Aminoalkoxydisilazane compound, composition for silicon-containing thin film deposition comprising same, and method for preparing silicon-containing thin film using same

Abstract

The present invention relates to an aminoalkoxydisilazane compound, 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, the aminoalkoxydisilazane compound of the present invention being capable of using a silicon-containing precursor as a thermally stable compound having high volatility and reactivity, therefore, a high-purity silicon-containing thin film having excellent physical and electrical characteristics can be formed by various deposition methods.

Description

Technical Field

[0001] The present invention relates to an aminoalkoxydisilazane compound, a composition for depositing a silicon-containing thin film including the same, and a method for preparing a silicon-containing thin film using the same. Background Art

[0002] Silicon-containing thin films are essential materials in semiconductor manufacturing and are used in various forms such as silicon films, silicon oxide films, silicon nitride films, silicon carbonitride films, and silicon oxynitride films. These thin films play a necessary role in advanced electronic devices such as memories, logic chips, flat panel displays (TFTs), and solar cells, and are used as semiconductor substrates, diffusion masks, antioxidant films, and dielectric films. In recent years, polycrystalline silicon thin films have been applied to various fields such as solar cells, and their utilization rate has been increasing.

[0003] To deposit silicon-containing thin films, various silicon precursors (such as aminosilanes and alkoxysilanes) including existing silicon precursors (such as silane, disilane, and halogenated silanes) are being developed, and representative processes include chemical vapor deposition (CVD) and atomic layer deposition (ALD). In particular, ALD is very effective in forming ultrathin films with uniform thickness, so it is an essential process for realizing fine patterns in the latest semiconductor devices. In addition, deposition techniques using plasma (PECVD and PEALD) can deposit thin films under low-temperature conditions, so they have become important techniques for fabricating new-generation semiconductors and display elements.

[0004] In recent years, the miniaturization and high integration of ultrathin semiconductor devices have been rapidly progressing, and the requirements for silicon precursors have become more stringent. The precursor should be stable at room temperature and have high volatility, have no non-volatile by-products during the thin film deposition process, have significant thermal stability and reactivity at high temperature, and be easy to handle, transport, and store. To deposit high-quality thin films, precursors with these characteristics are necessary.

[0005] Due to the development of ultra-high integration semiconductor devices, existing precursors have limitations in forming uniform thin films under low-temperature conditions, and problems such as reduced production capacity and physical electrical property problems also occur. Therefore, there is a need to develop a new silicon precursor that can deposit rapidly and uniformly at low temperature and has excellent physical properties.

[0006] Prior Art Documents

[0007] Patent Documents

[0008] Patent Document 1: KR10-2023-0151303A (November 1, 2023) Summary of the Invention

[0009] Problems to be Solved by the Invention

[0010] In one aspect of the present invention, there is provided an aminoalkoxydisilazane compound and a composition for depositing a silicon-containing film containing the same, and the compound can be used as a precursor for a silicon film.

[0011] In another aspect of the present invention, there is provided a method for preparing a silicon-containing film using the aminoalkoxydisilazane compound or the composition for depositing a silicon-containing film containing the same.

[0012] Means for Solving the Problems

[0013] In one aspect of the present invention, there is provided an aminoalkoxydisilazane compound represented by the following Chemical Formula 1.

[0014] [Chemical Formula 1]

[0015]

[0016] In the Chemical Formula 1,

[0017] R 1 、R 11 and R 12 are each independently a C1-C7 alkyl group, a C3-C7 cycloalkyl group or a C2-C7 alkenyl group, or the R 11 and R 12 may be connected to each other to form a ring,

[0018] R 2 and R 3 are each independently a C1-C7 alkyl group, a C3-C7 cycloalkyl group or a C1-C7 alkoxy group,

[0019] R is a C1-C7 alkyl group or a C3-C7 cycloalkyl group,

[0020] R 4 and R 5 are each independently a C1-C7 alkyl group, a C3-C7 cycloalkyl group, a C1-C7 alkoxy group or a C3-C7 cycloalkyloxy group.

[0021] In another aspect of the present invention, there is provided a composition for depositing a silicon-containing film containing the aminoalkoxydisilazane compound according to the above aspect.

[0022] In still another aspect of the present invention, there is provided a method for preparing a silicon-containing film using the aminoalkoxydisilazane compound according to the above aspect or the composition for depositing a silicon-containing film containing the same.

[0023] Advantages of the Invention

[0024] The aminoalkoxydisilazane compound of the present invention has excellent volatility and thermal stability, exists in a liquid state under normal temperature and pressure conditions, is convenient for storage and handling, and has high reactivity. Therefore, it can be used as a precursor for depositing silicon-containing thin films to form high-purity and high-quality silicon-containing thin films.

