KR20220022349A - (ALKYL)ARENES AND A Method for Producing the Same - Google Patents

Abstract

The present invention relates to an alkylarene compound prepared through the Friedel-Crafts alkylation reaction and a method for preparing the same. The alkylarene compound is represented by chemical formula 3, wherein R^1 represents a C1-C10 alkyl group or (CH_2)_qSi(R^3)_p(OR^4)_3-p (wherein q = 1-10, R^3 = Cl or CH_3, p = 0, 1, 2, 3, and R^4 = CH_3 or C_2H_5); n = 0, 1, 2 or 3; Ar = benzene, naphthalene, anthracene, biphenyl, terpenylene, anthrone, anthraquinone, pyrene, phenanthrancene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, thioanisole, tetracene, pentacene or an aromatic compound having 1-8 rings; R^2 represents a C1-C8 alkyl group or phenyl group-containing alkyl group; l = 0, 1, 2, 3, or 4; and m = 1, 2 or 3. According to the present invention, the alkylarene compound is prepared by using a basic organic phosphine catalyst as a catalyst through the Friedel-Crafts alkylation reaction with no limitation caused by the use of a Lewis acid as a catalyst.

Description

Alkyl arene compound and its manufacturing method {(ALKYL) ARENES AND A Method for Producing the Same}

The present invention relates to an alkyl arene compound synthesized by Friedel-Crafts alkylation reaction and a method for preparing the same, and specifically, to an alkyl arene compound synthesized by Friedel-Crafts alkylation reaction of an alkyl halide compound and an aromatic compound using an organophosphine compound as a catalyst, and It relates to a manufacturing method thereof.

Friedel-Crafts alkylation, which introduces organic substituents into aromatic compounds, is a very important reaction in organic synthesis and has been widely used for over a century (Roberts, Royston M; Khalaf, Ali, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, Inc., New York, New York, USA, 1984 ). This Friedel-Crafts reaction is known to necessarily require a Lewis acid catalyst, and inorganic chlorides such as aluminum, boron, and iron are used. Friedel-Crafts alkylation reaction is a step in which a Lewis acid, such as boron trichloride or aluminum trichloride, which is a catalyst, attracts a halide of an alkyl halide compound, and a boron or aluminum tetrachloride anion is generated to form an alkyl cation to form an arene with high electron density. It consists of a step of alkylation by an electrophilic substitution reaction. However, when a starting material with many phenyl groups is used or when a product has many phenyl groups, the Lewis acid easily coordinates with them, so it is not easy to remove it from the reactant after the reaction. Therefore, it is known that when benzene is synthesized with benzyl chloride and diphenylmethane by the Friedel-Crafts alkylation reaction, acidic silica, an inorganic solid, is used as a carrier for the Lewis acid catalyst, and the catalyst can be easily removed after the reaction (Selvaraj, M.; Lee). , TG Journal of Molecular Catalysis A: Chemical 2006 , 243(2) , 176-182). A Lewis acid catalyst easily forms a coordination bond with an anthracene having three benzene rings or an aromatic compound with more benzene rings than that of an aromatic compound to introduce an organic group, so that the activity of the catalyst is greatly reduced. . Therefore, in order to introduce an organic substituent by reacting anthracene or an aromatic compound having more benzene rings with allyl halide, benzyl halide or alkyl halide, a neutral or basic compound should be used as a catalyst instead of an acid catalyst. Neutral catalysts suitable for this Friedel-Crafts alkylation are not well known. On the other hand, using organophosphonium chloride as a catalyst, the alkyl halide and trichlorosilane are reacted to remove the halogen from the alkyl halide, hydrogen is taken from the trichlorosilane to generate hydrogen halide, and the alkyl group is silane through the dehydrohalogenation Si-C bonding reaction. The synthesis of alkylchlorosilanes substituted with is known (Yeon Seok Cho, YS; Kang, S.-H.; Han, JS; Yoo, BR; Jung, IN, J. Am. Chem. Soc. 2001 , 123 , 5584). As disclosed in the prior art above, organophosphonium chloride used as a catalyst in the synthesis of alkylchlorosilane in which an alkyl halide and trichlorosilane are reacted to substitute an alkyl group to silane by a dehydrohalogenation Si-C bond reaction is neutral. become organic salts. Also, the tertiary trialkylphosphine corresponds to a Lewis base, not a Lewis acid. When such organophosphonium chloride is used for the reaction of an aromatic compound and an alkyl halide compound, a Friedel-Crafts alkylation reaction, which is a dehydrohalogenation CC bonding reaction that takes halogen from the alkyl halide compound and removes hydrogen from the aromatic ring to generate HX, can be induced. there is. In addition, since the organophosphonium chloride catalyst has different physical properties from the reactant or product, it is easy to recover and can be reused. For example, using trialkylphosphine or organophosphonium halide as a catalyst to induce Friedel-Crafts alkylation reaction of allyl chloride or benzyl chloride to an arene compound, it is very economical and produces an allyl arene compound and a benzyl arene compound in high yield, respectively will be possible The allyl halide or benzyl halide compound used in Friedel-Crafts alkylation has great activity because the halogen-substituted methylene group is substituted with a functional group such as a vinyl group or a phenyl group, so that the halogen is dropped and the generated cations are stabilized. Therefore, it is possible to synthesize an alkylarene compound by Friedel-Crafts alkylation reaction without a functional group directly bonded to a halogen-substituted methylene group, and a compound based thereon and a preparation method thereof are an object of the present invention.

Prior Art 1: Roberts, Royston M; Khalaf, Ali, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, Inc., New York, New York, USA, 1984 Prior art 2: Selvaraj, M.; Lee, T. G. Journal of Molecular Catalysis A: Chemical 2006, 243(2), 176-182 Prior Art 3: Yeon Seok Cho, Y. S.; Kang, S.-H.; Han, J. S.; Yoo, B. R.; Jung, I. N., and J. Am. Chem. Soc. 2001, 123, 5584

It is an object of the present invention to provide an alkylarene compound synthesized by reacting an alkyl halide compound with an aromatic compound using an organophosphine compound as a catalyst and a method for preparing the same.

