrin, tributyl phosphate (or tributyl phosphate), and toluene, and the mixture is cooled to −30° C. before being combined with TiCl. In a further embodiment, combining MgCl and TiCl in step (a) is carried out by dropwise addition of TiCl while maintaining the temperature of the mixture below -25°C. In a further embodiment, the mixture of step (a) is heated to 85°C prior to the addition of the internal donor. In one embodiment, the addition of the internal donor to the mixture obtained in step (a) is carried out as a two-stage operation. The suspension obtained in step (b) is filtered, washed, and dried to obtain the target particulate procatalyst for olefin polymerization.

[0212] According to another aspect of the present invention, there is provided a catalyst system for the polymerization of olefins, the catalyst system comprising: (a) a procatalyst for olefin polymerization as described above; and (b) a cocatalyst; and (c) external electron donor Includes:

[0213] The catalyst system of the present invention may include a cocatalyst. The term "cocatalyst," as used herein, has its general meaning known to those skilled in the art of Ziegler-Natta catalysis and refers to a substance capable of converting a procatalyst into an active polymerization catalyst. Cocatalysts of the present invention are typically organometallic compounds containing a metal from Groups 1, 2, 12, or 13 of the Periodic Table. The cocatalyst of the present invention may be any compound known in the art to be used as a "cocatalyst."

[0214] The co-catalyst may be at least one organoaluminum compound. According to the present invention, any compound having at least one aluminum-carbon bond in the molecule may be used. Examples of organoaluminum compounds include those of the formula AlR 24 m X 3-m In particular, the molecule 24 are independently selected from hydrocarbon groups generally having 1 to 20 carbon atoms, X is a halogen atom, and n is greater than 0 and less than or equal to 3.

[0215] Specific examples of organoaluminum compounds suitable for use as cocatalysts include, but are not limited to, various trialkylaluminums such as triethylaluminum, triisobutylaluminum, tri-n-butylaluminum, tri-n-hexylaluminum, and tri-n-octylaluminum; various trialkenylaluminums such as triisoprenylaluminum; dialkylaluminum halides such as diethylaluminum chloride, dibutylaluminum chloride, and diethylaluminum bromide; alkylaluminum sesquihalides such as ethylaluminum sesquichloride, butylaluminum sesquichloride, and ethylaluminum sesquibromide; alkylaluminum dihalides such as n-propylaluminum dichloride, n-propylaluminum dichloride, and butylaluminum dibromide; dialkylaluminum hydrides such as diethylaluminum hydride and dibutylaluminum hydride; and Other partially hydrogenated alkylaluminums include ethylaluminum dihydride and n-propylaluminum dihydride.

[0216] The organoaluminum compound is present in the catalyst system in an amount such that the molar ratio of aluminum to titanium (present in the procatalyst) is from about 0.1 to about 2000. In another embodiment, the molar ratio of aluminum to titanium in the catalyst system is from about 5 to about 1000. In another embodiment, the molar ratio of aluminum to titanium in the catalyst system is from about 10 to about 700. In a further embodiment, the molar ratio of aluminum to titanium in the catalyst system is from about 25 to about 400.

[0217] The external electron donor used in the catalyst system can include any compound known in the art as an external electron donor. Examples of preferred external donors include silicon compounds, ethers, esters, amines, and heterocyclic compounds.

[0218] Another class of preferred external donor compounds is represented by the formula (R 25 ) a (R 26 ) b Si(OR 27 ) c (wherein a and b are integers of 0 to 2, c is an integer of 1 to 4, and the sum (a+b+c) is 4; R 25 , R 26 , and R 27 is a radical having 1 to 18 carbon atoms which may contain heteroatoms). Particularly preferred are silicon compounds in which a is 1, b is 1, c is 2, and R 25 and R 26 at least one of R is selected from a branched alkyl, cycloalkyl, or aryl group having 3 to 10 carbon atoms, which may contain heteroatoms; 27 C1~C 10Silicon compounds having alkyl groups, especially methyl. Examples of such preferred silicon compounds include methylcyclohexyldimethoxysilane, diphenyldimethoxysilane, methyl-t-butyldimethoxysilane, dicyclopentyldimethoxysilane, diisopropyldimethoxysilane, (2-ethylpiperidinyl)t-butyldimethoxysilane, (2-ethylpiperidinyl)t-hexyldimethoxysilane, (3,3,3-trifluoro-n-propyl)(2-ethylpiperidinyl)dimethoxysilane, and the like. silane, methyl(3,3,3-trifluoro-n-propyl)dimethoxysilane, and N,N-diethylaminotriethoxysilane. Furthermore, when a is 0, c is 3, and R 26 is a branched alkyl or cycloalkyl group which may contain heteroatoms, and R 27 Also preferred are silicon compounds in which R is methyl. Examples of such preferred silicon compounds are cyclohexyltrimethoxysilane, t-butyltrimethoxysilane, and hexyltrimethoxysilane.

[0219] The external electron donor is used in an amount such as to give a molar ratio between the cocatalyst, which is preferably an organoaluminum compound, and said external electron donor of 0.1-500, preferably 1-300, more preferably 3-100.

[0220] According to a further aspect of the present invention, there is provided a process for the preparation of a catalyst system for the polymerization of olefins, the process comprising contacting a procatalyst as described above with a cocatalyst as described above, and an external donor as described above.

[0221] According to another aspect of the present invention, there is provided a process for olefin (co)polymerization, comprising contacting at least one olefin monomer with the above-described catalyst system. In one embodiment of the present invention, the olefin is an alpha-olefin. Preferably, the olefin contains 2 to 40 carbon atoms, more preferably 2 to 12 carbon atoms. More specifically, the olefin may be selected from ethylene, propylene, 1-butene, 4-methyl-1-pentene, 1-hexene, and 1-octene.

[0222] The process for olefin (co)polymerization may be carried out according to any polymerization technique known in the art, such as slurry polymerization in an inert hydrocarbon diluent or bulk polymerization using a liquid monomer (e.g., propylene) as the reaction medium. Furthermore, the process for olefin (co)polymerization may be carried out in the gas phase in a fluidized bed reactor or a stirred bed reactor.

[0223] According to the present invention, the (co)polymerization temperature is generally in the range of 20 to 120°C, preferably 40 to 80°C. In the case of gas-phase (co)polymerization, the operating pressure is generally in the range of 0.5 to 10 MPa, preferably 1 to 5 MPa. In the case of bulk (co)polymerization, the operating pressure is usually in the range of 1 to 6 MPa, preferably 1.5 to 4 MPa. The molecular weight of the resulting polymer can be controlled by adding hydrogen or other compounds known to be used as chain-transfer agents.

[0224] The (co)polymerization process may include a prepolymerization step. Said step may be carried out by any method known in the art. In one embodiment, prepolymerization involves contacting a small amount of olefin with the catalyst system after the procatalyst has been contacted with a cocatalyst and an external electron donor. The resulting preactivated catalyst stream is then introduced into the polymerization reaction zone and contacted with the remainder of the olefin monomer to be polymerized, and optionally one or more external electron donors. Prepolymerization results in the procatalyst combined with the cocatalyst and external electron donor, and this combination is dispersed in the matrix of the formant polymer. Optionally, an additional amount of external electron donor may be added.

[0225] According to a further aspect of the present invention, there is provided the use of a compound of formula (I) as an internal electron donor in a catalyst for olefin polymerization. More particularly, there is provided the use of a compound of formula (II), a compound of formula (III), or a compound of formula (IV) as an internal electron donor in a catalyst for olefin polymerization.

[0226] According to another aspect of the present invention, a compound of formula (I) TIFF2025539733000013.tif3674 (in the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7is as defined above), In particular, according to the present invention, TIFF2025539733000014.tif2864(in the formula, R 10 , R 11 , and R 12 is as defined above), or formula (III) TIFF2025539733000015.tif4975(in the formula, R 13 , R 14 , R 15 , R 16 and R 28 is as defined above), or formula (IV) TIFF2025539733000016.tif3566 (where R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 is as defined above), However, the compounds of formula (I), formula (II), formula (III), and formula (VI) may be substituted or unsubstituted dimethyl(3-bromophenylimino)diacetate, dimethyl 2,2'-(para-methylphenylimino)diacetate, bis(phenylmethyl) 2,2'-(2-bromoethylimino)diacetate, di-tert-butyl 2,2'-(2-bromoethylimino)diacetate, di-tert-butyl 2,2'-(benzylimino)diacetate, dibenzyl 2,2'-(2-bromoethylimino)diacetate, di-n-butyl 2,2'-(furan) N-(2-bromoethyl)-N-[2-(1,1-dimethylethyl)-N-methylphenylimino]diacetate, dimethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, dimethyl 2,2'-(bromoethylimino)diacetate, diisopropyl 2,2'-(para-methylphenylimino)diacetate, dimethyl 2,2'-(n-butylimino)diacetate, dimethyl 2,2'-(n-hexylimino)diacetate, ethyl 2-[(2-ethoxy-2-oxoethyl)-methylamino]-4-methylpentanoate, N-(2-bromoethyl)-N-[2-(1,1-dimethylethyl)-N-methylphenylimino]diacetate N-(2-tert-butoxy-2-oxoethyl)-L-isoleucine 1,1-dimethylethyl ether, N-(2-bromoethyl)-N-[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-phenylalanine 1,1-dimethylethyl ether, dimethyl 2,2'-(benzylimino)diacetate, diethyl 2,2'-(benzylimino)diacetate, N-(2-tert-butoxy-2-oxoethyl)-N-methylglycine ethyl ester, diethyl 2,2'-(2,5-dichlorophenylimino)diacetate, diethyl 2,2'-(5- bromo-2-methylphenylimino)diacetate, diethyl 2,2'-(5-iodo-2-methylphenylimino)diacetate, diethyl 2,2'-(5-bromo-4-fluoro-2-methylphenylimino)diacetate, methyl 2-((2-(tert-butoxy)-2-oxoethyl)(3-chlorophenyl)amino)propanoate, diethyl 2,2'-(n-hexylimino)diacetate, diethyl 2,2'-(n-octylimino)diacetate, di-tert-butyl 2,2'-(n-hexylimino)diacetate, dimethyl 2,2'-(Chloroethylimino)diacetate, 1-methyl-azepane-2,7-dicarboxylic acid dimethyl ester, 1-benzyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, 1-methyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, N-Boc-α-allylproline methyl ester, N-Boc-methanoproline ethyl ester, N-benzyl-2,6-dicarbomethoxypiperidine, 1-para- Not dichlorophenyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, di-tert-butyl 2,2'-dimethyl-2,2'-(methylimino)diacetate, dibenzyl-2,2'-diethyl-2,2'-(methylimino)diacetate, dibenzyl-2,2'-dibutyl-2,2'-(methylimino)diacetate, or di-tert-butyl 2,2'-diphenyl-2,2'-(methylimino)diacetate.