[0025] Using the aminoalkoxydisilazane compound of the present invention as a precursor for thin film deposition, a high-quality silicon-containing thin film with a high silicon content, remarkable thermal stability and durability can be prepared.

[0026] In addition, the silicon-containing thin film prepared from the aminoalkoxydisilazane compound of the present invention not only has excellent chemical and thermal stability, but also has excellent durability and electrical properties. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 Shows the thermogravimetric analysis (TGA) results of ((dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine prepared in Example 1. DETAILED DESCRIPTION

[0028] In this specification, unless otherwise defined, all technical terms and scientific terms have the same meaning as commonly understood by those of ordinary skill in the technical field to which the present invention belongs. The terms used in this specification are only used to effectively describe specific specific examples and are not used to limit the present invention.

[0029] Unless otherwise specifically indicated in the context, the expression of a single quantity used in this specification may also include the expression of multiple quantities.

[0030] Throughout this specification, unless otherwise specifically described to the contrary, when referring to "including", "provided with", "containing" or "having" a certain component, it does not mean excluding other components, but may also include other components, and does not exclude additional unlisted elements, materials or processes.

[0031] The numerical ranges used in this specification include the lower limit value and the upper limit value and all values within that range, the increments logically derived from the form and width of the defined range, all values defined therein, and all possible combinations of the upper and lower limits of the numerical ranges defined in different forms. As an example, when the content of the composition is limited to 10% to 80% or 20% to 50%, the numerical ranges of 10% to 50% or 50% to 80% should also be interpreted as described in this specification. Unless otherwise specifically defined in this specification, values outside the numerical range that may occur due to experimental errors or rounding of values are also included in the defined numerical range.

[0032] Unless otherwise defined in this specification, "about" may be considered to be a value within 30%, 25%, 20%, 15%, 10% or 5% of a specified value.

[0033] Unless otherwise specifically mentioned, the units used in this specification are based on weight. As an example, the unit of "% " or "proportion" refers to "% by weight" or "weight ratio". Unless otherwise defined, "% by weight" refers to the weight percentage of any component in the entire composition in the composition.

[0034] The term "C A -C B " in this specification means "having A or more and B or less carbon atoms", and the term "A to B" means "A or more and B or less".

[0035] The term "alkyl" in this specification refers to a monovalent organic radical derived from a straight-chain or branched-chain saturated hydrocarbon and having 1 to 7, 1 to 5, 1 to 4 or 1 to 3 carbon atoms. For example, it may include methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, etc.

[0036] The term "cycloalkyl" in this specification refers to a monovalent saturated carbocyclic group composed of one or more rings. Examples of cycloalkyl radicals include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl, etc.

[0037] The term "alkenyl" in this specification refers to a straight-chain or branched-chain hydrocarbon group containing 2 to 7 carbon atoms and one or more carbon-carbon double bonds. Specifically, the alkenyl is a lower alkenyl radical having 2 to 7, 2 to 5, 2 to 4 or 2 to 3 carbon atoms. Examples of alkenyl radicals may include vinyl, propenyl, isopropenyl, allyl, butenyl, 4-methylbutenyl, etc. The alkenyl may include radicals having cis and trans orientations, or alternatively having E and Z orientations.

[0038] In this specification, "normal temperature" may refer to the temperature in a state where no artificial temperature control is performed. For example, the normal temperature may be 20 °C to 40 °C, or 20 °C to 30 °C, or 23 °C to 26 °C.

[0039] Hereinafter, the present invention will be described in detail. However, this is merely exemplary, and the present invention is not limited to the specific embodiments described exemplarily.

[0040] In one aspect of the present invention, there is provided an aminoalkoxydisilazane compound, which is used as a precursor for preparing a high-quality silicon-containing film. Specifically, the aminoalkoxydisilazane compound of one aspect is represented by the following Chemical Formula 1:

[0041] [Chemical Formula 1]

[0042]

[0043] In the formula (1),

[0044] R 1 、R 11 and R 12 are each independently a C1-C7 alkyl group, a C3-C7 cycloalkyl group or a C2-C7 alkenyl group, or the R 11 and R 12 may be connected to each other to form a ring,

[0045] R 2 and R 3 are each independently a C1-C7 alkyl group, a C3-C7 cycloalkyl group or a C1-C7 alkoxy group,

[0046] R is a C1-C7 alkyl group or a C3-C7 cycloalkyl group,

[0047] R 4 and R 5 are each independently a C1-C7 alkyl group, a C3-C7 cycloalkyl group, a C1-C7 alkoxy group or a C3-C7 cycloalkyloxy group.

