Novel alkoxyaminosilylamine compounds, methods for producing the same, silicon-containing thin film deposition compositions containing the same, and methods for producing silicon-containing thin films using the same.
Thermally stable alkoxyaminosilylamine compounds address the limitations of existing silicon precursors by enabling the formation of high-purity, high-quality silicon-containing thin films with improved reactivity and thermal stability, suitable for diverse temperature applications.
Patent Information
- Application Number
- JP2026507426
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-09-12
- Filing Date
- 2024-08-29
- Publication Date
- 2026-08-26
AI Technical Summary
Existing silicon precursors face challenges in forming ultrafine thin films with uniform thickness and excellent electrical properties at low temperatures, particularly due to high-temperature processes, step coverage issues, and etching characteristics, which are not adequately addressed by current silanes, silane chlorides, and aminosilanes.
Development of thermally stable and highly volatile alkoxyaminosilylamine compounds, represented by specific chemical structures, which serve as precursors for silicon-containing thin films, enabling stable film formation over a wide temperature range with improved reactivity.
The alkoxyaminosilylamine compounds facilitate the production of high-purity, high-quality silicon-containing thin films with excellent thermal stability and durability, offering enhanced reactivity and deposition rates.
Smart Images

Figure 2026528906000001_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a novel alkoxyaminosilylamine compound, a method for producing the same, a composition for depositing a silicon-containing thin film containing the same, and a method for producing a silicon-containing thin film using the same.
Background Art
[0002] Silicon-containing thin films are produced into various forms 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 used in thin film transistors (TFTs), solar cells, etc., and their application fields are gradually diversifying.
[0003] For the production of thin films containing silicon, there are a chemical vapor deposition method (MOCVD) in which a silicon precursor in gaseous form and a reaction gas react to form a film on the surface of a substrate or react directly on the surface to form a film, and an atomic layer deposition method (ALD) in which a silicon precursor in gaseous form is physically or chemically adsorbed on the surface of the substrate and then a film is formed by sequentially introducing a reaction gas. Various thin film production technologies such as a low-pressure chemical vapor deposition method (LPCVD) applying this, a chemical vapor deposition method (PECVD) using plasma capable of depositing at low temperature, and an atomic layer deposition method (PEALD) are applied to the production processes of next-generation semiconductors and display elements and are used for the formation of ultra-fine patterns and the deposition of extremely thin films having uniform and excellent characteristics with a thickness in the nanometer unit.
[0004] The precursors used for forming silicon-containing thin films are typically compounds in the form of silanes, silane chlorides, aminosilanes, and alkoxysilanes. Specific examples include silane chloride compounds such as dichlorosilane (SiH2Cl2) and hexachlorodisilane (Cl3SiSiCl3), as well as trisilylamine (N(SiH3)3), bis-diethylaminosilane (H2Si(N(CH2CH3)2)2), and di-isopropylaminosilane (H3SiN(i-C3H7)2), which are used in the mass production processes of semiconductors and displays.
[0005] However, due to the miniaturization of devices resulting from ultra-high integration, the increase in aspect ratio, and the diversification of device materials, there is a need for technology to form ultrafine thin films with uniform thickness and excellent electrical properties at desired low temperatures. Existing silicon precursors present challenges in high-temperature processes above 600°C, step coverage, etching characteristics, and the physical and electrical properties of the thin films. Therefore, the development of superior novel silicon precursors is required. [Overview of the project] [Problems that the invention aims to solve]
[0006] The present invention aims to provide novel alkoxyaminosilylamine compounds and methods for producing the same.
[0007] More specifically, one objective of the present invention is to provide a thermally stable and highly volatile alkoxyaminosilylamine compound that is useful as a precursor for the formation of silicon-containing thin films.
[0008] Specifically, an 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 in a wide temperature range.
[0009] The present invention also provides a composition for depositing a silicon-containing thin film, which contains an alkoxyaminosilylamine compound according to an embodiment of the present invention.
[0010] The present invention also provides a method for forming a silicon-containing thin film with excellent properties, using the alkoxyaminosilylamine compound or the composition for depositing a silicon-containing thin film containing the same.
Means for Solving the Problems
[0011] The present invention provides an alkoxyaminosilylamine compound represented by the following Chemical Formula 1.
Chem.
[0013] , , 1 , 5 , 1 , , 5 , 1 , , , 5 ,
[0012] ~R 4 are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl or halogen, R 5 ~R 8 are, independently of each other, C1-C10 alkyl.