According to a suitable embodiment of the present invention, the alkylarene compound is represented by Formula 3,

Formula 3:

wherein R ¹ = an alkyl group having 1 to 10 carbon atoms or (CH ₂ ) _q Si(R ³ ) _p (OR ⁴ ) _3-p (q=1-10, R ³ = Cl or CH ₃ , p=0, 1, 2, 3, R ⁴ =CH ₃ or C ₂ H ₅ ); n = 0, 1, 2 or 3; Ar = benzene, naphthalene, anthracene, biphenyl, terphenylene, anthrone, anthraquinone, pyrene, phenanthrene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, anisole, thioani sol, tetracene, pentacene and aromatic compounds having 1 to 8 rings; R ² = an alkyl group having 1 to 8 carbon atoms or an alkyl group including a phenyl group; l = 0, 1, 2, 3 or 4; and m = 1, 2 or 3.

= 메틸, 에틸, 프로필, 아이소프로필, 부틸, 펜틸, 헥실, 헵틸, 옥틸, 노닐, 데실, sec-부틸, 트리메틸실릴메틸, 트리클로로실릴메틸, 트리메톡시실릴메틸, 트리에톡시실릴메틸, 메틸다이클로로실릴메틸, 메틸다이메톡시실릴메틸, 다이메틸클로로실릴메틸, 다이메틸메톡시실릴메틸, 다이메틸에톡시실릴메틸, 트리클로로실릴에틸, 트리메톡시실릴에틸, 트리에토시실릴에틸, 트리크로로실릴프로필, 트리메톡시실릴프로필, 트리에톡시실릴프로필, 트리클로로실릴헥실, 트리메톡시실릴헥실, 트리에톡시실릴헥실; R²= CH₃ 또는 C₂H₅; m=1,2 또는 3; 그리고 l= 0, 1 또는 2가 된다. According to another suitable embodiment of the present invention, in Formula 3, Ar = anthracene, biphenyl, terphenylene, anthrone, anthraquinone, pyrene, phenanthrcene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, anisole, thioanisole, tetracene or pentacene;

= methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, sec-butyl, trimethylsilylmethyl, trichlorosilylmethyl, trimethoxysilylmethyl, triethoxysilylmethyl, methyl Dichlorosilylmethyl, methyldimethoxysilylmethyl, dimethylchlorosilylmethyl, dimethylmethoxysilylmethyl, dimethylethoxysilylmethyl, trichlorosilylethyl, trimethoxysilylethyl, triethoxysilylethyl, tri chlorosilylpropyl, trimethoxysilylpropyl, triethoxysilylpropyl, trichlorosilylhexyl, trimethoxysilylhexyl, triethoxysilylhexyl; R ² =CH ₃ or C ₂ H ₅ ; m=1,2 or 3; and l = 0, 1 or 2.

According to another suitable embodiment of the present invention, in the method for preparing an alkylarene compound, a compound represented by Formula 3 is prepared by reacting the compounds represented by Formulas 1 and 2 with an organophosphine compound as a catalyst,

Formula 1:

Formula 2:

Formula 3:

In Formulas 1, 2 and 3, R ¹ = an alkyl group having 1 to 10 carbon atoms or (CH ₂ ) _q Si(R ³ ) _p (OR ⁴ ) _3-p (q=1-10, R ³ = Cl or CH ₃ , p=0, 1, 2, 3, R ⁴ =CH ₃ or C ₂ H ₅ ); n=0, 1, 2 or 3; X=Cl, Br or I; Ar = benzene, naphthalene, anthracene, biphenyl, terphenylene, anthrone, anthraquinone, pyrene, phenanthrene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, anisole, thioani sol, tetracene, pentacene and aromatic compounds having 1 to 8 rings; R ² = H an alkyl group having 1 to 8 carbon atoms or an alkyl group including a phenyl group; l = 0, 1, 2, 3 or 4; and m = 1, 2 or 3.

According to another suitable embodiment of the present invention, the molar ratio of the reaction of the compound represented by Formula 1 to the compound represented by Formula 2 is 6:1 to 1:3.

According to another suitable embodiment of the present invention, the compound represented by Formula 4 is used as a catalyst,

Formula 4:

P(R") ₃ ,

In the above, R" includes an alkyl group having 1 to 12 carbon atoms or a phenyl group that is alkenyl, and different R" is a cyclic structure connected by a covalent bond.

According to another suitable embodiment of the present invention, the compound represented by Formula 5 is used as a catalyst,

Formula 5:

P(R") ₄ X'

In the above, R" contains a phenyl group that is an alkyl group having 1 to 12 carbon atoms or an alkenyl group, and different R" becomes a cyclic structure connected by a covalent bond, and X'=Cl, Br, or I is one selected from .

According to another suitable embodiment of the present invention, the compound represented by Formula 6 is used as a catalyst,

Formula 6:

X'(R") ₃ PYP(R") ₃ X

In the above, R″ includes a phenyl group having 1 to 12 carbon atoms or an alkenyl group, and different R″ are cyclic structures connected by a covalent bond, X′=Cl, Br or I, and Y=C1 It becomes an alkyl group of ∼12, an alkyl group including an aromatic group, or an aromatic group.

According to another suitable embodiment of the present invention, the concentration of the catalyst used in the method for preparing the alkylarene compound is 5 to 20 mol% based on the compound of formula (1).

According to another suitable embodiment of the present invention, the reaction temperature in the production method of the alkylarene compound is 100 ~ 250 ℃.

According to another suitable embodiment of the present invention, in the method for preparing an alkylarene compound, the reaction solvent is at least one selected from the group consisting of hydrocarbons, ethers, dimethoxyethane (DME) and THF.

According to another suitable embodiment of the present invention, when the compound of Formula 1 and the compound of Formula 2 are liquid, the alkylarene compound is produced by reacting without a solvent.

The method for producing an alkyl arene compound according to the present invention uses a neutral or basic organophosphine catalyst rather than a metal compound to synthesize an alkyl arene by reaction of an alkyl halide compound with an aromatic compound, and a Lewis acid is used as a catalyst. It allows the Friedel-Crafts alkylation reaction to proceed easily without limitation. In general, in the case of Friedel-Crafts alkylation, the catalyst is a Lewis acid catalyst and becomes a metal chloride such as aluminum, boron, iron, copper, etc., and such a catalyst has a disadvantage in that it is difficult to separate and reuse it from the reactants after the reaction. In addition, when anthracene or an aromatic compound having more benzene rings than that is used, the catalyst easily forms a complex with them, and the activity is lowered, so that it is difficult to smoothly perform the alkylation reaction. The method for producing an alkyl arene using an organophosphine catalyst according to the present invention makes it possible to solve such a problem. The catalyst compound group used in the preparation method according to the present invention may be a tertiary organophosphorus compound or a quaternary organophosphonium salt of Group 5 among organic substances. When a quaternary organophosphonium salt is used as a catalyst to react an alkyl chloride with a chlorosilane having a Si-H bond, various alkylsilanes can be synthesized by a dehydrohalogenation Si-C bond reaction. Accordingly, these catalysts can act very effectively in the process of synthesizing alkylarenes by the C-C bond reaction of hydrogen halide, and have the advantage that the catalyst can be easily recovered and recycled. Arene compounds have been used very limitedly as electronic materials because of their low reactivity and low solubility in organic solvents. However, the alkylarene compound according to the present invention can have fluorescence while increasing solubility in organic solvents by directly reacting an organic silicon or an organic-inorganic binder with an anthracene having fluorescence or an aromatic compound having more benzene rings than that. . In addition, the alkylarene compound has improved adhesion, so it can be usefully applied to electronic materials as a new functional silicone product.

