Novel alkoxyaminosilylamine compound, preparation method therefor, silicon-containing thin film deposition composition comprising same, and method for manufacturing silicon-containing thin film by using same

Abstract

The present invention relates to a novel alkoxyaminosilylamine compound, a preparation method therefor, a silicon-containing thin film deposition composition comprising same, and a method for manufacturing a silicon-containing thin film by using same. The alkoxyaminosilylamine compound according to the present invention is thermally stable and has high volatility and reactivity, and thus is very useful for stably manufacturing a silicon-containing thin film having excellent properties in a wide temperature range.

Description

A novel alkoxyaminosilylamine compound, a method for preparing the same, a composition for depositing a silicon-containing thin film comprising the same, and a method for preparing a silicon-containing thin film using the same

[0001] The present invention relates to a novel alkoxyaminosilylamine compound, a method for preparing the same, a composition for depositing a silicon-containing thin film comprising the same, and a method for preparing a silicon-containing thin film using the same.

[0002] Silicon-containing thin films are manufactured into various types of thin films, such as silicon films, silicon oxide films, silicon nitride films, silicon carbonitride films, and silicon oxynitride films, through various deposition processes in the semiconductor field. Recently, polycrystalline silicon thin films are being used in thin film transistors (TFTs), solar cells, etc., and their application fields are becoming increasingly diverse.

[0003] Representative technologies known for manufacturing thin films containing silicon include MOCVD, in which a mixed gaseous silicon precursor and a reactant gas react to form a film on the surface of a substrate or react directly on the surface to form a film; and atomic layer deposition (ALD), in which a gaseous silicon precursor is physically or chemically adsorbed onto the surface of a substrate and then a film is formed by sequentially introducing reactant gases. Various thin film manufacturing technologies, such as low-pressure chemical vapor deposition (LPCVD) that applies this, plasma-enhanced chemical vapor deposition (PECVD) that enables deposition at low temperatures, and atomic layer deposition (PEALD), are being applied to the manufacturing processes of next-generation semiconductor and display devices to form ultra-fine patterns and deposit ultra-thin films that have uniform and excellent properties at a thickness of the nanometer scale.

[0004] Precursors used for forming silicon-containing thin films are typically compounds in the form of silane, silane chloride, amino silane, and alkoxy silane. Specific examples include silane chloride compounds such as dichlorosilane (SiH2Cl2) and hexachlorodisilane (Cl3SiSiCl3), trisilylamine (N(SiH3)3), bis-diethylaminosilane (H2Si(N(CH2CH3)2)2), and diisopropylaminosilane (H3SiN(i-C3H7)2), which are used in the mass production process of semiconductor manufacturing and display manufacturing.

[0005] However, due to the miniaturization of devices and the increase in aspect ratio and the diversification of device materials caused by the ultra-high integration of devices, a technology for forming ultra-fine thin films with excellent electrical properties and a uniformly thin thickness at a desired low temperature is required. Therefore, the high-temperature process of over 600℃ using existing silicon precursors, step coverage and etching characteristics, and the physical and electrical properties of the thin films are becoming issues, and the development of a novel, superior silicon precursor is required.

[0006] The purpose of the present invention is to provide a novel alkoxyaminosilylamine compound and a method for producing the same.

[0007] Specifically, one object of the present invention is to provide a thermally stable and highly volatile alkoxyaminosilylamine compound useful as a precursor for forming a silicon-containing thin film.

[0008] Specifically, one object of the present invention is to provide a novel alkoxyaminosilylamine compound, which is a precursor compound capable of forming a stable silicon-containing thin film with excellent reactivity over a wide temperature range.

[0009] In addition, the present invention provides a composition for silicon-containing thin film deposition comprising an alkoxyaminosilylamine compound according to one embodiment of the present invention.

[0010] In addition, the present invention provides a method for forming a silicon-containing thin film having excellent properties using the alkoxyaminosilylamine compound or a composition for depositing a silicon-containing thin film containing the same.