[0012] In the compound according to an embodiment, in the Chemical Formula 1, R 1 ~R 4 are, independently of each other, hydrogen, C1-C5 alkyl, C2-C5 alkenyl or halogen, and R 5 ~R 8 may be, independently of each other, C1-C5 alkyl.
[0013] In the compound according to an embodiment, in the Chemical Formula 1, R 1 ~R 4 are, independently of each other, hydrogen or C1-C5 alkyl, R 5 ~R8 These may be C1-C5 alkyl groups, independently of each other.
[0014] A compound according to one embodiment is R in the chemical formula 1. 1 ~R 4 R is independently of hydrogen, C1-C3 alkyl, C2-C4 alkenyl, or halogen. 5 ~R 8 These may be C1-C3 alkyl groups, independently of each other.
[0015] A compound according to one embodiment is R in the chemical formula 1. 1 ~R 4 R is independently of hydrogen or a C1-C3 alkyl group. 5 ~R 8 These may be C1-C3 alkyl groups, independently of each other.
[0016] In one embodiment, the aforementioned chemical formula 1 may be at least one selected from the following structures. [ka]
[0017] Furthermore, the present invention provides a method for producing an alkoxyaminosilylamine compound, which includes the step of reacting a compound of chemical formula 3 and a compound of chemical formula 4 under C1-C5 alkyllithium to produce an alkoxyaminosilylamine compound of chemical formula 1. [ka] In the aforementioned chemical formulas 1, 3, and 4, R 1 ~R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 8 These are, independently of each other, C1-C10 alkyl groups. X is a halogen.
[0018] A method for producing an alkoxyaminosilylamine compound according to one embodiment may include the steps of: reacting the compound of chemical formula 4 with chemical formula 5 under C1-C5 alkyllithium to produce the compound of chemical formula 6; and adding a reducing agent to chemical formula 6 to produce the alkoxyaminosilylamine compound of chemical formula 1-1. [ka] In the aforementioned chemical formulas 1-1, 4, 5, and 6, R 1 , R 3 and R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 8 These are, independently of each other, C1-C10 alkyl groups. X is a halogen.
[0019] Furthermore, the present invention provides a silicon-containing thin film deposition composition comprising an alkoxyaminosilylamine compound represented by the following chemical formula 2. [ka] In the aforementioned chemical formula 2, R 9 ~R 13 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 14 ~R 17 These are C1-C10 alkyl groups, independently of each other.
[0020] A silicon-containing thin film deposition composition according to one embodiment, in the chemical formula 2, R 9 ~R 13 R is independently of hydrogen, C1-C5 alkyl, C2-C5 alkenyl, or halogen. 14 ~R 17 These may be C1-C5 alkyl groups, independently of each other.
[0021] In one embodiment, the chemical formula 2 may be at least one selected from the following structures. [ka]
[0022] Furthermore, the present invention provides a method for producing a silicon-containing thin film using an alkoxyaminosilylamine compound according to one embodiment.
[0023] Furthermore, the present invention provides a method for producing a silicon-containing thin film using a silicon-containing thin film deposition composition according to one embodiment. [Effects of the Invention]
[0024] The alkoxyaminosilylamine compound according to the present invention is provided as a precursor for a thermally stable and highly volatile silicon-containing thin film, and can form a silicon-containing thin film with excellent properties.
[0025] Furthermore, the alkoxyaminosilylamine compound according to the present invention can exhibit excellent reactivity over a wide temperature range when used to produce silicon-containing thin films.
[0026] Furthermore, the silicon-containing thin film deposition composition according to one embodiment of the present invention, by containing an alkoxyaminosilylamine compound according to one embodiment of the present invention, can produce a high-quality silicon-containing thin film.
[0027] Furthermore, the method for producing alkoxyaminosilylamine compounds according to one embodiment of the present invention can produce high-purity alkoxyaminosilylamine compounds in high yield. [Brief explanation of the drawing]
[0028] [Figure 1] This is a thermogravimetric (TGA) graph of the alkoxyaminosilylamine compounds prepared in Examples 1 and 2. [Figure 2]This is a differential scanning calorimetry (DSC) graph of the alkoxyaminosilylamine compounds prepared in Examples 1 and 2. [Modes for carrying out the invention]
[0029] The present invention will now be described in more detail. Unless otherwise defined, technical and scientific terms used herein have the meaning that is ordinarily understood by a person with ordinary skill in the art to which the present invention belongs. In the following description, explanations of known functions and configurations that may obscure the gist of the present invention will be omitted.