Hereinafter, the present invention will be described in detail with reference to Examples, but the Examples are for a clear understanding of the present invention, and the present invention is not limited thereto.

In the method for preparing an alkylarene compound according to the present invention, the compound represented by Formula 3 is produced by reacting the compound represented by Formulas 1 and 2 with an organophosphine compound as a catalyst.

Formula 1:

Formula 2:

Formula 3:

wherein R ¹ = an alkyl group having 1 to 10 carbon atoms or (CH ₂ ) _q Si(R ³ ) _p (OR ⁴ ) _3-p (q=1-10, R ³ = Cl or CH ₃ , p=0, 1, 2, 3, R ⁴ =CH ₃ or C ₂ H ₅ ); n=0, 1, 2 or 3; X=Cl, Br or I; Ar = benzene, naphthalene, anthracene, biphenyl, terphenylene, anthrone, anthraquinone, pyrene, phenanthrene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, anisole, thioani sol, tetracene, pentacene or aromatic compounds having 1 to 8 rings; R ² = H, an alkyl group having 1 to 8 carbon atoms or an alkyl group including a phenyl group; l = 0, 1, 2, 3 or 4; and m = 1, 2 or 3.

Scheme 1

In Scheme 1, the catalyst may be a tertiary organophosphine or a quaternary organophosphonium salt, and dehydrohalogenation CC that takes a halogen from the alkyl halide compound of Formula 1 and subtracts hydrogen from the aromatic ring of Formula 2 to generate HX The alkylarene compound represented by Formula 3 may be produced through the coupling reaction.

The tertiary organophosphine used as a catalyst in Scheme 1 may be represented by Formula 4 below, and the quaternary organophosphine salt may be represented by Formula 5 or Formula 6.

Formula 4:

P(R") ₃ ,

In the above, R″ may include a phenyl group having 1 to 12 carbon atoms or an alkenyl group. Two R″ may be connected to each other by a covalent bond to have a cyclic structure, and each R″ may be the same as or Or it may have a different structure.

Formula 5:

P(R") ₄ X',

In the above, X′=Cl, Br, or I, R″ is the same as the compound of Formula 4, R″ may be covalently linked to each other to have a cyclic structure, and each R″ is the same as or different from each other can have a structure.

Formula 6:

X'(R") ₃ PYP(R") ₃ X',

In the above, X' and R" are the same as in the compound of Formula 5, respectively, and Y = may be an alkyl group or an aromatic group having 1 to 12 carbons or an alkyl group or an aromatic group, and two R" are connected to each other by a covalent bond to form a cyclic structure may have, and each R" may have the same or different structure from each other.

The tertiary organophosphine as a catalyst is trimethylphosphine, triethylphosphine, tributylphosphine, methyldiphenylphosphine, tricyclohexylphosphine, triisopropylphosphine, tripropylphosphine, dimethylphenylphosphine , ethyldiphenylphosphine, t-butyldiphenylphosphine, t-butyldiisopropyl, isopropyldiphenylphosphine, dicyclohexylphenylphosphine, benzyldiphenylphosphine, cyclohexyldiphenylphosphine, tri at least one compound selected from the group consisting of cyclopentylphosphine, di-t-butylneopentylphosphine, di-t-butylphenylphosphine, di-t-butylmethylphosphine and t-butyldicyclohexylphosphine may include

Quaternary organophosphonium salts include benzyltributylphosphonium chloride, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, tetrabutylphosphonium iodine, tetramethylphosphonium bromide, tetraethylphosphonium chloride, (4-ethylbenzyl) Triphenylphosphonium chloride, hexyltriphenylphosphonium chloride, benzyltriphenylphosphonium chloride, tetraphenylphosphonium chloride, bis(benzyldimethylphosphonium chloride)ethane, bis(benzyldimethylphosphonium chloride)butane or silica or silicone resin , silicon silsesquioxene and at least one compound selected from the group consisting of quaternary alkylphosphonium chloride immobilized on an organic polymer.

Since the boiling point of the alkyl halide compound of Formula 1 or the aromatic compound of Formula 2 and the solvent used in the manufacturing process of the alkylarene compound is lower than the reaction temperature of 250° C. There is a need. After preparing the alkyl halide compound of Formula 1 and the aromatic compound of Formula 2, the tertiary organophosphine or quaternary organophosphonium salt used as a catalyst is added in an amount of 5 to 20 mol% based on Formula 1 and mixed. Then, when the reaction mixture is heated to 100 to 250 °C, preferably 150 to 220 °C, an alkylarene compound such as Chemical Formula 3 according to Scheme 1 can be synthesized. In this process, the tertiary organophosphine used as a catalyst reacts with an alkyl halide compound during the reaction to become a quaternary organophosphine halide salt. In addition, the quaternary organophosphonium salt used as a catalyst is easily recovered from the reaction mixture, and for example, if the reaction product is distilled under reduced pressure after completion of the reaction, the catalyst remains without distillation and can be simply recovered. The catalyst can be recovered to a level of 80% of the amount initially used, and the recovered catalyst can be recrystallized with an appropriate solvent and reused.