[0011] The present invention provides an alkoxyaminosilylamine compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R 1 Inland R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen;

[0016] R 5 Inland R 8 are independently C1-C10 alkyl.

[0017] According to one embodiment, a compound is, in the chemical formula 1, R 1 Inland R 4 are independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl or halogen; R 5 Inland R 8 can be independently C1-C5 alkyl.

[0018] According to one embodiment, a compound is, in the chemical formula 1, R 1 Inland R 4 are independently hydrogen or C1-C5 alkyl; R 5 Inland R 8 can be independently C1-C5 alkyl.

[0019] According to one embodiment, a compound is, in the chemical formula 1, R 1 Inland R 4are independently hydrogen, C1-C3 alkyl, C2-C4 alkenyl or halogen; R 5 Inland R 8 can be independently C1-C3 alkyl.

[0020] According to one embodiment, a compound is, in the chemical formula 1, R 1 Inland R 4 are independently hydrogen or C1-C3 alkyl; R 5 Inland R 8 can be independently C1-C3 alkyl.

[0021] According to one embodiment, the chemical formula 1 may be at least one selected from the following structures.

[0022]

[0023]

[0024]

[0025] In addition, the present invention provides a method for producing an alkoxyaminosilylamine compound, including the step of producing an alkoxyaminosilylamine compound of the following chemical formula 1 by reacting a compound of the following chemical formula 3 and a compound of the following chemical formula 4 under a C1-C5 alkyllithium.

[0026] [Chemical Formula 1]

[0027]

[0028] [Chemical Formula 3]

[0029]

[0030] [Chemical Formula 4]

[0031]

[0032] In the above chemical formulas 1, 3 and 4,

[0033] R 1 Inland R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen;

[0034] R5 Inland R 8 are independently C1-C10 alkyl;

[0035] X is a halogen.

[0036] A method for producing an alkoxyaminosilylamine compound according to one embodiment may include a step of reacting a compound of the following chemical formula 4 with a compound of the following chemical formula 5 in the presence of a C1-C5 alkyl lithium to produce a compound of the following chemical formula 6; and a step of adding a reducing agent to the following chemical formula 6 to produce an alkoxyaminosilylamine compound of the following chemical formula 1-1.

[0037] [Chemical Formula 1-1]

[0038]

[0039] [Chemical Formula 4]

[0040]

[0041] [Chemical Formula 5]

[0042]

[0043] [Chemical Formula 6]

[0044]

[0045] In the above chemical formulas 1-1, 4, 5 and 6,

[0046] R 1 , R 3 and R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen;

[0047] R 5 Inland R 8 are independently C1-C10 alkyl;

[0048] X is a halogen.

[0049] In addition, the present invention provides a composition for silicon-containing thin film deposition comprising an alkoxyaminosilylamine compound represented by the following chemical formula 2.

[0050] [Chemical Formula 2]

[0051]

[0052] In the above chemical formula 2,

[0053] R 9 Inland R 13 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen;

[0054] R 14 Inland R 17 are independently C1-C10 alkyl.

[0055] According to one embodiment, a composition for thin film deposition containing silicon is, in the chemical formula 2, R 9 Inland R 13 are independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl or halogen; R 14 Inland R 17 can be independently C1-C5 alkyl.

[0056] According to one embodiment, the chemical formula 2 may be at least one selected from the following structures.

[0057]

[0058]

[0059]

[0060]

[0061] In addition, the present invention provides a method for producing a silicon-containing thin film by producing a thin film using an alkoxyaminosilylamine compound according to one embodiment.

[0062] In addition, the present invention provides a method for manufacturing a silicon-containing thin film, which manufactures a thin film using a composition for silicon-containing thin film deposition according to one embodiment.

[0063] The alkoxyaminosilylamine compound according to the present invention can be provided as a precursor of a thermally stable and highly volatile silicon-containing thin film, thereby forming a silicon-containing thin film with excellent properties.

[0064] In addition, the alkoxyaminosilylamine compound according to the present invention can have excellent reactivity in a wide temperature range when manufacturing a silicon-containing thin film using the same.