[0030] In this specification, the term "CA-CB" means "the number of carbon atoms is between A and B," and the term "A-B" means "the number of carbon atoms is between A and B."
[0031] As used herein, the term "alkyl" refers to a monovalent substituted compound, encompassing all linear or branched forms.
[0032] The alkyl group may have 1 to 10 carbon atoms, specifically 1 to 5 carbon atoms, and more specifically 1 to 3 carbon atoms.
[0033] The alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, and hexyl, as examples.
[0034] As used herein, the term "alkoxy" 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, and t-butoxy.
[0035] As used herein, the term "alkenyl" means a hydrocarbon in a linear or branched form having at least one carbon-carbon double bond.
[0036] The alkenyl may have 2 to 10 carbon atoms, specifically 2 to 7, and more specifically 2 to 5 carbon atoms.
[0037] The aforementioned alkenyls include, but are not limited to, vinyl, silyl, butenyl, isobutenyl, pentenyl, and hexenyl.
[0038] In this specification, the term "halogen" means a Group 17 element, which may be any one selected from F, Cl, Br, or I.
[0039] Furthermore, the term "includes" in this specification is an open-ended expression equivalent to "equipped with," "contains," "possesses," or "characterizes," and does not exclude any elements, materials, or processes not listed.
[0040] Furthermore, the singular form used herein may also include the plural form unless otherwise specified in the context.
[0041] In this specification, the term "thermal stability" may mean that the physical properties do not change during a continuous heating process or a high-temperature process, and more specifically, that the material does not undergo structural changes even when exposed for a long period of time under the harsh conditions described above.
[0042] In this specification, the term "silicon-containing thin film with superior properties" refers to a high-quality silicon-containing thin film with a high silicon content and excellent thermal stability and durability.
[0043] In this specification, "normal temperature" may mean the temperature in a state where no artificial temperature control is performed, and for example, the normal temperature may be 20°C to 40°C, 20°C to 30°C, or 23°C to 26°C.
[0044] The present invention provides a novel alkoxyaminosilylamine compound useful as a precursor for producing silicon-containing thin films, the alkoxyaminosilylamine compound of the present invention is represented by the following chemical formula 1.
[0045] [ka]
[0046] In the aforementioned chemical formula 1, R 1 ~R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 6 These are C1-C10 alkyl groups, independently of each other.
[0047] The alkoxyaminosilylamine compound of the present invention has a structure in which an alkoxy functional group is introduced to a silicon atom in a trisilylamine structure. The alkoxy functional group introduced to the silicon atom has a lower activation energy, improving reactivity, and does not generate non-volatile byproducts, allowing for the easy formation of high-purity silicon-containing thin films with a high deposition rate.
[0048] In one embodiment of an alkoxyaminosilylamine compound, in the chemical formula 1, R 1 ~R 4 R is independently of hydrogen, C1-C5 alkyl, C2-C5 alkenyl, or halogen. 5 ~R 8 These may be C1-C5 alkyl groups, independently of each other.
[0049] In one embodiment of an alkoxyaminosilylamine compound, in the chemical formula 1, R 1 ~R 4 R is independently of hydrogen or a C1-C5 alkyl group. 5 ~R 8 These may be C1-C5 alkyl groups, independently of each other.
[0050] In one embodiment of an alkoxyaminosilylamine compound, in the chemical formula 1, R 1 ~R 4R is independently of hydrogen, C1-C3 alkyl, C2-C4 alkenyl, or halogen. 5 ~R 8 These may be C1-C3 alkyl groups, independently of each other.
[0051] In one embodiment of an alkoxyaminosilylamine compound, in the chemical formula 1, R 1 ~R 4 R is independently of hydrogen or a C1-C3 alkyl group. 5 ~R 8 These may be C1-C3 alkyl groups, independently of each other.
[0052] In one specific example, the aforementioned chemical formula 1 may be selected from, but is not limited to, the following compounds.
[0053] [ka]
[0054] Furthermore, the present invention provides a method for producing the alkoxyaminosilylamine compound.