[0227] <Example> Determination of titanium content in Ziegler-Natta catalyst samples was performed using an Agilent 5110 inductively coupled plasma atomic emission spectrometer. The internal donor content in the catalyst was determined using an internal standard (1,2,4,5-tetramethylbenzene) in a mixture of CD2Cl2-CD3OD. 1 H NMR was performed on a Bruker AVANCE (400 MHz) or Agilent Technologies 400-MR (400 MHz) NMR spectrometer. 1 H and 13C NMR spectra were recorded. The content of xylene solubles in polymer samples was determined according to D 5492-17. The polydispersity index was determined as follows: The molecular weight distribution (MWD) of homopolypropylene and propylene-ethylene random copolymer samples was determined by gel permeation chromatography (GPC) on an Agilent PL-GPC 220 system according to ISO 16014-4:2012 "Plastics - Determination of average molecular weight and molecular weight distribution of polymers by size exclusion chromatography - Part 4: Method at elevated temperatures." The elution temperature was 150°C, and the solvent was 1,2,4-trichlorobenzene. <Examples 1 to 14> Synthesis of internal donors

[0228] Example 1. Synthesis of diethyl 2,2'-((2,6-diisopropylphenyl)imino)diacetate (D55) A mixture of 2,6-diisopropylaniline (8.00 g, 45.2 mmol), 2-bromoethyl acetate (25.0 mL, 37.7 g, 226 mmol), KI (0.60 g, 3.61 mmol), diisopropylethylamine (20.0 mL, 14.5 g, 112 mmol), and acetonitrile (100 mL) was refluxed for 48 h. The mixture was then poured into water (300 mL) and extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous NaSO, and the solvent was evaporated under reduced pressure (or in vacuo). Excess 2-bromoethyl acetate was removed by distillation under reduced pressure at 40 °C / 1 mbar. The residue was distilled in a Kugelrohr apparatus at 190° C. / 0.12 mbar to give 12.0 g (76%) of the product as an orange liquid which crystallized on standing. 1 H NMR(400MHz,CDCl3): δ 7.23-7.16(m,1H),7.14-7.08(m,2H),4.17(q,J-7.2Hz,4H),3.97(s,4H),3.65(sept,J-6.9Hz,2H),1.27(t,J=7.2Hz,6H),1.21(d,J=6.9Hz,12H).13 C NMR (101MHz, CDCl3): δ 171.7,148.4,145.9,126.9,124.4,60.5,56.5,27.8,24.7,14.2.

[0229] Example 2. Synthesis of diethyl 2,2'-((2,6-dimethylphenyl)imino)diacetate (D61) A mixture of 2,6-dimethylaniline (5.00 g, 41.3 mmol), ethyl 2-bromoacetate (36.4 mL, 55.2 g, 330 mmol), KI (0.55 g, 3.30 mmol), diisopropylethylamine (17.9 mL, 13.3 g, 112 mmol), and acetonitrile (120 mL) was refluxed for 48 h. After the reaction was complete, the mixture was poured into water (350 mL) and then extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous NaSO, and the solvent was evaporated under reduced pressure. Excess ethyl 2-bromoacetate was removed by distillation at 100 °C / 20 mbar under reduced pressure. The residue was purified by column chromatography (eluent: hexane / ethyl acetate=20 / 1, v / v) to give 12.6 g (96%) of the product as a dark orange liquid. 1 H NMR (400MHz, CDCl3): δ 7.08-7.01(m,2H),7.01-6.95(m,1H),4.16(q,J=7.2Hz,4H),3.98(s,4H),2.46(s,6H),1.27(t,J=7.2Hz,6H). 13 C NMR (101MHz, CDCl3): δ 171.9,147.6,136.5,128.9,125.2,60.4,54.6,18.9,14.1.

[0230] Example 3. Synthesis of dibutyl 2,2'-((2,6-diisopropylphenyl)imino)diacetate (D65) A mixture of 2,6-diisopropylaniline (3.90 g, 22.1 mmol), 2-bromobutyl acetate (12.9 g, 66.1 mmol), KI (0.20 g, 1.20 mmol), diisopropylethylamine (11.5 mL, 8.53 g, 66.1 mmol), and acetonitrile (100 mL) was refluxed for 72 hours. After the reaction was complete, the mixture was poured into water (350 mL) and then extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. Excess 2-bromobutyl acetate was removed by distillation under reduced pressure at 100 °C / 100 mbar. The residue was distilled in a Kugelrohr apparatus at 195° C. / 0.12 mbar to give 2.20 g (25%) of the product as a dark orange liquid. 1 H NMR(400MHz,CDCl3): δ 7.23-7.16(m,1H),7.14-7.08(m,2H),4.12(t,J=6.8Hz,4H),3.98(s,4H),3.65(sept,J=6.9 Hz,2H),1.69-1.53(m,4H),1.44-1.32(m,4H),1.21(d,J=6.9Hz,12H),0.94(t,J=7.4Hz,6H). 13 C NMR (101MHz, CDCl3): δ 171.8,148.5,145.9,126.9,124.4,64.4,56.3,30.6,27.8,24.7,19.1,13.7.

[0231] Example 4. Synthesis of diethyl 2,2'-((2-isopropylphenyl)imino)diacetate (D69) A mixture of 2-isopropylaniline (10.5 mL, 10.0 g, 74.0 mmol), 2-bromoethyl acetate (40.9 mL, 61.8 g, 370 mmol), KI (0.98 g, 5.92 mmol), diisopropylethylamine (32.3 mL, 23.9 g, 184 mmol), and acetonitrile (100 mL) was refluxed for 24 h. The mixture was then poured into water (350 mL) and extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous NaSO, and the solvent was evaporated under reduced pressure. Excess 2-bromoethyl acetate was removed by distillation at 100 °C / 20 mbar. The residue was distilled in a Kugelrohr apparatus at 170° C. / 0.20 mbar to give 20.4 g (88%) of the product as a dark orange liquid. 1 H NMR(400MHz,CDCl3): δ 7.36-7.30(m,1H),7.30-7.24(m,1H),7.15-7.09(m,2H),4.14(q,J-7.2Hz,4H),4.03(s,4H),3.58(sept,J- 6.9Hz, 1H), 1.24 (d, J = 6.9Hz, 6H), 1.23 (t, J = 7.2Hz, 6H). 13 C NMR (101MHz, CDCl3): δ 171.1,147.5,145.3,126.6,125.9,125.2,124.6,60.4,55.5,26.7,24.0,14.1.

[0232] Example 5. Synthesis of diethyl 2,2'-((2,6-diethylphenyl)imino)diacetate (D70) A mixture of 2,6-diethylaniline (10.0 g, 67.0 mmol), ethyl 2-bromoacetate (56.0 mL, 37.7 g, 335 mmol), KI (0.89 g, 5.36 mmol), diisopropylethylamine (29.3 mL, 21.7 g, 129 mmol), and acetonitrile (100 mL) was refluxed for 48 h. The mixture was then poured into water (350 mL) and extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous NaSO, and the solvent was evaporated under reduced pressure. Excess ethyl 2-bromoacetate was removed by distillation under reduced pressure at 40 °C / 1 mbar. The residue was distilled in a Kugelrohr apparatus at 160° C. / 0.24 mbar to give 20.1 g (93%) of the product as an orange liquid. 1 H NMR (400MHz, CDCl3): δ 7.18-7.08(m,3H),4.17(q,J=7.2Hz,4H),3.98(s,4H),2.87(q,J=7.5Hz,4H),1.26(t,J=7.5Hz,6H),1.27(t,J=7.2Hz,6H). 13 C NMR (101MHz, CDCl3): δ 171.7,147.1,143.1,126.6,126.1,60.4,55.8,23.9,15.2,14.1.

[0233] Example 6. Synthesis of diethyl 2,2'-(isopropylimino)diacetate (D71) A mixture of isopropylamine (7.25 mL, 5.00 g, 84.6 mmol), 2-bromoethyl acetate (23.4 mL, 35.3 g, 212 mmol), KI (1.12 g, 6.77 mmol), diisopropylethylamine (44.3 mL, 32.8 g, 254 mmol), and acetonitrile (150 mL) was refluxed for 24 h. After the reaction was complete, the mixture was poured into water (350 mL) and then extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. Excess 2-bromoethyl acetate was removed by distillation at 100 °C / 20 mbar. The residue was distilled under reduced pressure to give 17.7 g (90%) of the product as a clear greenish liquid (bp 90-92° C. / lmbar). 1 H NMR (400MHz, CDCl3): δ 4.08(q,J=7.1Hz,4H),3.43(s,4H),3.01(sept,J=6.5Hz,1H),1.18(t,J=7.1Hz,6H),0.98(d,J=6.5Hz,6H). 13 C NMR (101MHz, CDCl3): δ 171.9,60.2,52.5,52.3,19.7,14.0.

[0234] Example 7. Synthesis of diethyl 2,2'-((2,6-dibromophenyl)imino)diacetate (D72) A mixture of 2,6-dibromo-4-methylaniline (10.0 g, 37.7 mmol), ethyl 2-bromoacetate (20.9 mL, 31.5 g, 189 mmol), KI (0.50 g, 3.02 mmol), diisopropylethylamine (16.5 mL, 12.2 g, 94.4 mmol), and acetonitrile (100 mL) was stirred in a glass pressure vessel at 125 °C for 10 days. The reaction was monitored using GC-MS. After completion of the reaction, the mixture was poured into water (350 mL) and then extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. Excess ethyl 2-bromoacetate was removed by distillation under reduced pressure at 40 °C / 1 mbar. The residue was purified by column chromatography (eluent: hexane / ethyl acetate=10 / l, v / v) to give 6.64 g (40%) of the product as a yellow oily liquid. 1 H NMR (400MHz, CDCl3): δ 7.37-7.32(m,2H),4.15(q,J=7.2Hz,4H),4.02(s4H),2.25(s,3H),1.24(t,J=7.2Hz,6H). 13 C NMR(101HMz,CDCl3): δ 170.5,143.5,138.2,133.6,125.0,60.6,54.7,20.1,14.1.

[0235] Example 8. Synthesis of diethyl 2,2'-((2-methylcyclohexyl)imino)diacetate (D77) A mixture of 2-methylcyclohexane-l-amine (a mixture of cis and trans isomers, 11.7 mL, 10.0 g, 88.5 mmol), ethyl 2-bromoacetate (20.7 mL, 31.0 g, 186 mmol), KI (7.34 g, 44.2 mmol), diisopropylethylamine (46.1 mL, 34.2 g, 265 mmol), and acetonitrile (100 mL) was refluxed for 24 h. The mixture was then poured into water (350 mL) and extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous NaSO, and the solvent was evaporated under reduced pressure. Excess ethyl 2-bromoacetate was removed by distillation at 100 °C / 20 mbar. The residue was distilled in a Kugelrohr apparatus at 120°C / 0.12 mbar to give 21.2 g (84%) of the product (mixture of isomers) as a pale yellow liquid. 1 H NMR (400 MHz, CDCl3): δ 4.17-4.05 (m, 4H), 3.61-3.40 (m, 4H), 2.95-1.81 (m, 2H), 1.85-1.26 (m, 5H), 1.26-0.83 (m, 12H). For a mixture of isomers 13 C NMR (101MHz, CDCl3): δ 172.4, 172.2, 68.1, 62.0, 60.2, 60.1, 52.5, 52.2, 36.1, 35.3, 31.7, 30.7, 27.8, 26.2, 26.0, 25.8, 24.6,19.4,19.3,14.14,14.11,11.5.