[0065] In addition, a silicon-containing thin film deposition composition according to one embodiment of the present invention can produce a high-quality silicon-containing thin film by including an alkoxyaminosilylamine compound according to one embodiment of the present invention.

[0066] In addition, the method for producing an alkoxyaminosilylamine compound according to one embodiment of the present invention can produce a high-purity alkoxyaminosilylamine compound in a high yield.

[0067] Figure 1 is a thermogravimetric (TGA) graph of the alkoxyaminosilylamine compounds prepared in Examples 1 and 2.

[0068] Figure 2 is a differential scanning calorimetry (DSC) graph of the alkoxyaminosilylamine compounds prepared in Examples 1 and 2.

[0069] Hereinafter, the present invention will be described in more detail. Unless otherwise defined, the technical and scientific terms used herein have the meanings commonly understood by those of ordinary skill in the art to which this invention pertains. In the following description, descriptions of well-known functions and configurations that may unnecessarily obscure the gist of the present invention will be omitted.

[0070] The term "CA-CB" in this specification means "having carbon atoms of A or more and B or less", and the term "A to B" means "having carbon atoms of A or more and B or less".

[0071] The term “alkyl” as used herein refers to a monovalent substituent, including both linear and branched forms.

[0072] The above alkyl may have 1 to 10 carbon atoms, specifically 1 to 5 carbon atoms, and more specifically 1 to 3 carbon atoms.

[0073] The above alkyl includes, but is not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, hexyl, and the like, for example.

[0074] The term “alkoxy” as used herein refers to an -O-alkyl radical, where “alkyl” is as defined above. Specific examples include, but are not limited to, methoxy, ethoxy, isopropoxy, butoxy, isobutoxy, t-butoxy, and the like.

[0075] The term “alkenyl” as used herein means a linear or branched hydrocarbon having at least one carbon-carbon double bond.

[0076] The above alkenyl may have 2 to 10 carbon atoms, specifically 2 to 7 carbon atoms, and more specifically 2 to 5 carbon atoms.

[0077] Examples of the above alkenyl include, but are not limited to, vinyl, allyl, butenyl, isobutenyl, pentenyl, hexenyl, and the like.

[0078] The term “halogen” as used herein means an element of Group 17 and may be any one selected from F, Cl, Br, and I.

[0079] Additionally, the term “includes” in this specification is an open-ended description having an equivalent meaning to expressions such as “comprises,” “contains,” “has,” or “characterizes,” and does not exclude additional elements, materials, or processes not listed.

[0080] Additionally, the singular forms used herein may be intended to include the plural forms as well, unless the context specifically indicates otherwise.

[0081] The term “thermal stability” in this specification may mean that the physical properties do not change even during a continuous heating process or a high temperature process, and specifically means that the structural changes do not occur even when exposed for a long period of time under the harsh conditions described above.

[0082] The term “silicon-containing thin film with excellent properties” as used herein means a high-quality silicon-containing thin film with high silicon content and excellent thermal stability and durability.

[0083] In this specification, “normal temperature” may mean a temperature without artificial temperature control, and for example, the normal temperature may be 20°C to 40°C, 20°C to 30°C, or 23°C to 26°C.

[0084] The present invention provides a novel alkoxyaminosilylamine compound useful as a precursor for producing a silicon-containing thin film, and the alkoxyaminosilylamine compound of the present invention is represented by the following chemical formula 1.

[0085] [Chemical Formula 1]

[0086]

[0087] In the above chemical formula 1,

[0088] R 1 Inland R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen;

[0089] R 5 Inland R 8 are independently C1-C10 alkyl.

[0090] The alkoxyaminosilylamine compound of the present invention has a structure in which an alkoxy functional group is introduced to a silicon atom of a trisilylamine structure, and due to the alkoxy functional group introduced to the silicon atom, it has lower activation energy, thereby improving reactivity, and does not generate nonvolatile byproducts, so that a high-purity silicon-containing thin film can be easily formed at a high deposition rate.