According to one embodiment of the present invention, in the synthesis process of alkylarene, the alkyl halide compound of Formula 1 and the aromatic compound of Formula 2 are put under a nitrogen atmosphere, and a tertiary organophosphine or quaternary organophosphonium salt catalyst is subjected to pressure. After being put into a reaction tank made of a stainless tube, the stopper is closed and the reaction is performed by heating to the reaction temperature. In this process, the alkyl halide compound of Formula 1 and the aromatic compound of Formula 2 may be mixed in a molar ratio of 6:1 to 1:3, and if it is necessary to introduce several moles of an alkyl group into the aromatic compound, The ratio of the alkyl halide compound may increase, so that the reaction may proceed. The tertiary organophosphine represented by Chemical Formula 4 or the quaternary organophosphonium salt catalyst of Chemical Formulas 5 and 6 may be 5 to 20 mol% based on Chemical Formula 1. In this process, the reaction solvent may be, for example, a reaction solvent such as an aliphatic hydrocarbon, or a solvent such as ether, dimethoxyethane (DME) or THF, depending on the reactant. When such a reaction solvent is used, the reactants can be uniformly distributed. In particular, when THF is used, the ring is opened by HX, which is a by-product, and halobutyl alcohol is produced. Phosphorus HX gas can be removed. However, when using the material of Formula 1 containing alkoxysilane or chlorosilane, it is not suitable to use THF as a solvent because it may be hydrolyzed by a by-product by THF or Si-Cl may be substituted with halobutoxy. If ether with a low boiling point is used as a solvent, it vaporizes at a reaction temperature of 200° C., so the pressure of the reactor is increased and the risk of explosion may increase. On the other hand, if the compounds of Formulas 1 and 2 are both liquid or compatible with each other, the reaction may be performed without using a solvent. The reaction temperature may be 100 to 250 °C, preferably 150 to 220 °C. After reacting for 1 to 48 hours under such conditions, when the reaction is completed, the stopper is opened to discharge the generated hydrogen halide, and the product is separated by distillation or recrystallization under normal or reduced pressure to obtain the desired product. As described above, it is possible to separate and recycle the catalyst after manufacturing the product. When a tertiary organophosphine is used instead of a quaternary phosphonium salt as a catalyst, it reacts with an alkyl halide compound during the reaction to become a quaternary phosphonium salt, so the catalyst can be separated from the product and used again without any difficulty. The quaternary organophosphonium salt, which is a catalyst, can be recovered and reused up to 80%, which is economically very advantageous. If the organic phosphonium salt is immobilized on a silicone resin, silica, or zeolite, it is very convenient to recover and reuse it after the reaction.

The alkyl halide compound of Formula 1 for the reaction is methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, ethyl iodide, 1-chloropropane, 1-bromopropane, 1-iodopropane, 2 -Chloropropane, 2-bromopropane, 2-iodopropane, 1-chlorobutal, 1-bromobutane, 1-iodobutane, 2-chlorobutane, 2-bromobutane, 2-iodobutane, t-Butyl chloride, t-butyl bromide, t-butyl iodide, 1-chloropentane, 1-bromopentane, 1-iodopentane, 2-chloropentane, 2-bromopentane, 2-iodo Pentane, 1-chlorohexane, 1-bromohexane, 1-iodohexane, 2-chlorohexane, 2-bromohexane, 2-iodohexane, 3-chlorohexane, 3-bromohexane, 3-io Dohexane, 1-chloroheptane, 1-bromoheptane, 1-iodoheptane, 2-chloroheptane, 2-bromoheptane, 2-iodoheptane, 1-chlorooctane, 1-bromooctane, 1- Iodooctane, 1-chlorononane, 1-bromononane, 1-iodononane, 1-chlorodecane, 1-bromodecane, 1-iododecane, (chloromethyl)trichlorosilane, (chloromethyl) Methyldichlorosilane, (chloromethyl)dimethylchlorosilane, (chloromethyl)trimethylsilane, (chloromethyl)trimethoxysilane, (chloromethyl)triethoxysilane, (chloromethyl)methyldimethoxysilane, ( Chloromethyl) methyldiethoxysilane, (chloromethyl)dimethylmethoxysilane, (chloromethyl)dimethylethoxysilane, 2-chloroethyltrichlorosilane, 2-chloroethyltrimethoxysilane, 2-chloroethyl Triethoxysilane, 3-chloropropyltrichlorosilane, 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 6-chlorohexyltrichlorosilane, 6-chlorohexyltrimethoxysilane and 6- It may be at least one compound selected from the group consisting of chlorohexyltriethoxysilane. All of these compounds correspond to commercially produced substances or compounds whose synthesis methods are known in the literature.

The compound represented by Formula 2 corresponds to a compound that can be obtained commercially or can be synthesized, and includes benzene, toluene, o-xylene, m-xylene, p-xylene, mesitylene, ethylbenzene, propylbenzene, n-butylbenzene, isobutylbenzene, t-butylbenzene, 1,2,4,5-tetramethylbenzene, fluorobenzene, bromobenzene, iodobenzene, anisole, thioanisole, biphenyl, flu Orene, o-terphenylene, m-terphenylene, p-terphenylene, naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 1-methyl-2-methylnaphthalene, biphenyl ether, biphenyl sulfide, anthracene , 9-bromoanthracene, 9-methylanthracene, 9,10-dimethylanthracene, anthrone, pyrene, 1,6-dimethylpyrene, 2,7-dimethylpyrene, 1,6-diphenylpyrene, 2,7- at least one compound selected from the group consisting of dibenzylpyrene, 2,7-bis(diphenylmethyl)pyrene, perylene, dimethylperylene, tetracene, and pentacene.

Since the alkyl halide compound of Formula 1 may be substituted as much as the number of hydrogens bonded to the benzene ring of the aromatic compound of Formula 2, various types of products may be obtained depending on the reaction molar ratio. When the alkyl halide compound of Formula 1 is used in excess, that is, when the compounds of Formula 1 and Formula 2 are reacted in a molar ratio of 6:1, a plurality of alkyls may be substituted in the aromatic compound of Formula 2, and the aromatic compound of Formula 2 may be substituted. When the compound is used in excess relative to the alkyl halide compound, that is, when the compounds of Formulas 1 and 2 are reacted in a molar ratio of 1:3, a compound in which one alkyl is substituted can be obtained as a main product. Hereinafter, examples in which specific methods and conditions for the production of Chemical Formula 3 according to the present invention are described will be described.

The following examples are illustrative and the present invention is not limited thereto.

Example

Example 1: Synthesis of 1-isopropyl-2-methylnaphthalene

50 g (0.35 mol) of 1-methylnaphthalene and 13.8 g (0.18 mol) of 2-chloropropane, 2.5 g of dimethylphenylphosphine corresponding to 10% of the moles of 2-chloropropane in a high-temperature, high-pressure reactor with 290 ml stainless steel tube ( 0.018 mol) and 50 ml of THF were added and reacted at 230° C. for 6 hours. The solution was taken out in a round-bottom flask, and 18.2 g (0.10 mol, yield 55%) of the product was obtained through distillation under reduced pressure. As a result of the analysis of 300 MHz hydrogen nuclear magnetic resonance, the obtained product was C-CH ₃ at 1.31 ppm (d, 6H), C- CH ₃ at 2.62 ppm (s, 3H), C - CH at 2.88 ppm (s, 1H), Naph- H was confirmed at 6.9-7.9 ppm (m, 6H).