[0236] Example 9. Synthesis of ethyl l-(2-ethoxy-2-oxoethyl)indoline-2-carboxylate (D79) 1. Ethyl indoline-2-carboxylate TIFF2025539733000025.tif20107 To a solution of indoline-2-carboxylic acid (10.0 g, 62.0 mmol) in absolute ethanol (100 ml) was added thionyl chloride (4.90 ml, 8.04 g, 67.0 mmol) dropwise at room temperature, and the reaction mixture was stirred at 50 °C for 12 hours. It was then poured in portions into a saturated aqueous solution of NaHCO (300 ml) and extracted with dichloromethane (3 × 150 ml). The combined organic extracts were washed with water (100 ml) and dried over anhydrous NaSO. The solvent was evaporated under reduced pressure, and the residue was dried under reduced pressure to give 10.2 g (86%) of the product as a pale yellow oil. 1 H NMR(400MHz,CDCl3): δ 7.10(d,J=7.3Hz,1H),7.06(t,J=7.5Hz,1H),6.76(t,J=7.5Hz,1H),6.74(d,J=7.8Hz,1H),4.38(dd,J=10 .2,5.6Hz,1H),4.21(dq,J=7.2,0.9Hz,2H),4.00-4.14(m,1H),3.30-3.44(m,2H),1.30(t,J=7.2Hz,3H). 13 C NMR (101MHz, CDCl3): δ 173.4,149.8,127.2,126.3,124.0,119.0,109.7,61.0,59.5.

[0237] 2. Ethyl l-(2-ethoxy-2-oxoethyl)indoline-2-carboxylate (D79) A mixture of ethyl indoline-2-carboxylate (5.00 g, 26.1 mmol), ethyl 2-bromoacetate (2.91 mL, 4.37 g, 26.4 mmol), KI (0.86 g, 5.20 mmol), diisopropylethylamine (6.80 mL, 5.05 g, 39.3 mmol), and acetonitrile (50 mL) was refluxed for 12 h. The mixture was then poured into water (350 mL) and extracted with dichloromethane (3 × 100 mL). The combined organic extracts were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: hexane / ethyl acetate = 10 / L, v / v) to give 5.20 g (72%) of the product as a colorless oil. 1 H NMR(400MHz,CDCl3):δ 7.05(t,J=6.9Hz,1H),7.03(d,J=7.2Hz,1H),6.69(t,J=7.3Hz,1H),6.38(d,J=8.2Hz,1H),4.56 (dd,J=10.5,8.9Hz,1H),3.98-4.29(m,6H),3.40-3.47(m,1H),3.18-3.24(m,1H),1.29(t,J=7.2 Hz,3H),1.23(t,J=7.1Hz,1H). 13 C NMR (101MHz, CDCl3): δ 172.5,170.1,150.3,127.6,127.0,124.2,118.7,106.6,64.9,61.2,60.8,48.5,33.2,14.18,14.16.

[0238] Example 10. Synthesis of diethyl 2,2'-((2,6-difluorophenyl)imino)diacetate (D80) To a mixture of 2,6-difluoroaniline (10.0 g, 77.5 mmol), pyridine (18.7 mL, 18.4 g, 233 mmol), and KI (6.43 g, 38.7 mmol) in a glass pressure vessel, ethyl 2-bromoacetate (40 mL, 60.4 g, 362 mmol) was added dropwise over 10 min. The vessel was then closed, and the reaction mixture was stirred at 125 °C for 7 days until the 2,6-difluoroaniline was consumed. After cooling (or upon cooling), the solidified mixture was crushed, and water (50 mL) and dichloromethane (50 mL) were added. The organic phase was separated, and the aqueous phase was extracted with dichloromethane (3 × 25 mL). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated. Excess ethyl 2-bromoacetate was distilled off at 100°C / 20 mbar. The monoalkylation by-product (ethyl (2,6-difluorophenyl)glycinate) was distilled off in a Kugelrohr apparatus at 80°C / 0.08 mbar. The residue was distilled in a Kugelrohr apparatus at 120°C / 0.08 mbar to give 8.30 g (36%) of the product as a pale yellow liquid. 1 H NMR (400MHz, CDCl3): δ 6.94-6.77(m,3H),4.18(q,J=7.2Hz,4H),4.10(s,4H),1.26(t,J=7.1Hz,6H). 13 C NMR(101MHz,CDCl3): δ 171.0(s,2C),157.3(dd,J=6.8,246.7Hz,2C),126.4-126.1(m,1C),122.7-12 2.5(m,1C),112.2-112.0(m,2C),60.8(s,2C),54.3-54.2(m,2C),14.1(s,2C). 19 F NMR (376MHz, CDCl3): δ -120.1-(-120.2)(m, 2F).

[0239] Example 11. Synthesis of diethyl 2,2'-(isobutylimino)diacetate (D81) A mixture of isobutylamine (5.00 mL, 3.68 g, 50.4 mmol), 2-bromoethyl acetate (11.8 mL, 17.7 g, 106 mmol), KI (4.18 g, 25.2 mmol), diisopropylethylamine (26.0 mL, 19.5 g, 151 mmol), and acetonitrile (50 mL) was refluxed for 24 hours. The mixture was then poured into water (300 mL) and extracted with dichloromethane (3 × 50 mL). The combined organic extracts were dried over anhydrous NaSO, and the solvent was evaporated under reduced pressure. Excess 2-bromoethyl acetate was removed by distillation under reduced pressure at 100 °C / 20 mbar. The residue was distilled in a Kugelrohr apparatus at 80° C. / 0.20 mbar to give 7.62 g (88%) of the product as a pale yellow liquid. 1 H NMR (400MHz, CDCl3): δ 4.11(q,J=7.1Hz,4H),3.49(s,4H),2.43(d,J=7.3Hz,2H),1.75-1.56(m,1H),1.22(t,J=7.2Hz,6H),0.86(d,J=6.6Hz,6H). 13 C NMR (101MHZ, CDCl3): δ171.4,62.4,60.2,55.3,26.7,20.4,14.1.

[0240] Example 12. Synthesis of bis(4-chloro-3,5-dimethylphenyl) 2,2'-((2,6-diethylphenyl)imino) diacetate (D83) TIFF2025539733000029.tif251171. 2,2'-((2,6-diethylphenyl)imino)diacetic acid A mixture of diethyl 2,2'-((2,6-diethylphenyl)imino)diacetate (12.8 g, 39.8 mmol), KOH (9.20 g, 164 mmol), EtOH (120 mL), and water (25 mL) was refluxed for 12 h. The mixture was then rotary evaporated to dryness, the residue was dissolved in water (200 mL), and the solution was then acidified to pH 1 with concentrated HCl. The resulting mixture was stirred for 12 h, and the precipitate was filtered and dissolved in diethyl ether (100 mL). The ether solution was dried over anhydrous Na2SO4, the solvent was evaporated under reduced pressure, and the residue was dried under reduced pressure. The yield was 8.83 g (87%) of product as a pale yellow solid. 1 HNMR (400MHz, CDCl3): δ 11.86(br. s,2H),7.22-7.15(m,1H),7.15-7.08(m,2H),3.97(s,4H),2.73(q,J=7.5Hz,4H),1.24(t,J=7.5Hz,6H). 13 C NMR(101MHZ, CDCl3): δ 176.8,147.5,142.5,127.6,127.4,60.6,24.5,15.4.

[0241] 2. Bis(4-chloro-3,5-dimethylphenyl) 2,2'-((2,6-diethylphenyl)imino) diacetate (D83) To a solution of 2,2'-((2,6-diethylphenyl)imino)diacetic acid (3.00 g, 11.3 mmol), 4-chloro-3,5-dimethylphenol (4.43 g, 28.3 mmol), and 4-dimethylaminopyridine (DMAP, 0.55 g, 4.52 mmol) in dichloromethane (300 ml) was added N,N'-dicyclohexylcarbodiimide (DCC, 5.83 g, 28.3 mmol) at 0 °C. The mixture was then stirred at the same temperature for 1 h and then at room temperature for 15 h. The reaction mixture was filtered, and the filtrate was washed with water (3 × 200 ml), dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The remaining DCC was removed by distillation in a Kugelrohr apparatus at 120 °C / 20 mbar. The residue was purified by column chromatography (eluent: hexane / ethyl acetate = 7 / 1, v / v), and the resulting material was washed with hexane (40 ml) to give 6.14 g (75%) of the product as a white crystalline solid. 1 H NMR (400MHz, CDCl3): δ 7.26-7.15(m,3H),6.84(s,4H),4.29(s,4H),2.95(q,J=7.5Hz,4H),2.38(s,12H),1.31(t,J=7.5Hz,6H). 13 C NMR (101MHz, CDCl3): δ 170.2,148.0,146.9,143.2,137.5,131.8,126.9,126.7,121.2,56.3,24.1,20.8,15.3.

[0242] Example 13. Synthesis of diethyl 2,2'-(cyclohexylimino)diacetate (D84) A mixture of cyclohexylamine (3.00 mL, 2.60 g, 26.2 mmol), 2-bromoethyl acetate (6.00 mL, 8.93 g, 167 mmol), KI (2.20 g, 13.8 mmol), diisopropylethylamine (14.0 mL, 10.1 g, 78.3 mmol), and acetonitrile (30 mL) was refluxed for 24 h. After the reaction was complete, the resulting mixture was poured into water (200 mL) and then extracted with dichloromethane (3 × 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. Excess 2-bromoethyl acetate was removed by distillation at 100 °C / 20 mbar reduced pressure. The residue was purified by column chromatography (eluent: hexane / ethyl acetate=7 / 3, v / v) to give 3.24 g (46%) of the product as a pale orange liquid. 1 H NMR (400MHz,CDCl3): δ 4.12(q,J=7.1Hz,4H),3.53(s,4H),2.70-2.54(m,1H),1.90-1.77(m,2H),1. 77-1.65(m,2H),1.61-1.49(m,1H),1.23(t,J=7.1Hz,6H),1.19-0.94(m,5H). 13 C NMR (101MHz, CDCl3): δ 172.2,61.1,60.3,52.7,30.5,25.8,25.5,14.1.