[0048] On the one hand, the aminoalkoxysilazane compound has a disilazane skeleton of Si-N-Si, and has a structure in which an amino substituent is introduced on one Si and at least one alkoxy substituent is introduced on the other Si. On the one hand, the aminoalkoxysilazane compound may also have a lower activation energy and excellent thermal stability according to the above structural characteristics and the asymmetric structure of the silicon moieties existing on both sides centered on the central N of the disilazane skeleton. Therefore, the reactivity is significantly improved, and no non-volatile by-products are generated. Therefore, it is easy to form a high-quality silicon-containing film at a high deposition rate. On the one hand, the aminoalkoxysilazane compound exists in a liquid state at normal temperature and under the pressure conditions that can be processed, so it is easy to handle.

[0049] In one embodiment, in the formula (1), the R 1 、R 11 and R 12 may each independently be a C1-C5 alkyl group, a C3-C7 cycloalkyl group or a C2-C4 alkenyl group, or the R 11 and R 12 may be connected to each other through a C2-C7 alkylene group to form a ring, R 2 and R 3 may each independently be a C1-C5 alkyl group or a C3-C7 cycloalkyl group, R may be a C1-C5 alkyl group or a C3-C7 cycloalkyl group, R 4 and R 5Each independently may be a C1-C5 alkyl group, a C3-C7 cycloalkyl group or a C1-C5 alkoxy group.

[0050] As a specific example, in the said Chemical Formula 1, R 1 , R 11 and R 12 Each independently may be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C2-C3 alkenyl group, R 2 , R 3 and R each independently may be a C1-C4 alkyl group or a C3-C6 cycloalkyl group, R 4 may be a C1-C4 alkoxy group or a C3-C6 cycloalkyloxy group, R 5 may be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C1-C4 alkoxy group.

[0051] As a specific example, in the said Chemical Formula 1, R 1 may be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C2-C3 alkenyl group, R 11 and R 12 may be connected to each other through a C2-C6 alkylene group to form a ring, R 2 , R 3 and R each independently may be a C1-C4 alkyl group or a C3-C6 cycloalkyl group, R 4 and R 5 each independently may be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C1-C4 alkoxy group.

[0052] As a specific example, in the said Chemical Formula 1, R 1 , R 11 and R 12 each independently may be a C1-C4 alkyl group or a C2-C3 alkenyl group, R 2 , R 3 and R each independently may be a C1-C4 alkyl group, R 4 and R 5 each independently may be a C1-C4 alkyl group or a C1-C4 alkoxy group.

[0053] As a specific example, in the said Chemical Formula 1, R 1 , R 2 , R 3 , R, R 11 and R 12 each independently may be a C1-C4 alkyl group, R 4 and R 5 each independently may be a C1-C4 alkyl group or a C1-C4 alkoxy group.

[0054] In one embodiment, the aminoalkoxydisilazane compound may be represented by the following Chemical Formula 2 or Chemical Formula 3.

[0055] [Chemical formula 2]

[0056]

[0057] [Chemical formula 3]

[0058]

[0059] In the chemical formula 2 and the chemical formula 3,

[0060] R 1 , R 11 and R 12 Each is independently a C1-C4 alkyl, a C3-C6 cycloalkyl or a C2-C3 alkenyl,

[0061] R 2 , R 3 , R and R 4a Each is independently a C1-C4 alkyl group or a C3-C6 cycloalkyl group,

[0062] R 4 and R 5 Each is independently a C1-C4 alkyl, a C3-C6 cycloalkyl or a C1-C4 alkoxy group,

[0063] a is an integer of 0-4.

[0064] As a specific example, the R 1 , R 11 and R 12 Each independently may be a C1-C4 alkyl or a C2-C3 alkenyl, R 2 , R 3 , R and R 4a Each independently may be a C1-C4 alkyl group, R 4 and R 5 Each is independently a C1-C4 alkyl group or a C1-C4 alkoxy group, and a can be an integer from 0 to 3.

[0065] In one embodiment, the aminoalkoxydisilazane compound can be represented by the following Chemical Formula 4.

[0066] [Chemical formula 4]

[0067]

[0068] In the chemical formula 4,

[0069] R 1 is a C1-C4 alkyl group or a C2-C3 alkenyl group,

[0070] R 21 is a C1-C4 alkyl group,

[0071] R 22 is a C1-C4 alkyl group or a C1-C4 alkoxy group,

[0072] R is a C1-C4 alkyl group,

[0073] R 23 is a C1-C4 alkyl group or a C2-C3 alkenyl group.