[0055] In one embodiment, a method for producing an alkoxyaminosilylamine compound is provided, which includes the step of reacting a compound of chemical formula 3 and a compound of chemical formula 4 under a C1-C5 alkyllithium under conditions to produce an alkoxyaminosilylamine compound of chemical formula 1.
[0056] [ka]
[0057] [ka]
[0058] [ka]
[0059] In the aforementioned chemical formulas 1, 3, and 4, R 1 ~R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 8 These are, independently of each other, C1-C10 alkyl groups. X is a halogen.
[0060] In the above-mentioned manufacturing method, alkyllithium is a compound in which lithium is bonded to a C1-C5 alkyl group, and specifically may be methyllithium, ethyllithium, or n-butyllithium, and preferably n-butyllithium.
[0061] In the above manufacturing method, the halogen may be any one halogen selected from F, Cl, Br, and I, and preferably, X may be Cl.
[0062] A method for producing an alkoxyaminosilylamine compound according to one embodiment may include the steps of: reacting the compound of chemical formula 4 with chemical formula 5 under C1-C5 alkyllithium to produce the compound of chemical formula 6; and adding a reducing agent to chemical formula 6 to produce the alkoxyaminosilylamine compound of chemical formula 1-1.
[0063] [ka]
[0064] [ka]
[0065] [ka]
[0066] [ka]
[0067] In the aforementioned chemical formulas 1-1, 4, 5, and 6, R 1 , R 3 and R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 8 These are, independently of each other, C1-C10 alkyl groups. X is a halogen.
[0068] In the above-mentioned manufacturing method, alkyllithium is a compound in which lithium is bonded to a C1-C5 alkyl group, and specifically may be methyllithium, ethyllithium, or n-butyllithium, and preferably n-butyllithium.
[0069] In the above manufacturing method, the halogen may be any one halogen selected from F, Cl, Br, and I, and preferably, X may be Cl.
[0070] In the above-mentioned manufacturing method, the reducing agent can preferably be a compound capable of introducing hydrogen into the product through the reaction. Specifically, it may be a metal hydride capable of providing hydrogen, and as an example, it may be one or more 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. Since the reducing agent is added to the chemical formula 6, it is preferable that it can substitute the halogen atom of the chemical formula 6 with hydrogen.
[0071] According to one embodiment, all of the above reactions can be carried out in an organic solvent, specifically, one or more mixed organic solvents selected from hexane, diethyl ether, toluene, tetrahydrofuran, etc., can be used, but are not limited thereto.
[0072] Furthermore, in all of the above reactions, the reaction temperature can be the same as that used in ordinary organic synthesis, but it may vary depending on the reaction time and the amounts of reactants and starting materials.
[0073] After the reaction, the purity can be increased by removing by-products through filtration, extraction, recrystallization, distillation, sublimation, chromatography, etc.
[0074] The alkoxyaminosilylamine compound produced by the above method is not only thermally stable, highly volatile, and suitable for forming silicon-containing thin films with excellent properties, but also exhibits excellent reactivity over a wide temperature range, enabling the stable production of silicon-containing thin films.
[0075] Furthermore, the method for producing the alkoxyaminosilylamine compound described above makes it possible to produce a high-purity alkoxyaminosilylamine compound in high yield.
[0076] Furthermore, the present invention provides a silicon-containing thin film deposition composition comprising a compound represented by the following chemical formula 2.
[0077] [ka]
[0078] In the above chemical formula 2, R 9 ~R 13 R is independently of hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. 14 ~R 17 These are C1-C10 alkyl groups, independently of each other.
[0079] A silicon-containing thin film deposition composition according to one embodiment, in the chemical formula 2, R 9 ~R 13 R is independently of hydrogen, C1-C5 alkyl, C2-C5 alkenyl, or halogen. 14 ~R 17 These may be C1-C5 alkyl groups, independently of each other.
[0080] A silicon-containing thin film deposition composition according to one embodiment, in the chemical formula 2, R 9 ~R 13 R is independently of each other: hydrogen, C1-C3 alkyl, C2-C3 alkenyl, or halogen. 14 ~R 17 These may be C1-C3 alkyl groups, independently of each other.
[0081] The alkoxyaminosilylamine compound contained 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 in a trisilylamine structure. The alkoxy functional group introduced to the silicon atom has a lower activation energy and improved reactivity, does not generate non-volatile byproducts, and allows for the easy formation of high-purity silicon-containing thin films with a high deposition rate.