[0243] Example 14. Synthesis of diethyl l-isopropylpyrrolidine-2,5-dicarboxylate (D85) A mixture of diisopropylethylamine (8.83 mL, 50.7 mmol), potassium iodide (1.41 g, 8.45 mmol), isopropylamine (1.38 mL, 16.9 mmol), diethyl 2,5-dibromoadipate (6.09 g, 16.9 mmol), and 10 mL of acetonitrile was stirred at 80 °C for 3 days. It was then poured into 100 mL of saturated aqueous NaHCO3. The resulting mixture was extracted with 3 × 70 mL of dichloromethane, and the combined organic extracts were washed with 100 mL of water, dried over Na2SO4, and the solvent was evaporated under reduced pressure. The product was isolated by vacuum distillation in a Kugelrohr apparatus (0.1 mbar, 110° C.) Yield: 2.2 g (51%, mixture of cis and trans isomers in a 1 / 1 molar ratio) of product as a yellow oil. 1 H NMR(CDCl3,400MHz): δ 4.08-4.21(m,4H,cis+trans),3.87-3.91(m,2H,trans+cis),3.54-3.58(m,2H,trans+cis ),3.09(sept,J=6.6Hz,1H,cis),2.99(sept,J=6.4Hz,1H,trans),2.26-2.37(m,2H,trans or cis),1.92-2.08(m,4H,trans or cis),1.76-1.84(m,2H,trans or cis,1.23(t,J=7.2Hz,6H,trans or cis),1.22(t,J=7.2Hz,6H,trans or cis,1.05(d,J=6.4Hz,3H,trans,0.99(d,J=6.6Hz,6H,cis,0.99(d,J=6.4Hz,3H,trans). 13 C NMR(CDCl3,400MHz): δ 175.5,174.8,63.2,62.1,60.31,60.26,51.2,50.4,29.8,29.1,22.7,22.0,19.0,14.13 * (Trans), 14.07 * (transformer).

[0244] Example 15. Synthesis of diethyl 2,2'-((4-bromo-2,6-diethylphenyl)imino)diacetate (D93) To a solution of diethyl 2,2'-((2,6-diethylphenyl)imino)diacetate (D70) (5.00 g, 15.6 mmol) in dichloromethane (50 ml), N-bromosuccinimide (2.77 g, 15.6 mol) was added portionwise at room temperature for 30 minutes. The reaction mixture was then stirred at the same temperature for 12 hours. The mixture was poured into water (200 ml), the organic phase was separated, and the aqueous phase was extracted with dichloromethane (3 × 50 ml). The combined organic extracts were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: hexane / ethyl acetate = 5 / L, v / v) to give 2.95 g (47%) of the product as a dark red oil. 1 H NMR (400MHz, CDCl3): δ 7.20(s,2H),4.15(q,J=7.2Hz,4H),3.92(s,4H),2.82(q,J=7.5Hz,4H),1.25(t,J=7.2Hz,3H),1.23(t,J=7.5Hz,3H). 13 C NMR (101MHz, CDCl3): δ 171.5,146.1,145.4,129.5,119.8,60.6,55.5,23.9,15.0,14.2.

[0245] Example 16. Synthesis of diethyl 2,2'-((2,6-dichlorophenyl)imino)diacetate (D94) TIFF2025539733000034.tif31117 To a mixture of 2,6-dichloroaniline (7.00 g, 43.2 mmol), pyridine (10.5 mL, 10.2 g, 129 mmol), and KI (3.60 g, 21.6 mmol) in a glass pressure vessel, ethyl 2-bromoacetate (48.0 mL, 72.1 g, 432 mmol) was added dropwise over 10 min. The vessel was then closed, and the reaction mixture was stirred at 125 °C for 5 days until the 2,6-dichloroaniline was consumed. After cooling, the solidified mixture was crushed, and water (50 mL) and dichloromethane (50 mL) were added. The organic phase was separated, and the aqueous phase was extracted with dichloromethane (3 × 25 mL). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated. Excess 2-bromoethyl acetate was distilled off at 100°C / 20 mbar. The monoalkylation by-product (ethyl (2,6-dichlorophenyl)glycinate) was distilled off in a Kugelrohr apparatus at 90°C / 0.08 mbar. The residue was distilled in a Kugelrohr apparatus at 125°C / 0.08 mbar to give 7.72 g of a mixture, which was purified by column chromatography (eluent: dichloromethane) to give 4.81 g (33%) of the product as a dark red oil. 1 H NMR (400MHz, CDCl3): δ 7.30(d,J=8.0Hz,2H),7.04-6.98(m,1H),4.16(q,J=7.2Hz,4H),4.08(s,4H),1.25(t,J=7.2Hz,6H). 13 C NMR (101MHz, CDCl3): δ 170.8,143.5,134.9,129.3,126.4,60.7,54.4,14.1.

[0246] Example 17. Synthesis of diethyl 2,2'-((2,6-dibromo-4-methoxyphenyl)imino)diacetate (D105) TIFF2025539733000035.tif35119To a mixture of 2,6-dibromo-4-methoxyaniline (7.00 g, 25.0 mmol), pyridine (6.10 mL, 5.93 g, 75.0 mmol), and KI (2.09 g, 12.5 mmol) in a glass pressure vessel, 2-bromoethyl acetate (27.8 mL, 41.8 g, 250 mmol) was added dropwise over 10 min. The vessel was then closed, and the reaction mixture was stirred at 125 °C for 7 days until the 2,6-dibromo-4-methoxyaniline was consumed. After cooling, the solidified mixture was crushed, and water (50 mL) and dichloromethane (50 mL) were added. The organic phase was separated, and the aqueous phase was extracted with dichloromethane (3 × 25 mL). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated. Excess 2-bromoethyl acetate was distilled off at 100 °C / 20 mbar. The monoalkylation by-product (ethyl (2,6-dibromo-4-methoxyphenyl)glycinate) was distilled off in a Kugelrohr apparatus at 150 °C / 0.5 mbar. The residue was purified by column chromatography (eluent: dichloromethane) to give 1.85 g (16%) of the product as a dark red oil. 1 H NMR (400MHz, CDCl3): δ 7.10(s,2H),4.17(q,J=7.2Hz,4H),4.01(s,4H),3.76(s,3H),1.26(t,J=7.2Hz,6H). 13 C NMR (101MHz, CDCl3): δ 170.3,157.4,139.2,125.8,118.3,60.3,55.6,54.7,14.0.

[0247] Examples 18-34, Comparative Example C35. General Procedure for the Preparation of Ziegler-Natta Catalysts A mixture of MgCl (1.10 g), phthalic anhydride (0.27 g), epichlorohydrin (1.81 ml), tributyl phosphate (2.29 ml), and toluene (16 ml) was placed in a round-bottom flask and stirred at 60 °C for 2 hours on a magnetic stirrer at 400 rpm. The mixture was then cooled to -30 °C, and TiCl (12.5 ml) was slowly added dropwise so that the temperature of the reaction mixture did not exceed -25 °C. After complete addition of TiCl, the resulting mixture was warmed to room temperature and then stirred at 85 °C for 2 hours. The first portion of the internal donor (1.31 mmol) in toluene (5 ml) was then added, and stirring was continued at this temperature for 1 hour. The resulting mixture was filtered hot, and the solid precipitate was suspended in toluene (15 ml). A second portion of the internal donor (0.69 mmol) in toluene (5 ml) was added to the resulting suspension, and the resulting mixture was stirred at 85°C for 1 hour, filtered, and the filter cake was washed with toluene (3 × 10 ml). The solid precipitate was suspended in a 10% (wt.) toluene solution of TiCl4 (22 ml). The resulting suspension was then maintained under stirring at 95°C for 1 hour and filtered again while hot. The latter operation was repeated three times, with the difference that the suspension was maintained at 110°C for 30 minutes under stirring. The solid precipitate was then washed with hexane (4 × 20 ml) and dried in vacuo. The powdered catalyst thus obtained was recovered and stored in an inert atmosphere. The analytical data are shown in Table 1.

[0248] Examples 36-52, Comparative Example C53. General Procedure for Propylene Polymerization Hexane was degassed by bubbling with argon and dried over 4A molecular sieves. Polymerization-grade propylene was used. Preparation of the catalyst slurry and its introduction into the reactor were carried out in a box with a controlled nitrogen atmosphere (<1 ppm water, <1 ppm O). Polymerization was carried out in a 100 ml reactor equipped with a mechanical stirrer, a pressure gauge, a 200 bar rupture valve, a gas inlet, a PTFE insert, and a unit for loading the catalyst suspension, consisting of a 40 ml pressure vessel, which was filled with gas (propylene) under pressure exceeding the pressure in the reactor during polymerization and connected to a 6.5 ml container for the catalyst suspension, connected to the reactor and separated from the reactor and pressure vessel by ball valves. The catalyst suspension was fed into the reactor by applying propylene overpressure by continuously opening both ball valves for 2 seconds.

[0249] Catalyst powder (4.9–5.5 mg) and 1 ml of hexane were placed in a 4 ml glass vial equipped with a magnetic stirrer and a screw cap with a PTFE gasket. The catalyst powder was then suspended in hexane while stirring on the magnetic stirrer for 30 minutes. 60 equivalents (per titanium) of triethylaluminum, 12 equivalents (per titanium) of external donor (ED, Ph2Si(OMe)2), and 2.5 ml of hexane were then added to the resulting suspension. Hexane (32 ml) and another 60 equivalents (per titanium) of triethylaluminum were then added to the reactor, which was then closed. The catalyst powder slurry was then transferred to a catalyst suspension vessel connected to the reactor, and the remaining volume of the vessel (approximately 2 ml) was filled with hexane. The nitrogen atmosphere in the reactor was replaced with propylene by repeatedly pressurizing the reactor with 10 bar of propylene and then venting the excess pressure. The reactor was then heated to 60°C with stirring. At this temperature, hexane was saturated with propylene by supplying propylene gas through the gas inlet at a pressure of 5 bar. The catalyst was then supplied to the reactor with an overpressure of propylene (10 bar). Polymerization was then carried out at a temperature of 70±1°C for 20 to 40 minutes. The polymerization was terminated, and the excess propylene pressure was released. The reactor was then opened, and volatile materials were removed in vacuo. The polymer thus obtained was dried in vacuo to a constant weight and weighed. The activity was calculated as the weight (kg) of polymer produced per hour per gram of catalyst. The polymerization data are shown in Table 1. Table 1 TIFF2025539733000036.tif207169

[0250] The present disclosure is not limited to the embodiments and examples contained herein, but is specifically intended to include modifications of those embodiments, including portions of the embodiments and combinations of elements of different embodiments, as falling within the scope of the following claims. The following is the invention as originally described in the present application.