[0074] As an example, the said R 1 can be a C1-C3 alkyl group or a C2-C3 alkenyl group. As a specific example, it can be methyl, ethyl, isopropyl, vinyl, isopropenyl or allyl.

[0075] As an example, the said R 21 can be a C1-C3 alkyl group. As a specific example, it can be methyl or ethyl.

[0076] As an example, the said R 22 can be a C1-C3 alkyl group or a C1-C3 alkoxy group, or can be a C1-C3 alkoxy group. As a specific example, it can be methyl, ethyl, methoxy or ethoxy.

[0077] As an example, the said R can be a C1-C3 alkyl group. As a specific example, it can be methyl or ethyl.

[0078] As an example, the said R 23 can be a C1-C3 alkyl group or a C2-C3 alkenyl group. As a specific example, it can be ethyl, isopropyl, vinyl, isopropenyl or allyl.

[0079] In one embodiment, the aminoalkoxy disilazane compound can be selected from the following compounds, but is not limited thereto.

[0080]

[0081] The above-mentioned aminoalkoxy disilazane compound can be prepared by possible methods within the scope recognizable by those of ordinary skill in the art.

[0082] On the other hand, the present invention provides a composition for depositing a silicon-containing film, and the composition contains the aminoalkoxy disilazane compound according to one aspect.

[0083] In one embodiment, the composition for depositing a silicon-containing thin film contains the aminoalkoxydisilazane compound having high volatility and excellent thermal stability as a precursor for thin film deposition, and its content can be included within a range recognizable by those of ordinary skill in the art by considering film formation conditions of the thin film, thickness and characteristics of the thin film, etc.

[0084] In another aspect of the present invention, there is provided a method for preparing a silicon-containing thin film, the preparation method including a step of depositing a silicon-containing thin film by using the aminoalkoxydisilazane compound represented by Chemical Formula 1 or a composition for depositing a silicon-containing thin film containing the same.

[0085] In one embodiment, in the method for preparing a silicon-containing thin film, by using the aminoalkoxydisilazane compound as a precursor, a high-quality silicon-containing thin film can be prepared at a high deposition rate under various conditions.

[0086] In one embodiment, the method for preparing a silicon-containing thin film can be used without limitation as long as it is a method possible within the range recognizable by those of ordinary skill in the art. For example, it can be carried out by atomic layer deposition (ALD), chemical vapor deposition (CVD), metalorganic chemical vapor deposition (MOCVD), low-pressure chemical vapor deposition (LPCVD), plasma-enhanced chemical vapor deposition (PECVD), or plasma-enhanced atomic layer deposition (PEALD).

[0087] In one embodiment, the aminoalkoxydisilazane compound and the reaction gas can each be supplied continuously or discontinuously, and the discontinuous supply may include a pulse form.

[0088] As an example, the method for preparing a silicon-containing thin film may include: Step a), maintaining the temperature of a substrate installed in a chamber at 100 °C or higher; Step b), adsorbing the aminoalkoxydisilazane compound according to one embodiment or a composition for depositing a silicon-containing thin film containing the same onto the substrate; and Step c), depositing a silicon-containing thin film by injecting a reaction gas onto the substrate on which the aminoalkoxydisilazane compound or the composition for depositing a silicon-containing thin film containing the same is adsorbed.

[0089] The method for preparing a silicon-containing thin film may further include a step of removing unreacted reactants by purge.

[0090] Specifically, the method for preparing the silicon-containing thin film may include: Step a) maintaining the temperature of a substrate installed in a chamber at 100°C to 700°C; Step b-1), adsorbing an aminoalkoxysilazane compound according to an embodiment or a composition for depositing a silicon-containing thin film containing the same onto the substrate; Step b-2), purging residual aminoalkoxysilazane compound or residual composition for thin film deposition and by-products; Step c-1), forming a silicon-containing thin film by injecting a reaction gas onto the substrate adsorbed with the aminoalkoxysilazane compound or the composition for thin film deposition containing the same; and Step c-2), purging residual reaction gas and by-products.

[0091] As an example, when the method for preparing the silicon-containing thin film is carried out by plasma-enhanced atomic layer deposition (PEALD) or plasma-enhanced chemical vapor deposition (PECVD), after the step a), it may further include: a step of generating plasma.

[0092] As an example, in the method for preparing the silicon-containing thin film, in the step b), the aminoalkoxysilazane compound or the composition for depositing a silicon-containing thin film containing the same may be injected together with a transfer gas.