[0091] In an alkoxyaminosilylamine compound according to one embodiment, R in the chemical formula 1 1 Inland R 4 are independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl or halogen; R 5 Inland R 8 can be independently C1-C5 alkyl.

[0092] In an alkoxyaminosilylamine compound according to one embodiment, R in the chemical formula 1 1 Inland R 4 are independently hydrogen or C1-C5 alkyl; R 5 Inland R 8 can be independently C1-C5 alkyl.

[0093] In an alkoxyaminosilylamine compound according to one embodiment, in the chemical formula 1, R 1 Inland R 4 are independently hydrogen, C1-C3 alkyl, C2-C4 alkenyl or halogen; R 5 Inland R 8 can be independently C1-C3 alkyl.

[0094] In an alkoxyaminosilylamine compound according to one embodiment, R in the chemical formula 1 1 Inland R 4 are independently hydrogen or C1-C3 alkyl; R 5 Inland R 8 can be independently C1-C3 alkyl.

[0095] According to one specific example, the chemical formula 1 may be selected from the following compounds, but is not limited thereto.

[0096]

[0097]

[0098]

[0099] In addition, the present invention provides a method for producing the alkoxyaminosilylamine compound.

[0100] As one embodiment, a method for producing an alkoxyaminosilylamine compound is provided, including the step of producing an alkoxyaminosilylamine compound of the following formula 1 by reacting a compound of the following formula 3 and a compound of the following formula 4 under a C1-C5 alkyllithium.

[0101] [Chemical Formula 1]

[0102]

[0103] [Chemical Formula 3]

[0104]

[0105] [Chemical Formula 4]

[0106]

[0107] In the above chemical formulas 1, 3 and 4,

[0108] R 1 Inland R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen;

[0109] R 5 Inland R 8 are independently C1-C10 alkyl;

[0110] X is a halogen.

[0111] In the above manufacturing method, alkyllithium is a compound in which lithium is bonded to C1-C5 alkyl, and specifically may be methyllithium, ethyllithium, n-butyllithium, and preferably n-butyllithium.

[0112] In the above manufacturing method, the halogen may be any one halogen selected from F, Cl, Br and I, and preferably, the X may be Cl.

[0113] A method for producing an alkoxyaminosilylamine compound according to one embodiment may include a step of reacting a compound of the following chemical formula 4 with a compound of the following chemical formula 5 in the presence of a C1-C5 alkyl lithium to produce a compound of the following chemical formula 6; and a step of adding a reducing agent to the following chemical formula 6 to produce an alkoxyaminosilylamine compound of the following chemical formula 1-1.

[0114] [Chemical Formula 1-1]

[0115]

[0116] [Chemical Formula 4]

[0117]

[0118] [Chemical Formula 5]

[0119]

[0120] [Chemical Formula 6]

[0121]

[0122] In the above chemical formulas 1-1, 4, 5 and 6,

[0123] R 1 , R 3 and R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen;

[0124] R 5 Inland R 8 are independently C1-C10 alkyl;

[0125] X is a halogen.

[0126] In the above manufacturing method, alkyllithium is a compound in which lithium is bonded to C1-C5 alkyl, and specifically may be methyllithium, ethyllithium, n-butyllithium, and preferably n-butyllithium.

[0127] In the above manufacturing method, the halogen may be any one halogen selected from F, Cl, Br and I, and preferably, the X may be Cl.

[0128] In the above manufacturing method, the reducing agent may preferably be a compound capable of introducing hydrogen into the product through a reaction. Specifically, it may be a metal hydride capable of providing hydrogen, and for example, it may be at least one selected from CaH2, LiAlH4, LiBH4, NaBH4, NaH, LiH, and KH. More preferably, the reducing agent may be LiAlH4 or LiH, but is not limited thereto. The reducing agent is preferable because, when added to the above chemical formula 6, it can replace the halogen atom of the chemical formula 6 with hydrogen.