[0251] The following is the invention as originally described in the present application. <Claim 1> 1. A procatalyst for olefin polymerization comprising a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor which is a compound of formula (I): The internal electron donor has the formula (I) TIFF2025539733000037.tif4064, R 1 is one or more identical or different substituents R 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 2 , R 3 , R 4 and R 5 is hydrogen, one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 6 and R 7 is one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 1 ~R 9 may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. <Claim 2> R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 9 Each of the C1~C 20 Straight or branched chain alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 is C1~C 20 Straight or branched chain alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl; C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Straight or branched alkyl, preferably C1-C 10 2. The procatalyst of claim 1, wherein the alkyl group is selected from the group consisting of: straight chain or branched alkyl, more preferably C1 to C6 straight chain or branched alkyl. <Claim 3> R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 9is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; and R is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. <Claim 4> R 2 , R 3 , R 4 and R 5 10. The procatalyst of claim 1, wherein each of is independently hydrogen. <Claim 5> The internal electron donor is represented by formula (II) TIFF2025539733000038.tif3066, wherein R 10 ,R 11 and R 12 is one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, each R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 10 ~R 12 Optionally, any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. <Claim 6> R 9 , R 10 , R 11 , and R 12 Each of the C1~C 20 Straight or branched chain alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 teeth, C1~C 20 Straight or branched chain alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl; C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Straight or branched chain alkyl, preferably C1-C 10 It is a straight or branched chain alkyl, more preferably a C1 to C6 straight or branched chain alkyl. 6. The procatalyst of claim 5, independently selected from the group consisting of: <Claim 7> R 9 , R 10 , R 11 , and R 12each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl). <Claim 8> The internal electron donor is represented by formula (III) TIFF2025539733000039.tif5269 compound, R in the formula 13 and R 14 is one or more of the same or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: R 15 and R 16 teeth, Hydrogen, alkyl or cycloalkyl, optionally substituted aryl, halogen, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 13 and R 14 may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings; R28 is selected from the group consisting of hydrogen and -O-alkyl. <Claim 9> R 9 , R 13 , R 14 , R 15 , and R 16 Each of the C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 teeth, C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 linear or branched alkyl); R 28 is hydrogen and -O-alkyl (where alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 It is a straight chain or branched alkyl, more preferably a C1 to C6 straight chain or branched alkyl. 9. The procatalyst of claim 8, wherein <Claim 10> R 9 , R 13 , R 14 , R 15 , and R 16 each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; R 28 10. The procatalyst of claim 9, wherein is selected from the group consisting of hydrogen and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. <Claim 11> R 15 and R 16 9. The procatalyst of claim 8, wherein each of is independently a halogen, preferably selected from the group consisting of F, Cl, Br, and I. <Claim 12> The internal electron donor is represented by formula (IV) TIFF2025539733000040.tif3862, R 18 and R 19 is one or more of the same or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 20 , R 21 , R 22 and R 23is hydrogen, one or more of the same or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 18 ~R 23 Optionally, any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. <Claim 13> R 9 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 Each of the C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 but, C1~C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Straight or branched alkyl, preferably C1-C 10 13. The procatalyst of claim 12, wherein the alkyl group is selected from the group consisting of: a straight chain or branched chain alkyl; <Claim 14> R 9 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl). <Claim 15> R 20 , R 21 , R 22 and R 23 13. The procatalyst of claim 12, wherein each of is hydrogen. <Claim 16> The internal electron donor is Diethyl 2,2'-(isopropylimino)diacetate, Diethyl 2,2'-(2,6-diethylphenylimino)diacetate, Diethyl 2,2'-(2,6-diisopropylphenylimino)diacetate, Diethyl 2,2'-(2-isopropylphenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(2,6-difluorophenylimino)diacetate, Diethyl 2,2'-(2,6-dibromo-4-methylphenylimino)diacetate, Diethyl 2,2'-(2,6-dichlorophenylimino)diacetate, Diethyl 2,2'-(4-bromo-2,6-diethylphenylimino)diacetate, Diethyl 2,2'-(2,6-dibromo-4-methoxyphenylimino)diacetate, Diethyl 2,2'-(2-methylcyclohexylimino)diacetate, di-n-butyl (2,6-di-tert-butylphenylimino) diacetate, Diethyl 2,2'-(2-para-methylphenyl-4,6-dimethylphenylimino)diacetate, diethyl 2,2'-(N-indan-1-ylimino)diacetate, Diethyl 2-(3,5-dimethylphenyl)-2,2'-(isopropylimino)diacetate, ethyl 2-(2-(ethoxycarbonyl)indolin-1-yl)acetate, bis(3,5-dimethyl-4-chlorophenyl) 2,2'-(2,6-diethylphenylimino) diacetate, Diethyl (2S,5S)-(N-isopropyl)-pyrrolidine-2,5-diformate, N-isopropyl-N-(2-ethoxy-2-ketoethyl)-alpha-amino-gamma-butyrolactone, ethyl alpha-(N-isopropyl-N-(1-(ethoxycarbonyl)cyclohexyl)amino)acetate, 4-(2,6-diethylphenyl)-2,6-dioxo-4-aza-l,7-dioxecan, Diethyl 2,2'-(para-(triethylsilyl)phenylimino)diacetate, Diethyl 2,2'-(meta-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-(ortho-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-((dimethylphenylsilyl)ethylimino)diacetate, and Bis(trimethylsilylmethyl) 2,2'-(isopropylimino)diacetate 16. The procatalyst of claim 15, selected from the group consisting of: <Claim 17> (a) contacting a magnesium-containing compound with a titanium-containing compound; (b) adding an internal electron donor to the mixture obtained in step (a), wherein the internal electron donor is a compound represented by formula (I) TIFF2025539733000041.tif4263 compound, R in the formula 1 is one or more identical or different substituents R 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 2 , R 3 , R 4 and R 5 is hydrogen, one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 6 and R 7 is one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R1 ~R 9 and wherein any of the above may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings. <Claim 18> (a) a procatalyst for olefin polymerization according to any one of claims 1 to 16; (b) a cocatalyst, and (c) an external electron donor; 1. A catalyst system for olefin polymerization comprising: <Claim 19> 20. The catalyst system of claim 18, wherein the co-catalyst comprises an organoaluminum compound. <Claim 20> The organoaluminum compound is represented by the following formula: AlR 24 m X 3-m , is a compound of During the ceremony, R 24 is selected from hydrocarbon groups having 1 to 20 carbon atoms; 20. The catalyst system of claim 19, wherein X is a halogen atom and m is greater than 0 and less than or equal to 3. <Claim 21> 21. The catalyst system of claim 20, wherein the organoaluminum compound is selected from the group consisting of trialkylaluminums, trialkenylaluminums, dialkylaluminum halides, alkylaluminum sesquihalides, alkylaluminum dihalides, dialkylaluminum hydrides, and other partially hydrogenated alkylaluminums. <Claim 22> 22. The catalyst system of claim 21, wherein the organoaluminum compound is selected from the group consisting of triethylaluminum, triisobutylaluminum, tri-n-butylaluminum, tri-n-hexylaluminum, and tri-n-octylaluminum, triisoprenylaluminum, diethylaluminum chloride, dibutylaluminum chloride, and diethylaluminum bromide, ethylaluminum sesquichloride, butylaluminum sesquichloride, and ethylaluminum sesquibromide, ethylaluminum dichloride, n-propylaluminum dichloride, butylaluminum dibromide, diethylaluminum hydride, dibutylaluminum hydride, ethylaluminum dihydride, and n-propylaluminum dihydride. <Claim 23> 23. The catalyst system of any one of claims 19 to 22, wherein the organoaluminum compound is present in the catalyst system in an amount such that the molar ratio of aluminum to titanium present in the procatalyst is from about 0.1 to about 2000, preferably from about 5 to about 1000, more preferably from about 10 to about 700, and even more preferably from about 25 to about 400. <Claim 24> 24. The catalyst system according to any one of claims 18 to 23, wherein the external electron donor is selected from the group consisting of silicon compounds, ethers, esters, amines, and heterocyclic compounds. <Claim 25> The external donor has the formula: (R 25 ) a (R 26 ) b Si(OR 27 ) c , is a compound of During the ceremony a and b are integers of 0 to 2, c is an integer of 1 to 4, and the sum (a+b+c) is 4; R 25 , R 26 , and R 2725. The catalyst system according to claim 18, wherein is a radical having 1 to 18 carbon atoms, which may contain heteroatoms. <Claim 26> a is 1, b is 1, c is 2, and R 25 and R 26 at least one of R is selected from a branched alkyl, cycloalkyl, or aryl group having 3 to 10 carbon atoms, which may contain heteroatoms; 27 C1~C 10 26. The catalytic system of claim 25, wherein the alkyl group is preferably methyl. <Claim 27> 27. The catalyst system of claim 26, wherein the external electron donor is selected from the group consisting of methylcyclohexyldimethoxysilane, diphenyldimethoxysilane, methyl-t-butyldimethoxysilane, dicyclopentyldimethoxysilane, diisopropyldimethoxysilane, (2-ethylpiperidinyl)t-butyldimethoxysilane, (2-ethylpiperidinyl)thexyldimethoxysilane, (3,3,3-trifluoro-n-propyl)(2-ethylpiperidinyl)dimethoxysilane, methyl(3,3,3-trifluoro-n-propyl)dimethoxysilane, and N,N-diethylaminotriethoxysilane. <Claim 28> a is 0, c is 3, and R 26 is a branched alkyl or cycloalkyl group which may contain heteroatoms, and R 27 26. The catalyst system of claim 25, wherein is methyl. <Claim 29> 26. The catalyst system of claim 25, wherein the external electron donor is selected from the group consisting of cyclohexyltrimethoxysilane, t-butyltrimethoxysilane, and hexyltrimethoxysilane. <Claim 30> 30. The catalyst system according to any one of claims 18 to 29, wherein the external electron donor is used in an amount such that the molar ratio between the cocatalyst and the external electron donor is between 0.1 and 500, preferably between 1 and 300, more preferably between 3 and 100. <Claim 31> 17. A method for preparing a catalyst system for olefin polymerization, comprising contacting the procatalyst of any one of claims 1 to 16 with a cocatalyst and an external electron donor. <Claim 32> 31. A process for the (co)polymerization of olefins, comprising contacting at least one olefin monomer with a catalyst system according to any one of claims 18 to 30. <Claim 33> as an internal electron donor in a catalyst for olefin polymerization TIFF2025539733000042.tif4469, wherein R 1 is one or more identical or different substituents R 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 2 , R 3 , R 4 and R 5 is hydrogen, one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 6 and R 7 is one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 1 ~R 9 may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings. <Claim 34> R 1 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 9 Each of the C1~C 20 Straight or branched chain alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 Aryl are independently selected from the group consisting of R 8 teeth, C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl; C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 It is a straight chain or branched alkyl, more preferably a C1 to C6 straight chain or branched alkyl. 34. The use according to claim 33, selected from the group consisting of: <Claim 35> R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 9each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. <Claim 36> R 2 , R 3 , R 4 , and R 5 34. The use of claim 33, wherein each of is hydrogen. <Claim 37> The compound of formula (I) is represented by formula (II) TIFF2025539733000043.tif3171 compound, R in the formula 10 ,R 11 and R 12 is one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, each R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 10 ~R 12may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings. <Claim 38> R 9 , R 10 , R 11 and R 12 Each of the C1-C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3-C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6-C 20 Aryl, preferably C6-C 10 Aryl are independently selected from the group consisting of R 8 but, C1-C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3-C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6-C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 It is a straight chain or branched alkyl, more preferably a C1 to C6 straight chain or branched alkyl. 