[0082] Furthermore, due to its high silicon atom content within the molecule, this silicon-containing thin film deposition composition not only allows for the easy deposition of high-quality silicon-containing thin films with a high deposition rate, but also enables the production of thin films with excellent thermal stability, high durability, and superior purity.
[0083] The silicon-containing thin film deposition composition of the present invention can be included within a content range that is recognizable to those skilled in the art, taking into consideration the thin film deposition conditions, thin film thickness, properties, etc.
[0084] In one specific example, the aforementioned chemical formula 2 can be selected from the following structures, but is not limited thereto.
[0085] [ka]
[0086] Furthermore, the present invention provides a method for producing a silicon-containing thin film using the above-mentioned alkoxyaminosilylamine compound or silicon-containing thin film deposition composition.
[0087] In one embodiment, a method for producing a silicon-containing thin film involves producing a silicon-containing thin film deposition composition containing the thermally stable and highly volatile alkoxyaminosilylamine compound as a precursor, thereby enabling the production of a silicon-containing thin film with excellent properties.
[0088] The method for producing a silicon-containing thin film according to one embodiment can be any method that is within the scope of what a person skilled in the art can recognize, and is preferably carried out by atomic layer deposition (ALD), chemical vapor deposition (CVD), metal-organic chemical vapor deposition (MOCVD), low-pressure chemical vapor deposition (LPCVD), plasma-enhanced chemical vapor deposition (PECVD), or plasma-enhanced atomic layer deposition (PEALD). Plasma-enhanced atomic layer deposition (PEALD) or plasma-enhanced chemical vapor deposition (PECVD) is preferred in terms of easier thin film deposition and the resulting thin film having superior properties.
[0089] A specific example of a method for manufacturing a silicon-containing thin film may include the steps of: a) heating and maintaining a substrate mounted in a chamber at a temperature of 30 to 400°C; b) contacting a silicon-containing thin film deposition composition according to one embodiment with the substrate and allowing it to be adsorbed; and c) injecting a reaction gas to deposit a silicon-containing thin film onto the substrate.
[0090] Preferably, when a silicon-containing thin film according to one specific example of the present invention is deposited by plasma-enhanced atomic layer deposition (PEALD) or plasma-enhanced chemical vapor deposition (PECVD), the process may further include a step of generating plasma after step a). Also, in step b), the silicon-containing thin film deposition composition according to one embodiment may be injected together with a carrier gas.
[0091] In one embodiment of the method for producing a silicon-containing thin film, the deposition conditions can be adjusted according to the structure or thermal properties of the target thin film. Examples of deposition conditions in one specific example include the input flow rate of the silicon-containing thin film deposition composition containing an alkoxyaminosilylamine compound, the input flow rates of the reaction gas and carrier gas, pressure, RF power, and substrate temperature. A non-limiting example of such deposition conditions is that the input flow rate of the silicon-containing thin film deposition composition can be adjusted to 10-1000 cc / min, the carrier gas to 10-1000 cc / min, the reaction gas to 1-1000 cc / min, the pressure to 0.5-10 torr, the RF power to 200-1000 W, and the substrate temperature to 30-400°C, preferably to 100-350°C, but is not limited to these conditions.
[0092] The silicon-containing thin film according to one embodiment can be any thin film that can be manufactured within the scope recognized by a person skilled in the art in this field. Specifically, it 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 various other high-quality thin films containing silicon can be manufactured within the scope recognized by a person skilled in the art.
[0093] The reaction gas used in the method for producing a silicon-containing thin film according to one embodiment can be any gas that is normally used with a silicon precursor, taking into consideration the material of the silicon-containing thin film to be produced. Specific examples include one or more selected from oxygen (O2), ozone (O3), distilled water (H2O), hydrogen peroxide (H2O2), nitric oxide (NO), nitrous oxide (N2O), nitrogen dioxide (NO2), ammonia (NH3), nitrogen (N2), hydrazine (N2H4), amines, diamines, carbon monoxide (CO), carbon dioxide (CO2), C1-C12 saturated or unsaturated hydrocarbons, hydrogen, argon, and helium. The carrier gas may be one or more selected from argon, helium, and nitrogen, but is not limited to these.
[0094] 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 containing one or more semiconductor materials from among Si, Ge, SiGe, GaP, GaAs, SiC, SiGeC, InAs, and InP, an SOI (Silicon On Insulator) substrate, a quartz substrate, a display glass substrate, a flexible plastic substrate such as polyimide, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polymethyl methacrylate (PMMA), polycarbonate (PC), polyethersulfone (PES), or polyester.