[0129] According to one embodiment, all of the above reactions can be performed in an organic solvent, and specifically, one or more mixed organic solvents selected from hexane, diethyl ether, toluene, tetrahydrofuran, etc. can be used, but are not limited thereto.

[0130] In addition, in all of the above reactions, the reaction temperature can be used at a temperature used in conventional organic synthesis, but the reaction time may vary depending on the amount of reactants and starting materials.

[0131] After the above reaction, the purity can be increased by removing by-products through filtration, extraction, recrystallization, distillation, sublimation, chromatography, etc.

[0132] The alkoxyaminosilylamine compound manufactured by the above method is not only thermally stable and highly volatile, so that it can be used to form a silicon-containing thin film with excellent properties, but also has excellent reactivity over a wide temperature range, so that a silicon-containing thin film can be manufactured stably.

[0133] In addition, according to the method for producing the above alkoxyaminosilylamine compound, a high-purity alkoxyaminosilylamine compound can be produced in a high yield.

[0134] In addition, the present invention provides a composition for silicon-containing thin film deposition, comprising a compound represented by the following chemical formula 2.

[0135] [Chemical Formula 2]

[0136]

[0137] In the above chemical formula 2, R 9 Inland R 13 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen; R 14 Inland R 17 are independently C1-C10 alkyl.

[0138] According to one embodiment, a composition for thin film deposition containing silicon is, in the chemical formula 2, R 9 Inland R 13 are independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl or halogen; R 14 Inland R 17 can be independently C1-C5 alkyl.

[0139] According to one embodiment, a composition for thin film deposition containing silicon is, in the chemical formula 2, R 9 Inland R 13 are independently hydrogen, C1-C3 alkyl, C2-C3 alkenyl or halogen; R 14 Inland R 17 can be independently C1-C3 alkyl.

[0140] The alkoxyaminosilylamine compound included in the silicon-containing thin film deposition composition of the present invention has a structure in which an alkoxy functional group is introduced to a silicon atom of a trisilylamine structure, and due to the alkoxy functional group introduced to the silicon atom, it has lower activation energy, thereby improving reactivity, and does not generate nonvolatile byproducts, so that a high-purity silicon-containing thin film can be easily formed at a high deposition rate.

[0141] In addition, since the composition for depositing a silicon-containing thin film has a high content of silicon atoms in the molecule, it not only easily deposits a high-quality silicon-containing thin film at a high deposition rate, but also has excellent thermal stability, so that it can produce a thin film with high durability and excellent purity.

[0142] The composition for depositing a silicon-containing thin film of the present invention may be included within a content range that can be recognized by a person skilled in the art, taking into consideration the film formation conditions of the thin film or the thickness, characteristics, etc. of the thin film.

[0143] According to one specific example, the chemical formula 2 may be selected from the following structures, but is not limited thereto.

[0144]

[0145]

[0146]

[0147]

[0148] In addition, the present invention provides a method for producing a silicon-containing thin film by producing a thin film using the alkoxyaminosilylamine compound or the silicon-containing thin film deposition composition described above.

[0149] A method for manufacturing a silicon-containing thin film according to one embodiment can manufacture a silicon-containing thin film with excellent properties by manufacturing a thin film using a composition for depositing a silicon-containing thin film that includes the thermally stable and highly volatile alkoxyaminosilylamine compound as a precursor.

[0150] According to one embodiment, a method for manufacturing a silicon-containing thin film can be performed by any method within the scope recognizable by a person skilled in the art, and preferably, it can be performed by atomic layer deposition (ALD), chemical vapor deposition (CVD), metalorganic chemical vapor deposition (MOCVD), low pressure vapor deposition (LPCVD), plasma enhanced vapor deposition (PECVD), or plasma enhanced atomic layer deposition (PEALD). In terms of making thin film deposition easier and allowing the manufactured thin film to have excellent properties, plasma enhanced atomic layer deposition (PEALD) or plasma enhanced vapor deposition (PECVD) is preferred.