38. The use according to claim 37, selected from the group consisting of: <Claim 39> R 9 , R 10 , R 11 , and R 12are independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; and R8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. <Claim 40> The compound of formula (I) is represented by formula (III) TIFF2025539733000044.tif5068 compound, R in the formula 13 and R 14 is one or more of the same or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3, independently selected from the group consisting of R 15 and R 16 represents hydrogen, alkyl or cycloalkyl, optionally substituted aryl, halogen, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 13 and R 14 may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings; R 2834. The use of claim 33, wherein is selected from the group consisting of hydrogen, -O-alkyl. <Claim 41> R 9 , R 13 , R 14 , R 15 , and R 16 Each of the C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 teeth, C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 linear or branched alkyl); R 28 is hydrogen and -O-alkyl (where alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 The use according to claim 40, wherein the alkyl group is selected from the group consisting of straight chain or branched alkyl, more preferably C1 to C6 straight chain or branched alkyl. <Claim 42> R 9 , R 13 , R 14 , R 15 , and R 16 each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl); R 28 is selected from the group consisting of hydrogen and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. <Claim 43> R 15 and R 16 41. The use according to claim 40, wherein each of is independently a halogen, preferably selected from the group consisting of F, Cl, Br and I. <Claim 44> The compound of formula (I) is represented by formula (IV) TIFF2025539733000045.tif3964 compound, R in the formula 18 and R 19 is one or more of the same or different substituents R 8 R is independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with 20 , R 21 , R 22 , and R 23 is hydrogen, one or more of the same or different substituents R 8independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 18 ~R 23 may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings. <Claim 45> R 9 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 Each of the C1~C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 teeth, C1~C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10aryl, and -O-alkyl (wherein alkyl is C1-C 20 Straight or branched alkyl, preferably C1-C 10 45. The use according to claim 44, wherein the alkyl group is selected from the group consisting of: straight chain or branched alkyl, more preferably C1 to C6 straight chain or branched alkyl. <Claim 46> R 9 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 are independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; and R8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. <Claim 47> R 20 , R 21 , R 22 , and R 23 45. The use of claim 44, wherein each of is hydrogen. <Claim 48> The compound of formula (I) is diethyl 2,2'-(isopropylimino)diacetate, Diethyl 2,2'-(2,6-diethylphenylimino)diacetate, Diethyl 2,2'-(2,6-diisopropylphenylimino)diacetate, Diethyl 2,2'-(2-isopropylphenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(2,6-difluorophenylimino)diacetate, Diethyl 2,2'-(2,6-dibromo-4-methylphenylimino)diacetate, Diethyl 2,2'-(2,6-dichlorophenylimino)diacetate, Diethyl 2,2'-(4-bromo-2,6-diethylphenylimino)diacetate, Diethyl 2,2'-(2,6-dibromo-4-methoxyphenylimino)diacetate, Diethyl 2,2'-(2-methylcyclohexylimino)diacetate, di-n-butyl (2,6-di-tert-butylphenylimino) diacetate, Diethyl 2,2'-(2-para-methylphenyl-4,6-dimethylphenylimino)diacetate, diethyl 2,2'-(N-indan-1-ylimino)diacetate, Diethyl 2-(3,5-dimethylphenyl)-2,2'-(isopropylimino)diacetate, ethyl 2-(2-(ethoxycarbonyl)indolin-1-yl)acetate, bis(3,5-dimethyl-4-chlorophenyl) 2,2'-(2,6-diethylphenylimino) diacetate, Diethyl (2S,5S)-(N-isopropyl)-pyrrolidine-2,5-diformate, N-isopropyl-N-(2-ethoxy-2-ketoethyl)-alpha-amino-gamma-butyrolactone, ethyl alpha-(N-isopropyl-N-(1-(ethoxycarbonyl)cyclohexyl)amino)acetate, 4-(2,6-diethylphenyl)-2,6-dioxo-4-aza-l,7-dioxecan, Diethyl 2,2'-(para-(triethylsilyl)phenylimino)diacetate, Diethyl 2,2'-(meta-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-(ortho-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-((dimethylphenylsilyl)ethylimino)diacetate, and Bis(trimethylsilylmethyl) 2,2'-(isopropylimino)diacetate 37. The use according to any one of claims 33 to 36, selected from the group consisting of: <Claim 49> Formula (I) The compound of TIFF2025539733000046.tif4165, R in the formula 1 is one or more identical or different substituents R 8 is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 2 , R 3 , R 4 and R 5 is hydrogen, one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 6 and R 7 is one or more identical or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 1 ~R 9 may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings; However, the compound of formula (I) Dimethyl (3-bromophenylimino)diacetate, dimethyl 2,2'-(para-methylphenylimino)diacetate, bis(phenylmethyl) 2,2'-(2-bromoethylimino)diacetate, di-tert-butyl 2,2'-(2-bromoethylimino)diacetate, di-tert-butyl 2,2'-(benzylimino)diacetate, dibenzyl 2,2'-(2-bromoethylimino)diacetate, di-n-butyl 2,2'-(phenylimino)diacetate, dimethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(Phenylimino)diacetate, Dimethyl 2,2'-(Bromoethylimino)diacetate, Diisopropyl 2,2'-(para-methylphenylimino)diacetate, Dimethyl 2,2'-(n-Butylimino)diacetate, Dimethyl 2,2'-(n-Hexylimino)diacetate, Ethyl 2-[(2-ethoxy-2-oxoethyl)-methylamino]-4-methylpentanoate, N-(2-Bromoethyl)-N-[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-isoleucine 1,1-dimethylethyl ether N-(2-tert-butoxy-2-oxoethyl)-N-methylglycine ethyl ester, N-(2-bromoethyl)-N-[2-(1,1-dimethylethoxy)-2-oxoethyl]-L-phenylalanine 1,1-dimethylethyl ether, dimethyl 2,2'-(benzylimino)diacetate, diethyl 2,2'-(benzylimino)diacetate, N-(2-tert-butoxy-2-oxoethyl)-N-methylglycine ethyl ester, diethyl 2,2'-(2,5-dichlorophenylimino)diacetate, diethyl 2,2'-(5-bromo-2-methylphenylimino)diacetate, diethyl 2,2'-(5-iodophenylimino)diacetate diethyl 2,2'-(5-bromo-4-fluoro-2-methylphenylimino)diacetate, diethyl 2,2'-(5-bromo-4-fluoro-2-methylphenylimino)diacetate, methyl 2-((2-(tert-butoxy)-2-oxoethyl)(3-chlorophenyl)amino)propanoate, diethyl 2,2'-(n-hexylimino)diacetate, diethyl 2,2'-(n-octylimino)diacetate, di-tert-butyl 2,2'-(n-hexylimino)diacetate, dimethyl 2,2'-(chloroethylimino)diacetate, 1-methyl-azepan-2,The compound is not 7-dicarboxylic acid dimethyl ester, 1-benzyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, 1-methyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, N-Boc-α-allylproline methyl ester, N-Boc-methanoproline ethyl ester, N-benzyl-2,6-dicarbomethoxypiperidine, 1-para-chlorophenyl-2,5-pyrrolidinedicarboxylic acid diethyl ester, di-tert-butyl 2,2'-(methylimino)diacetate, dibenzyl 2,2'-diethyl-2,2'-(methylimino)diacetate, dibenzyl 2,2'-dibutyl-2,2'-(methylimino)diacetate, or di-tert-butyl 2,2'-diphenyl-2,2'-(methylimino)diacetate. <Claim 50> R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 9 Each of the C1-C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 teeth, C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl; C6~C 20Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 50. The compound according to claim 49, wherein the alkyl group is selected from the group consisting of straight chain or branched alkyl, more preferably C1 to C6 straight chain or branched alkyl. <Claim 51> R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 9 each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl). <Claim 52> R 2 , R 3 , R 4 , and R 5 50. The compound of claim 49, wherein each of is hydrogen. <Claim 53> The compound of formula (I) is represented by formula (II) TIFF2025539733000047.tif3164 compound, R in the formula 10 ,R 11 and R 12 is one or more identical or different substituents R 8independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, each R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 10 ~R 12 50. The compound of claim 49, wherein any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. <Claim 54> R 9 , R 10 , R 11 , and R 12 Each of C1~C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 teeth, C1~C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl; C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C20 Straight or branched alkyl, preferably C1-C 10 54. The compound of claim 53, wherein the alkyl group is selected from the group consisting of: straight chain or branched alkyl, more preferably C1 to C6 straight chain or branched alkyl. <Claim 55> R 9 , R 10 , R 11 , and R 12 each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 55. The compound of claim 54, wherein is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl). <Claim 56> The compound of formula (I) is represented by formula (III) TIFF2025539733000048.tif5067 compound, R in the formula 13 and R 14 is one or more of the same or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: R 15 and R 16 represents hydrogen, alkyl or cycloalkyl, optionally substituted aryl, halogen, -SiR 93 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 13 and R 14 may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings; R 28 is selected from the group consisting of hydrogen, -O-alkyl. <Claim 57> R 9 , R 13 , R 14 , R 15 , and R 16 Each of the C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10 aryl; R 8 teeth, C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1 to C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl; C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10linear or branched alkyl, more preferably C1-C6 linear or branched alkyl); R 28 is hydrogen and -O-alkyl (where alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 57. The compound according to claim 56, wherein the alkyl is selected from the group consisting of straight chain or branched alkyl, more preferably C1 to C6 straight chain or branched alkyl. <Claim 58> R 9 , R 13 , R 14 , R 15 , and R 16 each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl); R 28 is selected from the group consisting of hydrogen and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl. <Claim 59> R 15 and R 16 57. The compound of claim 56, wherein each of is independently a halogen, preferably selected from the group consisting of F, Cl, Br and I. <Claim 60> The compound of formula (I) is represented by formula (IV) TIFF2025539733000049.tif3864 compound, R in the formula 18 and R 19 is one or more of the same or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R 20 , R 21 , R 22 and R 23 is hydrogen, one or more of the same or different substituents R 8 independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with where R 8 represents alkyl, cycloalkyl, optionally substituted aryl, halogen, -O-alkyl, -SiR 9 3 independently selected from the group consisting of: where R 9 is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R 18 ~R 23 50. The compound of claim 49, wherein any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings. <Claim 61> R 9 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 Each of the C1~C 20 Straight or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl, and C6~C 20 Aryl, preferably C6-C 10aryl; and R is independently selected from the group consisting of 8 but, C1~C 20 Linear or branched alkyl, preferably C1-C 10 linear or branched alkyl, more preferably C1-C6 alkyl; C3~C 20 Cycloalkyl, preferably C3-C 10 cycloalkyl, more preferably C3-C6 cycloalkyl; C6~C 20 Aryl, preferably C6-C 10 aryl, and -O-alkyl (wherein alkyl is C1-C 20 Linear or branched alkyl, preferably C1-C 10 61. The compound of claim 60, wherein the alkyl group is selected from the group consisting of: straight chain or branched alkyl, more preferably C1 to C6 straight chain or branched alkyl. <Claim 62> R 9 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; 8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl). <Claim 63> R 20 , R 21 , R22 , and R 23 61. The compound of claim 60, wherein each of is hydrogen. <Claim 64> The compound of formula (I) Diethyl 2,2'-(isopropylimino)diacetate, Diethyl 2,2'-(2,6-diethylphenylimino)diacetate, Diethyl 2,2'-(2,6-diisopropylphenylimino)diacetate, Diethyl 2,2'-(2-isopropylphenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(2,6-difluorophenylimino)diacetate, Diethyl 2,2'-(2,6-dibromo-4-methylphenylimino)diacetate, Diethyl 2,2'-(2,6-dichlorophenylimino)diacetate, Diethyl 2,2'-(4-bromo-2,6-diethylphenylimino)diacetate, Diethyl 2,2'-(2,6-dibromo-4-methoxyphenylimino)diacetate, Diethyl 2,2'-(2-methylcyclohexylimino)diacetate, di-n-butyl (2,6-di-tert-butylphenylimino) diacetate, Diethyl 2,2'-(2-para-methylphenyl-4,6-dimethylphenylimino)diacetate, diethyl 2,2'-(N-indan-1-ylimino)diacetate, Diethyl 2-(3,5-dimethylphenyl)-2,2'-(isopropylimino)diacetate, ethyl 2-(2-(ethoxycarbonyl)indolin-1-yl)acetate, bis(3,5-dimethyl-4-chlorophenyl) 2,2'-(2,6-diethylphenylimino) diacetate, Diethyl (2S,5S)-(N-isopropyl)-pyrrolidine-2,5-diformate, N-isopropyl-N-(2-ethoxy-2-ketoethyl)-alpha-amino-gamma-butyrolactone, ethyl alpha-(N-isopropyl-N-(1-(ethoxycarbonyl)cyclohexyl)amino)acetate, 4-(2,6-diethylphenyl)-2,6-dioxo-4-aza-1,7-dioxecan, Diethyl 2,2'-(para-(triethylsilyl)phenylimino)diacetate, Diethyl 2,2'-(meta-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-(ortho-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-((dimethylphenylsilyl)ethylimino)diacetate, and Bis(trimethylsilylmethyl) 2,2'-(isopropylimino)diacetate 53. The compound according to any one of claims 49 to 52, selected from the group consisting of:

Claims

1. 1. A procatalyst for olefin polymerization comprising a titanium-containing compound, a magnesium-containing compound, a halogen, and an internal electron donor which is a compound of formula (I): The internal electron donor has the formula (I) is a compound of the formula R １ represents one or more identical or different substituents R ８ is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ２ , R ３ , R ４ and R ５ is hydrogen, one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ６ and R ７ represents one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １ ~R ９ may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

2. R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ９ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ 10. The procatalyst of claim 1, wherein the alkyl group is selected from the group consisting of: a straight chain or branched chain alkyl;

3. R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ９ is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; and R8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

4. R ２ , R ３ , R ４ and R ５ 10. The procatalyst of claim 1, wherein each of is independently hydrogen.

5. The internal electron donor is represented by formula (II) is a compound of the formula R １０ , R １１ and R １２ represents one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, each R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １０ ~R １２ Optionally, any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

6. R ９ , R １０ , R １１ , and R １２ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ is a straight or branched chain alkyl 6. The procatalyst of claim 5, independently selected from the group consisting of:

7. R ９ , R １０ , R １１ , and R １２ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; ８ 7. The procatalyst of claim 6, wherein is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

8. The internal electron donor is represented by formula (III) is a compound of the formula R １３ and R １４ is one or more of the same or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of R １５ and R １６ teeth, hydrogen, alkyl or cycloalkyl, optionally substituted aryl, halogen, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １３ and R １４ may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings; R ２８ 10. The procatalyst of claim 1, wherein is selected from the group consisting of hydrogen, -O-alkyl.

9. R ９ , R １３ , R １４ , R １５ , and R １６ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ is a straight chain or branched alkyl; R ２８ is hydrogen and —O-alkyl (where alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ straight-chain or branched alkyl) 9. The procatalyst of claim 8, wherein:

10. R ９ , R １３ , R １４ , R １５ , and R １６ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; ８ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and —O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; R ２８ 10. The procatalyst of claim 9, wherein is selected from the group consisting of hydrogen and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

11. R １５ and R １６ 9. The procatalyst of claim 8, wherein each of is independently a halogen, preferably selected from the group consisting of F, Cl, Br, and I.

12. The internal electron donor is represented by formula (IV): is a compound of the formula R １８ and R １９ is one or more of the same or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ２０ , R ２１ , R ２２ and R ２３ is hydrogen, one or more of the same or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １８ ~R ２３ Optionally, any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

13. R ９ , R １８ , R １９ , R ２０ , R ２１ , R ２２ , and R ２３ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ but, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ 13. The procatalyst of claim 12, wherein the alkyl group is selected from the group consisting of: a straight chain or branched chain alkyl;

14. R ９ , R １８ , R １９ , R ２０ , R ２１ , R ２２ , and R ２３ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; ８ 14. The procatalyst of claim 13, wherein is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

15. R ２０ , R ２１ , R ２２ and R ２３ 13. The procatalyst of claim 12, wherein each of is hydrogen.

16. The internal electron donor is diethyl 2,2'-(isopropylimino)diacetate, diethyl 2,2'-(2,6-diethylphenylimino)diacetate, diethyl 2,2'-(2,6-diisopropylphenylimino)diacetate, diethyl 2,2'-(2-isopropylphenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(2,6-difluorophenylimino)diacetate, diethyl 2,2'-(2,6-dibromo-4-methylphenylimino)diacetate, diethyl 2,2'-(2,6-dichlorophenylimino)diacetate, diethyl 2,2'-(4-bromo-2,6-diethylphenylimino)diacetate, diethyl 2,2'-(2,6-dibromo-4-methoxyphenylimino)diacetate, diethyl 2,2'-(2-methylcyclohexylimino)diacetate, di-n-butyl(2,6-di-tert-butylphenylimino)diacetate, diethyl 2,2'-(2-para-methylphenyl-4,6-dimethylphenylimino)diacetate, diethyl 2,2'-(N-indan-1-ylimino)diacetate, diethyl 2-(3,5-dimethylphenyl)-2,2'-(isopropylimino)diacetate, ethyl 2-(2-(ethoxycarbonyl)indolin-1-yl)acetate, bis(3,5-dimethyl-4-chlorophenyl)2,2'-(2,6-diethylphenylimino)diacetate, Diethyl (2S,5S)-(N-isopropyl)-pyrrolidine-2,5-diformate, N-isopropyl-N-(2-ethoxy-2-ketoethyl)-alpha-amino-gamma-butyrolactone, ethyl alpha-(N-isopropyl-N-(1-(ethoxycarbonyl)cyclohexyl)amino)acetate, 4-(2,6-diethylphenyl)-2,6-dioxo-4-aza-1,7-dioxecane, diethyl 2,2'-(para-(triethylsilyl)phenylimino)diacetate, diethyl 2,2'-(meta-(trimethylsilyl)phenylimino)diacetate, diethyl 2,2'-(ortho-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-((dimethylphenylsilyl)ethylimino)diacetate, and Bis(trimethylsilylmethyl) 2,2'-(isopropylimino)diacetate 16. The procatalyst of claim 15 selected from the group consisting of:

17. (a) contacting a magnesium-containing compound with a titanium-containing compound; (b) adding an internal electron donor to the mixture obtained in step (a), wherein the internal electron donor is a compound represented by formula (I): is a compound of the formula R １ represents one or more identical or different substituents R ８ is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ２ , R ３ , R ４ and R ５ is hydrogen, one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ６ and R ７ represents one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １ ~R ９ and wherein any of the above may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

18. (a) an olefin polymerization procatalyst according to any one of claims 1 to 16; (b) a cocatalyst, and (c) an external electron donor; 1. A catalyst system for olefin polymerization comprising:

19. 20. The catalyst system of claim 18, wherein the cocatalyst comprises an organoaluminum compound.

20. The organoaluminum compound is represented by the following formula: AlR ２４ ｍ X ３－ｍ 、 is a compound of During the ceremony, R ２４ is selected from hydrocarbon groups having 1 to 20 carbon atoms; 20. The catalyst system of claim 19, wherein X is a halogen atom and m is greater than 0 and less than or equal to 3.

21. 21. The catalyst system of claim 20, wherein the organoaluminum compound is selected from the group consisting of trialkylaluminums, trialkenylaluminums, dialkylaluminum halides, alkylaluminum sesquihalides, alkylaluminum dihalides, dialkylaluminum hydrides, and other partially hydrogenated alkylaluminums.

22. 22. The catalyst system of claim 21, wherein the organoaluminum compound is selected from the group consisting of triethylaluminum, triisobutylaluminum, tri-n-butylaluminum, tri-n-hexylaluminum, and tri-n-octylaluminum, triisoprenylaluminum, diethylaluminum chloride, dibutylaluminum chloride, and diethylaluminum bromide, ethylaluminum sesquichloride, butylaluminum sesquichloride, and ethylaluminum sesquibromide, ethylaluminum dichloride, n-propylaluminum dichloride, butylaluminum dibromide, diethylaluminum hydride, dibutylaluminum hydride, ethylaluminum dihydride, and n-propylaluminum dihydride.

23. 23. The catalyst system of any one of claims 19 to 22, wherein the organoaluminum compound is present in the catalyst system in an amount such that the molar ratio of aluminum to titanium present in the procatalyst is from about 0.1 to about 2000, preferably from about 5 to about 1000, more preferably from about 10 to about 700, and even more preferably from about 25 to about 400.

24. 24. The catalyst system according to any one of claims 18 to 23, wherein the external electron donor is selected from the group consisting of silicon compounds, ethers, esters, amines, and heterocyclic compounds.

25. The external donor has the formula: (R ２５ ) ａ (R ２６ ) ｂ Si(OR ２７ ) ｃ 、 is a compound of During the ceremony a and b are integers from 0 to 2, c is an integer from 1 to 4, and the sum (a+b+c) is 4; R ２５ , R ２６ , and R ２７ 25. The catalyst system according to any one of claims 18 to 24, wherein is a radical having 1 to 18 carbon atoms, which may contain heteroatoms.

26. a is 1, b is 1, c is 2, and R ２５ and R ２６ at least one of R is selected from a branched alkyl, cycloalkyl, or aryl group having 3 to 10 carbon atoms, which may contain heteroatoms; ２７ is C １ ~C １０ 26. The catalytic system of claim 25, wherein the alkyl group is preferably methyl.

27. 27. The catalyst system of claim 26, wherein the external electron donor is selected from the group consisting of methylcyclohexyldimethoxysilane, diphenyldimethoxysilane, methyl-t-butyldimethoxysilane, dicyclopentyldimethoxysilane, diisopropyldimethoxysilane, (2-ethylpiperidinyl)t-butyldimethoxysilane, (2-ethylpiperidinyl)thexyldimethoxysilane, (3,3,3-trifluoro-n-propyl)(2-ethylpiperidinyl)dimethoxysilane, methyl(3,3,3-trifluoro-n-propyl)dimethoxysilane, and N,N-diethylaminotriethoxysilane.

28. a is 0, c is 3, and R ２６ is a branched alkyl or cycloalkyl group which may contain heteroatoms, and R ２７ 26. The catalyst system of claim 25, wherein is methyl.

29. 26. The catalyst system of claim 25, wherein the external electron donor is selected from the group consisting of cyclohexyltrimethoxysilane, t-butyltrimethoxysilane, and hexyltrimethoxysilane.

30. 30. The catalyst system according to any one of claims 18 to 29, wherein the external electron donor is used in an amount such that the molar ratio between the cocatalyst and the external electron donor is from 0.1 to 500, preferably from 1 to 300, more preferably from 3 to 100.

31. A method for preparing a catalyst system for the polymerization of olefins, comprising contacting the procatalyst of any one of claims 1 to 16 with a cocatalyst and an external electron donor.