[0095] In addition, the silicon-containing thin film may be formed not only by directly forming it on the substrate, but also by forming a number of conductive layers, dielectric layers, or insulating layers between the substrate and the silicon-containing thin film.
[0096] The following describes embodiments of the present invention in detail. However, these are provided so that they can be easily implemented by a person with ordinary skill in the art to which the present invention belongs, and the present invention can be realized in a variety of different forms, and the spirit of the present invention is not necessarily limited to these embodiments.
[0097] The following describes the alkoxyaminosilylamine compound according to one embodiment of the present invention. 1 1H NMR, 13 1C NMR and 29 The structure was analyzed using Si-NMR spectroscopy.
[0098] Furthermore, the thermal stability, volatility, and decomposition temperature of alkoxyaminosilylamine compounds were measured using thermogravimetric analysis (TGA) and differential scanning calorimeter (DSC).
[0099] [Example 1] Synthesis of bis[dimethylmethoxysilyl](dimethylsilyl)amine [ka]
[0100] In a 2 L flask, flame-dried under anhydrous and inert atmosphere, add hexane (C6H 14 After adding 206 g (2.39 mol) of bis(methoxydimethylsilyl)amine ([(CH3)2(OCH3)Si]2NH) and 71.3 g (0.37 mol), n-butyllithium (2.68 M, 137.8 ml) was slowly added while maintaining the internal temperature at -20°C. After the reaction was completed, the temperature of the reaction solution was gradually raised to room temperature and stirred at room temperature for 4 hours. The mixture was then heated in a 2 L flask (flask) and flame-dried under anhydrous and inert atmosphere, and hexane (C6H 14After adding 95.3 g (1.11 mol) of bis(methoxydimethylsilyl)amine ((CH3)2ClSiH) and 34.9 g (0.37 mol) of chlorodimethylsilane ((CH3)2ClSiH), 73.5 g (0.37 mol) of the resulting lithium bis(methoxydimethylsilyl)amine salt ([(CH3)2(OCH3)Si]2NLi) was slowly added while maintaining the temperature at -20°C. The reaction solution was then gradually heated to room temperature and stirred for 4 hours. After the reaction was complete, the reaction mixture was filtered to remove lithium chloride (LiCl), and the solvent was removed from the resulting filtrate under reduced pressure. The title compound, bis[methoxydimethylsilyl](dimethylsilyl)amine ([(CH3)2(OCH3)Si]2N-SiH(CH3)2), was obtained by vacuum distillation. (Yield 57.9%)
[0101] 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)
[0102] 29 Si-NMR (C6D6) : δ-13.71 (SiH(CH3)2) δ1.34 ([(CH3)2(OCH3)Si]2N)
[0103] [Example 2] Synthesis of bis[dimethylmethoxysilyl](methylsilyl)amine [ka]
[0104] In a 2 L flask, flame-dried under anhydrous and inert atmosphere, add hexane (C6H 14After adding 379.3 g (4.40 mol) of bis(methoxydimethylsilyl)amine ([(CH3)2(OCH3)Si]2NH) and 170.3 g (0.88 mol), n-butyllithium (2.60 M, 339.5 ml) was slowly added while maintaining the internal temperature at -20°C, and the mixture was stirred at room temperature for 4 hours to produce 175.5 g (0.88 mol) of bis(methoxydimethylsilyl)amine lithium salt ([(CH3)2(OCH3)Si]2NLi).