[0151] A method for manufacturing a silicon-containing thin film according to one embodiment may specifically include the steps of: a) heating and maintaining the temperature of a substrate mounted in a chamber at 30 to 400°C; b) contacting the substrate with a composition for depositing a silicon-containing thin film according to one embodiment and allowing it to be adsorbed; and c) depositing a silicon-containing thin film on the substrate by injecting a reaction gas.

[0152] Preferably, when performing the silicon-containing thin film according to one embodiment of the present invention by plasma-enhanced atomic layer deposition (PEALD) or plasma-enhanced vapor deposition (PECVD), a step of generating plasma may be further included after step a). In addition, in step b), the composition for depositing a silicon-containing thin film according to one embodiment may be injected together with a transport gas.

[0153] In a method for manufacturing a silicon-containing thin film according to one embodiment, deposition conditions can be controlled according to the structure or thermal characteristics of the desired thin film, and examples of the deposition conditions according to one specific example include an input flow rate of a silicon-containing thin film deposition composition containing an alkoxyaminosilylamine compound, an input flow rate of a reaction gas, a carrier gas, pressure, RF power, substrate temperature, etc., and non-limiting examples of such deposition conditions include an input flow rate of a silicon-containing thin film deposition composition of 10 to 1000 cc / min, a carrier gas of 10 to 1000 cc / min, a flow rate of a reaction gas of 1 to 1000 cc / min, a pressure of 0.5 to 10 torr, an RF power of 200 to 1000 W, and a substrate temperature of 30 to 400°C, preferably 100 to 350°C, but are not limited thereto.

[0154] According to one embodiment, the silicon-containing thin film may be any thin film that can be manufactured within a range recognizable by those skilled in the art, and specifically, may be a silicon oxide film (SiO2), a silicon oxycarbide film (SiOC), a silicon nitride film (SiN), a silicon oxynitride film (SiON), a silicon carbonitride film (SiCN), or a silicon carbide film (SiC), and in addition, various high-quality thin films containing silicon can be manufactured within a range recognizable by those skilled in the art.

[0155] In the method for manufacturing a silicon-containing thin film according to one embodiment, the reaction gas used may be any gas that is typically used with a silicon precursor, taking into consideration the material of the silicon-containing thin film to be manufactured. As a specific example, the reaction gas may be any one or two or more selected from oxygen (O2), ozone (O3), distilled water (H2O), hydrogen peroxide (H2O2), nitrogen monoxide (NO), nitrous oxide (N2O), nitrogen dioxide (NO2), ammonia (NH3), nitrogen (N2), hydrazine (N2H4), amines, diamines, carbon monoxide (CO), carbon dioxide (CO2), C1 to C12 saturated or unsaturated hydrocarbons, hydrogen, argon, and helium, and the transport gas may be one or two or more selected from argon, helium, and nitrogen, but is not limited thereto.

[0156] The substrate used in the method for manufacturing a silicon-containing thin film according to one specific example may be, but is not limited to, a substrate including one or more semiconductor materials selected from the group consisting of Si, Ge, SiGe, GaP, GaAs, SiC, SiGeC, InAs, and InP; a silicon-on-insulator (SOI) substrate; a quartz substrate; or a glass substrate for a display; a flexible plastic substrate such as polyimide, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polymethyl methacrylate (PMMA), polycarbonate (PC), polyethersulfone (PES), and polyester; etc.

[0157] In addition, in addition to forming the silicon-containing thin film directly on the substrate, a plurality of conductive layers, dielectric layers, or insulating layers may be formed between the substrate and the silicon-containing thin film.

[0158] Hereinafter, embodiments of the present invention will be described in detail. However, these are provided to enable those skilled in the art to easily implement the present invention. The present invention may be implemented in various different forms, and the spirit of the present invention is not necessarily limited to the embodiments.

[0159] The alkoxyaminosilylamine compound according to one embodiment of the present invention is 1 H NMR, 13 C NMR and 29 The structure was analyzed using Si-NMR spectra.

[0160] Additionally, the thermal stability, volatility, and decomposition temperature of the obtained alkoxyaminosilylamine compounds were measured through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC).