Example 2: Synthesis of 1-butylnaphthalene

In the same manner as in Example 1, 50 g (0.39 mol) of naphthalene, 26.7 g (0.20 mol) of 1-bromobutane, 3.9 g (0.02 mol) of tributylphosphine, and 50 ml of THF were added, and reacted at 230° C. for 6 hours to produce a product 17.3 g (0.09 mol, yield 47%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH ₃ at 0.89 ppm (t, 3H), C- CH ₂ -C at 1.30 ppm (m, 2H), Naph-CC at 1.55 ppm (m, 2H) H ₂ , Naph-C H ₂ at 3.07 ppm (t, 2H), and Naph-C H ₂ at 6.98-8.08 ppm (m, 7H) were identified.

Example 3: Synthesis of 9-(t-butyl)-10-methylanthracene

In the same manner as in Example 1, 50 g (0.26 mol) of 9-methylanthracene, 12 g (0.13 mol) of t-butyl chloride, 3.6 g (0.013 mol) of tricyclohexylphosphine, and 50 ml of THF were added and reacted at 230°C for 6 hours. 18.1 g (0.07 mol, yield 56%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Anth-C- CH ₃ at 1.48 ppm (s, 9H), Anth- CH ₃ at 2.72 ppm (s, 3H), Anth at 7.40-8.20 ppm (m, 8H) - H was confirmed.

Example 4: Synthesis of 1,5-bis(isobutyl)naphthalene

In the same manner as in Example 1, 30 g (0.23 mol) of naphthalene, 55.2 g (0.7 mol) of isobutyl chloride, 8.9 g (0.03 mol) of tetrabutylphosphonium chloride, and 50 ml of THF were added and reacted at 230 ° C. for 6 hours to produce 28.3 g (0.13 mol, yield 58%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH ₃ at 1.3ppm (d, 12H), Naph- CH at 2.9ppm (m, 2H), and Naph- H at 7.0-7.9ppm (m, 6H). Confirmed.

Example 5: Synthesis of ((4-hexylphenyl)phenyl)sulfide

In the same manner as in Example 1, 50 g (0.268 mol) of biphenyl sulfide, 16.1 g (0.134 mol) of 1-chlorohexane, 4 g (0.0134 mol) of tetrabutylphosphonium chloride and 50 ml of THF were added and reacted at 230 ° C. for 6 hours. 4.2 g (0.163 mol, yield 61%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH ₃ at 0.88 ppm (t, 3H), C- CH ₂ -C at 1.31 ppm (m, 6H), Ph-C at 1.58 ppm (m, 2H) -CH 2 , Ph-C-CH ₂ at _2.64ppm (t, 2H), Ph- H at 7.00-7.52ppm (m, 9H) was confirmed.

Example 6: Synthesis of 4-(2-hexyl)-1,1′-biphenyl

In the same manner as in Example 1, 50 g (0.324 mol) of biphenyl, 19.55 g (0.162 mol) of 2-chlorohexane, 3.3 g (0.0162 mol) of tributylphosphine, and 50 ml of THF were added and reacted at 230° C. for 6 hours to produce a product 35.5 g (0.149 mol, yield 46%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C-CH _{3 at 0.88 ppm (t, 3H), Ph-C-CH 3} at _1.16 ppm (d, 3H), C - CH at 1.31 ppm (m, 4H) ₂ -C, Ph-C- CH ₂ at 1.54ppm (m, 2H), Ph- CH at 2.55ppm (s, 1H), and Ph- H at 7.38-7.75ppm (m, 9H) were identified.

Example 7: Synthesis of 6-octylpentacene

In the same manner as in Example 1, 50 g (0.18 mol) of pentacene, 13.4 g (0.09 mol) of 1-bromooctane, 1 g (0.009 mol) of triethylphosphine, and 50 ml of THF were added and reacted at 230° C. for 6 hours to produce a product 20.2 g (0.06 mol, yield 62%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH ₃ at 0.88 ppm (t, 3H), C- CH ₂ -C at 1.31 ppm (m, 10H), and Pentacene-C at 1.61 ppm (m, 2H). - CH ₂ , Pentacene- CH ₂ at 3.07 ppm (t, 2H), and Pentacene H at 7.54-8.25 ppm (m, 13H) were confirmed.

Example 8: Synthesis of 1-isopropylnaphthalene

In the same manner as in Example 1, 50 g (0.39 mol) of naphthalene, 15.3 g (0.195 mol) of 2-chloropropane, 5.5 g (0.0195 mol) of tricyclohexylphosphine, and 50 ml of THF were added, and reacted at 230° C. for 6 hours to produce a product 16.6 g (0.10 mol, yield 50%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH ₃ at 1.31 ppm (d, 6H), Naph- CH at 2.28 ppm (m, 1H), and Naph- H at 6.98-8.08 ppm (m, 7H). Confirmed.

Example 9: Synthesis of 2-(t-butyl)pyrene

In the same manner as in Example 1, 50 g (0.247 mol) of pyrene, 11.4 g (0.12 mol) of t-butyl chloride, 3.6 g (0.012 mol) of tetrabutylphosphonium chloride, and 50 ml of THF were added and reacted at 230° C. for 6 hours to produce a product 17.4 g (0.07 mol, yield 56%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis of the obtained product, C- CH ₃ at 1.4 ppm (s, 9H) and Pyrene- H at 8.0-8.2 ppm (m, 9H) were confirmed.

Example 10: Synthesis of 2- sec -butylpyrene

In the same manner as in Example 1, 50 g (0.247 mol) of pyrene, 22.7 g (0.124 mol) of 2-iodobutane, 3.6 g (0.0124 mol) of tetrabutylphosphonium chloride and 50 ml of THF were added and reacted at 230°C for 6 hours. 16.3 g (0.06 mol, yield 51%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C-CH ₃ at 0.8 ppm (t,3H), C-Ch _{3 at 1.2 ppm (d, 3H), C-Ch 2 at} 1.5 ppm (m, 2H) - C, Pyrene-Ch-C at 2.6 ppm (m, 1H) and Pyrene-H at 8.0-8.2 ppm (m, 9H) were identified.