32. A process for the (co)polymerization of olefins, comprising contacting at least one olefin monomer with the catalyst system according to any one of claims 18 to 30.

33. as an internal electron donor in a catalyst for olefin polymerization The use of a compound of formula R １ represents one or more identical or different substituents R ８ is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ２ , R ３ , R ４ and R ５ is hydrogen, one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ６ and R ７ represents one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １ ~R ９ may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings.

34. R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ９ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ Aryl are independently selected from the group consisting of R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ straight-chain or branched alkyl) 34. The use according to claim 33, selected from the group consisting of:

35. R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ９ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; ８ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

36. R ２ , R ３ , R ４ , and R ５ 34. The use of claim 33, wherein each of is hydrogen.

37. The compound of formula (I) is represented by formula (II) is a compound of the formula R １０ , R １１ and R １２ represents one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, each R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １０ ~R １２ may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings.

38. R ９ , R １０ , R １１ and R １２ Each of the C １ -C ２０ Linear or branched alkyl, preferably C １ -C １０ Linear or branched alkyl, more preferably C １ -C ６ Alkyl, C ３ -C ２０ Cycloalkyl, preferably C ３ -C １０ Cycloalkyl, more preferably C ３ -C ６ cycloalkyl, and C ６ -C ２０ Aryl, preferably C ６ -C １０ Aryl are independently selected from the group consisting of R ８ but, C １ -C ２０ Linear or branched alkyl, preferably C １ -C １０ Linear or branched alkyl, more preferably C １ -C ６ Alkyl, C ３ -C ２０ Cycloalkyl, preferably C ３ -C １０ Cycloalkyl, more preferably C ３ -C ６ cycloalkyl, and C ６ -C ２０ Aryl, preferably C ６ -C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ straight-chain or branched alkyl) 38. The use according to claim 37, selected from the group consisting of:

39. R ９ , R １０ , R １１ , and R １２ is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; and R8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

40. The compound of formula (I) is a compound of formula (III) is a compound of the formula R １３ and R １４ is one or more of the same or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of R １５ and R １６ is hydrogen, alkyl or cycloalkyl, optionally substituted aryl, halogen, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １３ and R １４ may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings; R ２８ The use of claim 33, wherein is selected from the group consisting of hydrogen, -O-alkyl.

41. R ９ , R １３ , R １４ , R １５ , and R １６ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ linear or branched alkyl); R ２８ is hydrogen and —O-alkyl (where alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ 41. The use according to claim 40, wherein the alkyl group is selected from the group consisting of alkyl groups, which are straight chain or branched alkyl groups.

42. R ９ , R １３ , R １４ , R １５ , and R １６ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; ８ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and —O-alkyl (wherein alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl); R ２８ is selected from the group consisting of hydrogen and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

43. R １５ and R １６ 41. The use according to claim 40, wherein each of is independently a halogen, preferably selected from the group consisting of F, Cl, Br and I.

44. The compound of formula (I) is a compound of formula (IV) is a compound of the formula R １８ and R １９ is one or more of the same or different substituents R ８ R is independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with ２０ , R ２１ , R ２２ , and R ２３ is hydrogen, one or more of the same or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １８ ~R ２３ may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings.

45. R ９ , R １８ , R １９ , R ２０ , R ２１ , R ２２ , and R ２３ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ 45. The use according to claim 44, wherein the alkyl group is selected from the group consisting of: alkyl, straight chain or branched alkyl.

46. R ９ , R １８ , R １９ , R ２０ , R ２１ , R ２２ , and R ２３ is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; and R8 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

47. R ２０ , R ２１ , R ２２ , and R ２３ 45. The use of claim 44, wherein each of is hydrogen.

48. The compound of formula (I) is diethyl 2,2'-(isopropylimino)diacetate, diethyl 2,2'-(2,6-diethylphenylimino)diacetate, diethyl 2,2'-(2,6-diisopropylphenylimino)diacetate, diethyl 2,2'-(2-isopropylphenylimino)diacetate, diethyl 2,2'-(phenylimino)diacetate, diethyl 2,2'-(2,6-difluorophenylimino)diacetate, diethyl 2,2'-(2,6-dibromo-4-methylphenylimino)diacetate, diethyl 2,2'-(2,6-dichlorophenylimino)diacetate, diethyl 2,2'-(4-bromo-2,6-diethylphenylimino)diacetate, diethyl 2,2'-(2,6-dibromo-4-methoxyphenylimino)diacetate, diethyl 2,2'-(2-methylcyclohexylimino)diacetate, di-n-butyl(2,6-di-tert-butylphenylimino)diacetate, diethyl 2,2'-(2-para-methylphenyl-4,6-dimethylphenylimino)diacetate, diethyl 2,2'-(N-indan-1-ylimino)diacetate, diethyl 2-(3,5-dimethylphenyl)-2,2'-(isopropylimino)diacetate, ethyl 2-(2-(ethoxycarbonyl)indolin-1-yl)acetate, bis(3,5-dimethyl-4-chlorophenyl)2,2'-(2,6-diethylphenylimino)diacetate, Diethyl (2S,5S)-(N-isopropyl)-pyrrolidine-2,5-diformate, N-isopropyl-N-(2-ethoxy-2-ketoethyl)-alpha-amino-gamma-butyrolactone, ethyl alpha-(N-isopropyl-N-(1-(ethoxycarbonyl)cyclohexyl)amino)acetate, 4-(2,6-diethylphenyl)-2,6-dioxo-4-aza-1,7-dioxecane, diethyl 2,2'-(para-(triethylsilyl)phenylimino)diacetate, diethyl 2,2'-(meta-(trimethylsilyl)phenylimino)diacetate, diethyl 2,2'-(ortho-(trimethylsilyl)phenylimino)diacetate, Diethyl 2,2'-((dimethylphenylsilyl)ethylimino)diacetate, and Bis(trimethylsilylmethyl) 2,2'-(isopropylimino)diacetate The use according to any one of claims 33 to 36, selected from the group consisting of:

49. Formula (I) A compound of the formula: R １ represents one or more identical or different substituents R ８ is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ２ , R ３ , R ４ and R ５ is hydrogen, one or more identical or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R ６ and R ７ represents one or more identical or different substituents R ８ independently selected from the group consisting of cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １ ~R ９ may be linked together to form one or more saturated or unsaturated carbocyclic rings or saturated or unsaturated heterocyclic rings; However, the compound of formula (I) The compound is not bis(phenylmethyl) 2,2'-(2-bromoethylimino)diacetate, dibenzyl 2,2'-(2-bromoethylimino)diacetate, dibenzyl 2,2'-diethyl-2,2'-(methylimino)diacetate, or dibenzyl 2,2'-dibutyl-2,2'-(methylimino)diacetate.

50. R １ , R ２ , R ３ , R ４ , R ５ , and R ９ Each of the C １ -C ２０ Linear or branched alkyl, preferably C １ -C １０ Linear or branched alkyl, more preferably C １ -C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ６ and R ７ Each of the C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ 50. The compound of claim 49, wherein the alkyl is selected from the group consisting of: alkyl, alkyl substituted with alkyl, and alkyl substituted with ...

51. R １ , R ２ , R ３ , R ４ , R ５ , and R ９ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; ６ and R ７ each is independently selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; R ８ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

52. R ２ , R ３ , R ４ , and R ５ 50. The compound of claim 49, wherein each of is hydrogen.

53. The compound of formula (I) is represented by formula (II) is a compound of the formula R １０ represents one or more identical or different substituents R ８ is selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with R １１ and R １２ represents one or more identical or different substituents R ８ independently selected from the group consisting of cycloalkyl, aryl, optionally substituted with Here, each R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １０ ~R １２ 50. The compound of claim 49, wherein any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

54. R ９ and R １０ Each of C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R １１ and R １２ Each of C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ 54. The compound of claim 53, wherein the alkyl is selected from the group consisting of: alkyl, straight chain or branched.

55. R ９ and R １０ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; １１ and R １２ each is independently selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; R ８ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

56. The compound of formula (I) is a compound of formula (III) is a compound of In the formula R １３ and R １４ is one or more of the same or different substituents R ８ independently selected from the group consisting of cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of R １５ and R １６ is hydrogen, alkyl or cycloalkyl, optionally substituted aryl, halogen, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １３ and R １４ may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings; R ２８ 50. The compound of claim 49, wherein is selected from the group consisting of hydrogen, -O-alkyl.

57. R ９ , R １５ , and R １６ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R １３ and R １４ Each of the C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ teeth, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ is a straight chain or branched alkyl; R ２８ is hydrogen and —O-alkyl (where alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ 57. The compound of claim 56, wherein the alkyl is selected from the group consisting of: alkyl, alkyl substituted with ...

58. R ９ , R １５ , and R １６ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; １３ and R １４ each is independently selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; R ８ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and —O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl; R ２８ is selected from the group consisting of hydrogen and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

59. R １５ and R １６ 57. The compound of claim 56, wherein each of is independently a halogen, preferably selected from the group consisting of F, Cl, Br and I.

60. The compound of formula (I) is a compound of formula (IV) is a compound of In the formula R １８ and R １９ is one or more of the same or different substituents R ８ independently selected from the group consisting of cycloalkyl, aryl, optionally substituted with R ２０ , R ２１ , R ２２ and R ２３ is hydrogen, one or more of the same or different substituents R ８ independently selected from the group consisting of alkyl or cycloalkyl, aryl, optionally substituted with Here, R ８ is alkyl, cycloalkyl, optionally substituted aryl, halogen, —O-alkyl, —SiR ９ ３ are independently selected from the group consisting of Here, R ９ is independently selected from the group consisting of alkyl, cycloalkyl, and aryl; R １８ ~R ２３ 50. The compound of claim 49, wherein any of may be linked together to form one or more saturated or unsaturated carbocyclic or saturated or unsaturated heterocyclic rings.

61. R ９ , R ２０ , R ２１ , R ２２ , and R ２３ Each of the C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; and R １８ and R １９ Each of the C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, and C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl; R ８ but, C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ Alkyl, C ３ ~C ２０ Cycloalkyl, preferably C ３ ~C １０ Cycloalkyl, more preferably C ３ ~C ６ cycloalkyl, C ６ ~C ２０ Aryl, preferably C ６ ~C １０ aryl, and -O-alkyl (wherein alkyl is C １ ~C ２０ Linear or branched alkyl, preferably C １ ~C １０ Linear or branched alkyl, more preferably C １ ~C ６ 61. The compound of claim 60, wherein the alkyl is selected from the group consisting of: alkyl, alkyl aryl, alkyl ether, alkyl ethers ...

62. R ９ , R ２０ , R ２１ , R ２２ , and R ２３ each is independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; １８ R １９ each is independently selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and phenyl; R ８ is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, and -O-alkyl, where alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl.

63. R ２０ , R ２１ , R ２２ , and R ２３ 61. The compound of claim 60, wherein each of is hydrogen.

64. The compound of formula (I) Bis(3,5-dimethyl-4-chlorophenyl) 2,2'-(2,6-diethylphenylimino) diacetate, and Bis(trimethylsilylmethyl) 2,2'-(isopropylimino)diacetate 53. The compound of any one of claims 49 to 52, selected from the group consisting of:

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