[0161] [Example 1] Synthesis of bis[dimethylmethoxysilyl](dimethylsilyl)amine

[0162]

[0163] Hexane (C6H) was placed in a flame-dried 2 L flask under an anhydrous and inert atmosphere. 14 ) 206g (2.39mol) and bis(methoxydimethylsilyl)amine ([(CH3)2(OCH3)Si]2NH) 71.3g (0.37mol) were added, and then n-butyllithium (2.68M, 137.8ml) was slowly added while maintaining the internal temperature at -20℃. After completing the addition, the reaction solution was gradually raised to room temperature and stirred at room temperature for 4 hours. In a 2L flask flame-dried under an anhydrous and inert atmosphere, hexane (C6H 14) 95.3 g (1.11 mol) and 34.9 g (0.37 mol) of chlorodimethylsilane ((CH3)2ClSiH) were added, and then 73.5 g (0.37 mol) of the produced bis(methoxydimethylsilyl)amine lithium salt ([(CH3)2(OCH3)Si]2NLi) was slowly added while maintaining the temperature at -20℃. After completion, the reaction solution was gradually raised to room temperature and stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was filtered to remove lithium chloride salt (LiCl), and the solvent was removed from the obtained filtrate under reduced pressure, followed by distillation under reduced pressure to obtain 53.7 g (0.21 mol) of the title compound, bis[methoxydimethylsilyl](dimethylsilyl)amine ([(CH3)2(OCH3)Si]2N-SiH(CH3)2). (Yield 57.9%)

[0164] 1 H-NMR (C6D6): δ 4.76(m, 1H (SiH(CH3)2), δ 3.25(s, 6H (CH3)2(OCH3)Si, δ 0.35(d, 6H (SiH(CH3)2), δ 0.25(s, 12H [(CH3)2(OCH3)Si]2N)

[0165] 29 Si-NMR (C6D6): δ-13.71 (SiH(CH3)2) δ1.34 ([(CH3)2(OCH3)Si]2N)

[0166] [Example 2] Synthesis of bis[dimethylmethoxysilyl](methylsilyl)amine

[0167]

[0168] Hexane (C6H) was placed in a flame-dried 2 L flask under an anhydrous and inert atmosphere. 14) 379.3g (4.40mol) and bis(methoxydimethylsilyl)amine ([(CH3)2(OCH3)Si]2NH) 170.3g (0.88mol) were added, and then n-butyllithium (2.60M, 339.5ml) was slowly added while maintaining the internal temperature at -20℃, and stirred at room temperature for 4 hours to prepare bis(methoxydimethylsilyl)amine lithium salt ([(CH3)2(OCH3)Si]2NLi) 175.5g (0.88mol).

[0169] Hexane (C6H) was placed in a flame-dried 3 L flask under an anhydrous and inert atmosphere. 14 ) 227.6g (2.64mol) and dichloromethylsilane ((CH3)Cl2SiH) 101.3g (0.88mol) were added, and then 175.5g (0.88mol) of bis(methoxydimethylsilyl)amine lithium salt ([(CH3)2(OCH3)Si]2NLi) prepared while maintaining the temperature at -20℃ was slowly added. After completion, the reaction solution was gradually heated to room temperature and stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was filtered to remove lithium chloride salt (LiCl), and the solvent was removed under reduced pressure from the obtained filtrate, followed by distillation under reduced pressure to obtain 213.0g (0.78mol) of bis[methoxydimethylsilyl](chloromethylsilyl)amine ([(CH3)2(OCH3)Si]2N-SiHCl(CH3)). (Yield 88.6%)