Example 11: Synthesis of 4-hexylbiphenyl

In the same manner as in Example 1, 50 g (0.324 mol) of biphenyl, 19.6 g (0.162 mol) of 1-chlorohexane, 4.8 g (0.0162 mol) of tetrabutylphosphonium chloride and 50 ml of THF were added and reacted at 230 ° C. for 6 hours. 23.2 g (0.10 mol, yield 60%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C-Ch _{2 at 0.88 ppm (t, 3H), C-Ch 2 -C} at 1.30 ppm (m, 6H), and Ph-C at 1.58 ppm (m, 2H). -Ch _{2 ,} Ph-Ch at 2.63 ppm ( _t , 2H) _, and Ph-h at 7.28-7.75 ppm (m, 9H) were confirmed.

Example 12: Synthesis of 9-(2-hexyl)anthracene

In the same manner as in Example 1, 50 g (0.28 mol) of anthracene, 16.9 g (0.14 mol) of 2-chlorohexane, 4.1 g (0.014 mol) of tetrabutylphosphonium chloride, and 50 ml of THF were added, and reacted at 230° C. for 6 hours to produce a product 18.4 g (0.07 mol, yield 49%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH 3 at 0.9 ppm (t, 3H), C- CH ₂ -C and C- CH ₃ at 1.3 ppm (m, 7H) _, 1.56 ppm (m, 2H) ) in Anth-C- CH ₂ , Anth-CH at 2.55 ppm (m, 1H), and Anth- H at 7.47-8.24 ppm (m, 9H) were confirmed.

Example 13: Synthesis of 2-isopropylpyrene

In the same manner as in Example 1, 30 g (0.15 mol) of pyrene, 6.3 g (0.08 mol) of isopropyl chloride, 3 g (0.01 mol) of tetrabutylphosphonium chloride and 50 ml of THF were added and reacted at 230 ° C. for 6 hours to 12.2 g of product (0.05 mol, 59%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH ₃ at 1.3ppm (d, 6H), Pyrene- CH at 2.9ppm (m, 1H), and Pyrene- H at 7.9-8.2ppm (m, 9H). Confirmed.

Example 14: Synthesis of 1-methyl-4-(2-pentyl)benzene

50 g (0.54 mol) of toluene and 40.9 g (0.27 mol) of 2-bromopentane and 3.7 g (0.027 of dimethylphenylphosphine) corresponding to 10% moles of 2-bromopentane in a 290 ml stainless steel tube. mol) and reacted at 230°C for 6 hours. This solution was taken out in a round-bottom flask, and 20.6 g (0.13 mol, yield 47%) of the product was obtained through distillation under reduced pressure. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C-CH _{3 at 0.89 ppm (t, 3H), Ph-C-CH 3} at _1.16 ppm (d, 3H), C - CH at 1.31 ppm (m, 2H) ₂ -C, Ph-C- CH at 1.54 ppm (m, 2H), Ph- CH ₃ at 2.19 ppm (s, _3H ), Ph- CH at 2.55 ppm (m, 1H), 7.06-7.11 ppm (m) , 4H) to confirm Ph- H .

Example 15: Synthesis of 1- sec -butyl-4-methylbenzene

In the same manner as in Example 14, 50 g (0.54 mol) of toluene, 49.9 g (0.27 mol) of 2-iodobutane, 3.2 g (0.027 mol) of triethylphosphine, and 50 ml of THF were added and reacted at 230° C. for 6 hours to produce a product 21.6 g (0.15 mol, yield 54%) was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was C- CH 3 at 0.73 ppm (t, 3H), Ph-C-CH ₃ at _1.16 ppm (d, 3H), Ph-C at 1.52 ppm (m, 2H) -CH ₂ , Ph- CH ₂ at 2.19ppm (s, 3H), Ph- CH at 2.55ppm (m, 1H), and Ph- H at 7.00ppm (m, 4H) were confirmed.

Example 16: Synthesis of 9,10-(bis(t-butyl))anthracene

30 g (0.17 mol) of anthracene, 70 g (0.51 mol) of t-butyl bromide, 8.9 g (0.03 mol) of tetrabutylphosphonium chloride and 50 ml of THF were placed in a high-temperature, high-pressure reactor made of 290 ml stainless steel tube at 230°C for 6 hours. reacted. This solution was taken out in a round bottom flask, and 29.6 g (0.1 mol, 62%) of the product was obtained through distillation under reduced pressure. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis of the obtained product, C- CH ₃ at 1.5 ppm (s, 18H) and Anth- H at 7.5-8.2 ppm (m, 8H) were confirmed.

Example 17: Synthesis of (9-(trichlorosilyl)methyl)anthracene

50 g (0.28 mol) of anthracene, 25.7 g (0.14 mol) of (chloromethyl) trichlorosilane, 1.9 g (0.014 mol) of dimethylphenylphosphine, and 50 ml of decane were placed in a high-temperature, high-pressure reactor made of 290 ml stainless steel tube under nitrogen atmosphere. The reaction was carried out at 230°C for 6 hours. The solution was taken out in a round bottom flask, washed 5 times with dried decane and filtered. The filtrate was distilled under reduced pressure to obtain 20.5 g (0.06 mol, yield 45%) of the product. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis of the obtained product, Anth- CH ₂ at 3.05 ppm (s, 2H) and Anth- H at 7.47-8.20 ppm (m, 9H) were confirmed.

Example 18: Synthesis of 5-(2-(trichlorosilyl)ethyl)tetracene

In the same manner as in Example 17, 50 g (0.219 mol) of tetracene, 21.7 g (0.11 mol) of 2-chloroethyltrichlorosilane, 3.2 g (0.011 mol) of tetrabutylphosphonium chloride, and 50 ml of decane were added, and 230°C for 6 hours. During the reaction, 21.9 g (0.06 mol, yield 51%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH ₂ -C at 1.7 ppm (t, 2H) and Tetracene- CH ₂ -C at 3.3 ppm (t, 2H) _, Tetracene- H was identified at 7.5-8.5 ppm (m, 11H).

Example 19: Synthesis of 3-(2-(trimethoxysilyl)ethyl)perylene

In the same manner as in Example 17, 50 g (0.198 mol) of perylene, 18.3 g (0.099 mol) of 2-chloroethyltrimethoxysilane, 2.9 g (0.0099 mol) of tetrabutylphosphonium chloride, and 50 ml of decane were added at 230 ° C. After reacting for an hour, 19.6 g (0.049 mol, yield 49%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH ₂ -C at 0.93 ppm (t, 2H), C- CH ₂ -C at 3.0 ppm (t, 2H), and Si at 3.6 ppm (s, 9H). - Perylene -H was confirmed in OCH ₃ , 7.2-8.2 ppm (m, 11H).