[0105] In a flame-dried 3L flask under an anhydrous and inert atmosphere, add hexane (C6H 14 After adding 227.6 g (2.64 mol) of bis(methoxydimethylsilyl)amine and 101.3 g (0.88 mol) of dichloromethylsilane ((CH3)Cl2SiH), 175.5 g (0.88 mol) of bis(methoxydimethylsilyl)amine lithium salt ([(CH3)2(OCH3)Si]2NLi), which was prepared while maintaining the temperature at -20°C, was slowly added. After the reaction was completed, the temperature of the reaction solution was gradually raised to room temperature and stirred at room temperature for 4 hours. After the reaction was complete, the reaction mixture was filtered to remove lithium chloride salt (LiCl), and the solvent was removed from the obtained filtrate under reduced pressure. Then, bis[methoxydimethylsilyl](chloromethylsilyl)amine ([(CH3)2(OCH3)Si]2N-SiHCl(CH3)) was obtained by vacuum distillation. (Yield 88.6%)
[0106] In a flame-dried 1 L flask under 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. Then, 6.23 g (0.78 mol) of lithium hydride (LiH) was slowly added at room temperature. The reaction solution was then gradually heated to room temperature and stirred for 18 hours. After the reaction was complete, the reaction mixture was filtered to remove lithium chloride (LiCl), and the solvent was removed from the resulting filtrate under reduced pressure. The title compound, bis[methoxydimethylsilyl](methylsilyl)amine ([(CH3)2(OCH3)Si]2N-SiH2(CH3)), was obtained by vacuum distillation. (Yield 50.0%)
[0107] 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) 29 Si-NMR (C6D6) : δ-33.0 (SiH2(CH3)) δ0.98 ([(CH3)2(OCH3)Si]2N)
[0108] Figures 1 and 2 confirm the high volatility, stability, and thermal decomposition properties of the alkoxyaminosilylamine compound precursor produced by the above method.
[0109] Having described in detail certain aspects of the present invention, it goes without saying that such specific descriptions are merely preferred embodiments and do not limit the scope of the invention to those with ordinary skill in the art. Therefore, the substantial scope of the present invention is defined by the appended claims and their equivalents.
Claims
1. An alkoxyaminosilylamine compound represented by the following chemical formula 1. 【Chemistry 1】 In the aforementioned chemical formula 1, R 1 ~R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 8 These are C1-C10 alkyl groups, independently of each other.
2. R 1 ~R 4 These are, independently of each other, hydrogen, C1-C5 alkyl, C2-C5 alkenyl, or halogen. R 5 ~R 8 The alkoxyaminosilylamine compound according to claim 1, wherein each of the elements is independently a C1-C5 alkyl group.
3. R 1 ~R 4 are, independently of one another, hydrogen or C1-C5 alkyl, R 5 ~R 8 The alkoxyaminosilylamine compound according to claim 1, wherein each of the elements is independently a C1-C5 alkyl group.
4. An alkoxyaminosilylamine compound according to claim 1, selected from the following compounds. 【Chemistry 2】
5. A method for producing an alkoxyaminosilylamine compound, comprising the step of reacting a compound of the following chemical formula 3 and a compound of the following chemical formula 4 under a C1-C5 alkyllithium atmosphere to produce an alkoxyaminosilylamine compound of the following chemical formula 1. 【Transformation 3】 In the aforementioned chemical formulas 1, 3, and 4, R 1 ~R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 8 These are, independently of each other, C1-C10 alkyl groups. X is a halogen.
6. A method for producing an alkoxyaminosilylamine compound, comprising the steps of: reacting a compound of the following chemical formula 4 with a compound of the following chemical formula 5 under a C1-C5 alkyllithium under conditions to produce a compound of the following chemical formula 6; and adding a reducing agent to the following chemical formula 6 to produce an alkoxyaminosilylamine compound of the following chemical formula 1-1. 【Chemistry 4】 In the aforementioned chemical formulas 1-1, 4, 5, and 6, R 1 , R 3 and R 4 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 5 ~R 8 These are, independently of each other, C1-C10 alkyl groups. X is a halogen.
7. A silicon-containing thin film deposition composition comprising an alkoxyaminosilylamine compound represented by the following chemical formula 2. 【Transformation 5】 In the aforementioned chemical formula 2, R 9 ~R 13 These are, independently of each other, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, or halogen. R 14 ~R 17 These are C1-C10 alkyl groups, independently of each other.
8. R 9 ~R 13 These are, independently of each other, hydrogen, C1-C5 alkyl, C2-C5 alkenyl, or halogen. R 14 ~R 17 The silicon-containing thin film deposition composition according to claim 7, wherein each of the elements is independently a C1-C5 alkyl group.
9. The above chemical formula 2 is selected from the following compounds, wherein this is the silicon-containing thin film deposition composition according to claim 7. 【Transformation 6】
10. A method for producing a silicon-containing thin film, comprising producing a thin film using a silicon-containing thin film deposition compound according to any one of claims 1 to 4.
11. A method for producing a silicon-containing thin film, comprising producing a thin film using the silicon-containing thin film deposition composition described in any one of claims 7 to 9.