[0170] In a 1 L flame-dried flask under an anhydrous and inert atmosphere, 225.9 g (3.13 mol) of tetrahydrofuran (C4H8O) and 213.0 g (0.78 mol) of bis[methoxydimethylsilyl](chloromethylsilyl)amine ([(CH3)2(OCH3)Si]2N-SiHCl(CH3)) were added, and then 6.23 g (0.78 mol) of lithium hydride (LiH) was slowly added at room temperature. The reaction solution was gradually heated to room temperature and stirred at room temperature for 18 hours. After the reaction was completed, the reaction mixture was filtered to remove lithium chloride (LiCl), the solvent was removed from the resulting filtrate under reduced pressure, and then distilled under reduced pressure to obtain 93.0 g (0.39 mol) of the title compound, bis[methoxydimethylsilyl](methylsilyl)amine ([(CH3)2(OCH3)Si]2N-SiH2(CH3)). (Yield 50.0%)

[0171] 1 H-NMR (C6D6): δ 4.68(m, 2H (SiH2(CH3)), δ 3.28(s, 6H (CH3)2(OCH3)Si, δ 0.29(t, 3H (SiH2(CH3)), δ 0.24(s, 12H [(CH3)2(OCH3)Si]2N)

[0172] 29 Si-NMR (C6D6): δ-33.0 (SiH2(CH3)) δ0.98 ([(CH3)2(OCH3)Si]2N)

[0173] From FIG. 1 and FIG. 2, it was confirmed that the alkoxyaminosilylamine compound precursor manufactured by the above method had high volatility, stability, and thermal decomposition characteristics.

[0174] While specific aspects of the present invention have been described in detail above, it will be apparent to those skilled in the art that these specific descriptions merely represent preferred embodiments and are not intended to limit the scope of the present invention. Therefore, the substantial scope of the present invention is defined by the appended claims and their equivalents.

Claims

1. Alkoxyaminosilylamine compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R 1 Inland R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen; R 5 Inland R 8 are independently C1-C10 alkyl.

2. In paragraph 1, R 1 Inland R 4 are independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl or halogen; R 5 Inland R 8 An alkoxyaminosilylamine compound, which is independently C1-C5 alkyl.

3. In paragraph 1, R 1 Inland R 4 are independently hydrogen or C1-C5 alkyl; R 5 Inland R 8 An alkoxyaminosilylamine compound, which is independently C1-C5 alkyl.

4. In paragraph 1, An alkoxyaminosilylamine compound selected from the following compounds. A method for producing an alkoxyaminosilylamine compound, comprising the step of producing an alkoxyaminosilylamine compound of the following formula 1 by reacting a compound of the following formula 3 and a compound of the following formula 4 under a C1-C5 alkyl lithium. [Chemical Formula 1] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 1, 3 and 4, R 1 Inland R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen; R 5 Inland R 8 are independently C1-C10 alkyl; X is a halogen. A method for producing an alkoxyaminosilylamine compound, comprising: a step of reacting a compound of formula 4 below with a compound of formula 5 under a C1-C5 alkyl lithium to produce a compound of formula 6 below; a step of adding a reducing agent to the compound of formula 6 below to produce an alkoxyaminosilylamine compound of formula 1-1 below; [Chemical Formula 1-1] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] In the above chemical formulas 1-1, 4, 5 and 6, R 1 , R 3 and R 4 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen; R 5 Inland R 8 are independently C1-C10 alkyl; X is a halogen.

7. A composition for thin film deposition containing silicon, comprising an alkoxyaminosilylamine compound represented by the following chemical formula 2. [Chemical Formula 2] In the above chemical formula 2, R 9 Inland R 13 are independently hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen; R 14 Inland R 17 are independently C1-C10 alkyl.

8. In paragraph 7, R 9 Inland R 13 are independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl or halogen; R 14 Inland R 17 A composition for thin film deposition containing silicon, wherein each independently is C1-C5 alkyl.

9. A composition for thin film deposition containing silicon, wherein in the 7th paragraph, the chemical formula 2 is selected from the following compounds.

10. A method for manufacturing a silicon-containing thin film, comprising manufacturing a thin film using a silicon-containing thin film deposition compound selected from any one of claims 1 to 4.

11. A method for producing a silicon-containing thin film, comprising producing a thin film using a silicon-containing thin film deposition composition selected from any one of claims 7 to 9.

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