Example 20: Synthesis of 5-(trichloromethyl)tetracene

In the same manner as in Example 17, 50 g (0.219 mol) of tetracene, 20.1 g (0.11 mol) of (chloromethyl) trichlorosilane, 1.3 g (0.011 mol) of triethylphosphine and 50 ml of decane were added, and at 230° C. for 6 hours. The reaction gave 20.7 g (0.06 mol, yield 62%) of the product. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis of the obtained product, Tetracene- CH ₂ at 3.05 ppm (s, 2H) and Tetracene- H at 3.05 ppm (m, 11H) were confirmed.

Example 21: Synthesis of (4-phenoxybenzyl)trimethoxysilane

50 g (0.294 mol) of biphenyl ether and 25.1 g (0.147 mol) of (chloromethyl) trimethoxysilane, 4.1 g (0.0147 mol) of tricyclohexylphosphine and 50ml of hexane was added and reacted at 230°C for 6 hours. The solution was taken out in a round bottom flask, washed 5 times with dried hexane and filtered. The filtrate was distilled under reduced pressure to obtain 20.1 g (0.07 mol, yield 45%) of the product. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, Si- CH ₂ at 1.84 ppm (s, 2H), O- CH ₃ at 3.55 ppm (s, 9H), Ph- H at 7.06-7.42 ppm (m, 9H) was confirmed.

Example 22: Synthesis of 6-(trimethoxysilylmethyl)pentacene

In the same manner as in Example 21, 50 g (0.18 mol) of pentacene, 15.3 g (0.09 mol) of (chloromethyl) trimethoxysilane, 1.8 g (0.009 mol) of tributylphosphine, and 50 ml of hexane were added in the same manner as in Example 21, and at 230° C. for 6 hours. During the reaction, 19.7 g (0.05 mol, yield 53%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Pentacen- CH ₂ at 2.3 ppm (s, 2H), Si-O CH ₃ at 3.6 ppm (s, 9H), and Pentacen- at 7.5-8.3 ppm (m, 13H). H was confirmed.

Example 23: Synthesis of 9-(2-(trichlorosilyl)ethyl)-10-methylanthracene

In the same manner as in Example 21, 50 g (0.26 mol) of 9-methylanthracene, 25.7 g (0.13 mol) of 2-chloroethyltrichlorosilane, 2.6 g (0.013 mol) of tributylphosphine, and 50 ml of hexane were added at 230 ° C. After reacting for an hour, 25.8 g (0.07 mol, yield 56%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH ₂ at 1.7 ppm (t, 2H), Anth- CH ₃ at 2.7 ppm (t, 3H), and Si-C- CH at 3.3 ppm (t, 2H). ₂ , Anth- H was confirmed at 7.5-8.2 ppm (m, 8H).

Example 24: Synthesis of 1-(2-(trimethoxysilyl)ethyl)naphthalene

In the same manner as in Example 21, 50 g (0.39 mol) of naphthalene, 36 g (0.195 mol) of 2-chloroethyltrimethoxysilane, 5.8 g (0.0195 mol) of tetrabutylphosphonium chloride, and 50 ml of hexane were added, and at 230° C. for 6 hours. The product was reacted to obtain 24.3 g (0.09 mol, yield 45%) of the product. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH ₂ at 0.9 ppm (t, 2H), Si-C- CH ₂ at 2.9 ppm (t, 2H), and Si-O at 3.6 ppm (s, 9H). CH ₃ , Naph- H was identified in 6.9-8.1 ppm (m, 7H).

Example 25: Synthesis of 9-((trimethoxysilyl)methyl)anthracene

In the same manner as in Example 21, 50 g (0.28 mol) of anthracene, 23.9 g (0.14 mol) of (chloromethyl) trimethoxysilane, 4.1 g (0.014 mol) of tetrabutylphosphonium chloride and 50 ml of decane were added, and then at 230° C. for 6 hours. During the reaction, 21 g (0.07 mol, yield 48%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH ₂ at 2.28 ppm (s, 2H), Si-O CH ₃ at 3.55 ppm (s, 9H), Anth- at 7.47-8.28 ppm (m, 9H) H was confirmed.

Example 26: Synthesis of 6-(2-(trichlorosilyl)ethyl)pentacene

In the same manner as in Example 21, 50 g (0.18 mol) of pentacene, 17.8 g (0.09 mol) of 2-chloroethyltrichlorosilane, 2.7 g (0.009 mol) of tetrabutylphosphonium chloride, and 50 ml of decane were added, and 230 ° C. for 6 hours. During the reaction, 20.6 g (0.05 mol, yield 52%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH 2 at 1.70 ppm (t, 2H), Si-C-CH ₂ at _3.30 ppm (t, 2H), and Pentacen at 7.54-8.25 ppm (m, 13H). - H was confirmed.

Example 27: Synthesis of 4-((trichlorosilyl)methyl)toluene

50 g (0.543 mol) of toluene, 49.9 g (0.27 mol) of (chloromethyl) trichlorosilane and 8 g (0.027 mol) of tetrabutylphosphonium chloride were placed in a high-temperature, high-pressure reactor made of 290 ml stainless steel tube under nitrogen atmosphere, and at 230 ° C. The reaction was carried out for 6 hours. The solution was taken out in a round bottom flask, washed 5 times with dried hexane and filtered. The filtrate was distilled under reduced pressure to obtain 38.8 g (0.16 mol, yield 60%) of the product. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Ph- CH ₃ at 2.19ppm (s, 3H), Si- CH ₂ at 2.61ppm (s, 2H), Ph- H at 7.01-7.11ppm (m, 4H) was confirmed.

Example 28: Synthesis of 1,5-bis((trichlorosilyl)methyl)naphthalene

30g (0.23mol) of naphthalene and 126.9g (0.69mol) of chloromethyltrichlorosilane, tetrabutylphosphonium chloride corresponding to 5% moles of chloromethyltrichlorosilane in a high-temperature, high-pressure reactor made of 290ml stainless steel tube under nitrogen atmosphere 11.8 g (0.04 mol) and 40 ml of hexane were added and reacted at 230° C. for 6 hours. The solution was taken out in a round bottom flask, washed 5 times with dried hexane and filtered. The filtrate was distilled under reduced pressure to obtain 59.2 g (0.14 mol, yield 63%) of the product. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis of the obtained product, Si- CH ₂ at 3.1 ppm (s, 4H) and Naph- H at 6.9-7.8 ppm (m, 6H) were confirmed.

Example 29: Synthesis of 9,10-bis((trimethoxysilyl)methyl)anthracene

In the same manner as in Example 28, 20 g (0.11 mol) of anthracene, 58 g (0.34 mol) of chloromethyltrimethoxysilane, 5.9 g (0.02 mol) of tetrabutylphosphonium chloride and 50 ml of hexane were added and reacted at 230 ° C. for 6 hours. 26.8 g (0.06 mol, yield 57%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH ₂ at 2.3 ppm (s, 4H), Si- OCH ₃ at 3.6 ppm (s, 9H), and Anth- H at 7.5-8.2 ppm (m, 8H). was confirmed.

Example 30: Synthesis of 9,10-bis((2-dichloromethylsilyl)ethyl)anthracene

In the same manner as in Example 28, 20 g (0.11 mol) of anthracene, 58.6 g (0.33 mol) of 2-chloroethylmethyldichlorosilane, 5.9 g (0.02 mol) of tetrabutylphosphonium chloride and 50 ml of hexane were added, and then at 230°C for 6 hours. During the reaction, 29.9 g (0.06 mol, yield 59%) of the product was obtained. As a result of 300 MHz hydrogen nuclear magnetic resonance analysis, the obtained product was Si- CH ₃ at 0.7 ppm (s, 6H), Si- CH ₂ at 0.9 ppm (t, 4H), Anth- CH ₂ at 2.9 ppm (t, 4H), Anth- H was confirmed at 7.5-8.2 ppm (m, 8H).

Claims (11)

to the alkylarene compound represented by the formula (3)
Formula 3:

wherein R ¹ = an alkyl group having 1 to 10 carbon atoms or (CH ₂ ) _q Si(R ³ ) _p (OR ⁴ ) _3-p (q=1-10, R ³ = Cl or CH ₃ , p=0, 1, 2, 3, R ⁴ =CH ₃ or C ₂ H ₅ ); n = 0, 1, 2 or 3; Ar = benzene, naphthalene, anthracene, biphenyl, terphenylene, anthrone, anthraquinone, pyrene, phenanthrene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, anisole, thioani sol, tetracene, pentacene and aromatic compounds having 1 to 8 rings; R ² = an alkyl group having 1 to 8 carbon atoms or an alkyl group including a phenyl group; l = 0, 1, 2, 3 or 4; And m = 1, 2 or 3, characterized in that the alkylarene compound. The method according to claim 1, wherein Ar = anthracene, biphenyl, terphenylene, anthrone, anthraquinone, pyrene, phenantrancene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, anisole, thio anisole, tetracene or pentacene;

= methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, sec-butyl, trimethylsilylmethyl, trichlorosilylmethyl, trimethoxysilylmethyl, triethoxysilylmethyl, methyl Dichlorosilylmethyl, methyldimethoxysilylmethyl, dimethylchlorosilylmethyl, dimethylmethoxysilylmethyl, dimethylethoxysilylmethyl, trichlorosilylethyl, trimethoxysilylethyl, triethoxysilylethyl, tri chlorosilylpropyl, trimethoxysilylpropyl, triethoxysilylpropyl, trichlorosilylhexyl, trimethoxysilylhexyl, triethoxysilylhexyl; R ² =CH ₃ or C ₂ H ₅ ; m=1,2 or 3; And l = 0, 1 or 2, characterized in that the alkylarene compound. A method for producing an alkali arene compound represented by Formula 3, which is produced by reacting the compound represented by Formula 1 and Formula 2 with an organophosphine compound as a catalyst.
Formula 1:

Formula 2:

Formula 3:

In Formulas 1, 2 and 3, R ¹ = an alkyl group having 1 to 10 carbon atoms or (CH ₂ ) _q Si(R ³ ) _p (OR ⁴ ) _3-p (q=1-10, R ³ = Cl or CH ₃ , p=0, 1, 2, 3, R ⁴ =CH ₃ or C ₂ H ₅ ); n=0, 1, 2 or 3; X=Cl, Br or I; Ar = benzene, naphthalene, anthracene, biphenyl, terphenylene, anthrone, anthraquinone, pyrene, phenanthrene, perylene, biphenyl ether, biphenyl sulfide, anisole, fluorene, anisole, thioani sol, tetracene, pentacene and aromatic compounds having 1 to 8 rings; R ² = H, an alkyl group having 1 to 8 carbon atoms or an alkyl group including a phenyl group; l = 0, 1, 2, 3 or 4; And m = 1, 2 or 3, characterized in that the production method of the alkylarene compound. The method according to claim 3, wherein the reaction molar ratio of the compound represented by Formula 1 to the compound represented by Formula 2 is 6:1 to 1:3. The method according to claim 3, wherein the compound represented by Formula 4 is used as a catalyst,
Formula 4:
P(R") ₃ ,
In the above, R" is an alkyl group having 1 to 12 carbon atoms or a phenyl group that is alkenyl, and different R" is a method for producing an alkylarene compound, characterized in that it has a cyclic structure connected by a covalent bond. The method according to claim 3, wherein the compound represented by Formula 5 is used as a catalyst,
Formula 5:
P(R") ₄ X'
In the above, R" includes a phenyl group that is an alkyl group or alkenyl group having 1 to 12 carbon atoms, different R" is a cyclic structure connected by a covalent bond, and X'=Cl, Br, or I is one selected from A method for producing an alkyl arene characterized in that. The method according to claim 3, wherein the compound represented by Formula 6 is used as a catalyst,
Formula 6:
X'(R") ₃ PYP(R") ₃ X
In the above, R″ includes a phenyl group having 1 to 12 carbon atoms or an alkenyl group, and different R″ are cyclic structures connected by a covalent bond, X′=Cl, Br or I, and Y=C1 A method for producing an alkyl arene, characterized in that it is an alkyl group of 12, an alkyl group including an aromatic group, or an aromatic group. 7. The method according to any one of claims 3 to 6,
The catalyst concentration is 5 to 20 mol% based on the compound of formula (1) A method for producing an alkylarene, characterized in that. The method according to claim 3, wherein the reaction temperature is 100 ~ 250 ℃ method for producing an alkylarene compound, characterized in that The method according to claim 3, wherein the reaction solvent is at least one selected from the group consisting of hydrocarbon, ether, dimethoxyethane (DME) and THF. The method according to claim 3, wherein when the compound of Formula 1 and the compound of Formula 2 are liquid, they are reacted without a solvent.