[0093] By considering the type of the silicon-containing thin film to be prepared, any reaction gas that is usually used together with a precursor can be used. As a specific example, it may be selected from oxygen (O 2 ), ozone (O 3 ), distilled water (H 2 O), hydrogen peroxide (H 2 O 2 ), nitric oxide (NO), nitrous oxide (N 2 O), nitrogen dioxide (NO 2 ), ammonia (NH 3 ), nitrogen (N 2 ), hydrazine (N 2 H 4 ), amine, diamine, carbon monoxide (CO), carbon dioxide (CO 2 ), any one or two or more of C1 to C12 saturated or unsaturated hydrocarbons and hydrogen.

[0094] The transfer gas may be selected from one or two or more of argon, helium, and nitrogen, but is not limited thereto.

[0095] In one embodiment, the deposition conditions can be adjusted according to the structure or properties of the desired thin film. As examples of the deposition conditions, the input flow rate of the aminoalkoxydisilazane compound or the silicon-containing thin film deposition composition containing the same, the input flow rates of the reaction gas and the transfer gas, the pressure, the RF power, and the substrate temperature can be exemplified. As a specific example, the input flow rate of the aminoalkoxydisilazane compound or the silicon-containing thin film deposition composition can be adjusted to 10 cc / min to 1000 cc / min, the transfer gas can be adjusted to 10 cc / min to 1000 cc / min, the flow rate of the reaction gas can be adjusted to 1 cc / min to 1500 cc / min, the pressure can be adjusted to 0.5 torr to 10 torr, the RF power can be adjusted to 50 W to 1000 W, and the substrate temperature can be adjusted to 100 °C to 700 °C, 300 °C to 700 °C, or 400 °C to 700 °C, but not limited thereto.

[0096] The substrate can be a substrate including one or more semiconductor materials selected from 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), polyester, etc., but not limited thereto.

[0097] In addition, in addition to directly forming a thin film on the substrate, a plurality of conductive layers, dielectric layers, or insulating layers, etc. can be formed between the substrate and the silicon-containing thin film.

[0098] According to one embodiment, by using the above-mentioned aminoalkoxydisilazane compound as a precursor, a high-quality silicon-containing thin film can be prepared.

[0099] As an example, as long as the thin film can be prepared within the scope recognizable by those of ordinary skill in the art in the present technical field, the silicon-containing thin film can be used. Specifically, it can be a silicon oxide film (SiO 2) Carbon oxide silicon film (SiOC), silicon nitride film (SiN), silicon oxynitride film (SiON), silicon carbonitride film (SiCN), silicon carbide film (SiC), etc. In addition, various high-quality silicon-containing thin films can be prepared within the scope recognizable by those of ordinary skill in the art and can be used as gate insulating films, dielectric films of capacitors, tunnel insulating films of non-volatile memory elements, etc.

[0100] Hereinafter, the present invention will be described more specifically through the following examples. Before that, the terms or words used in this specification and claims should not be construed as limited to the ordinary or dictionary meanings, and the inventor should, based on the principle of being able to explain his invention in the most preferred manner and appropriately defining the concepts of the terms, interpret them as meanings and concepts conforming to the technical idea of the present invention.

[0101] Therefore, the embodiments described in this specification and the configurations shown in the drawings are only the most preferred embodiments of the present invention and do not represent all the technical ideas of the present invention. Therefore, when applying for the present invention, it should be understood that there are various equivalent and variant examples that can replace them.

[0102] Hereinafter, the synthesis examples are carried out using a glove box or a Schlenk tube in an anhydrous and inert atmosphere. The structure of the aminoalkoxydisilazane compound was analyzed by Nuclear Magnetic Resonance (NMR, 400MHz Ultrashield, Bruker). The thermal stability, volatility and decomposition temperature of the aminoalkoxydisilazane compound were analyzed by Thermogravimetric analysis (TGA, L81-II, LINSEIS).

[0103] Example 1

[0104] Synthesis of ((Dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine

[0105] Step 1: Synthesis of 1-chloro-N-isopropyl-1,1-dimethylsilanamine

[0106]

[0107] Under anhydrous and inert atmosphere, 311.16 g (2.411 mol) of dichlorodimethylsilane ((CH 3 ) 2 SiCl 2 ) and 3319 mL (24.110 mol) of n-pentane (n-C 5 H 12 ) were charged into a flame-dried 10 L flask, and while maintaining the internal temperature at -20 °C, 285.03 g (4.821 mol) of isopropylamine ((CH 3 ) 2 CHNH 2 ) was slowly added. After the addition was completed, the mixture was stirred at room temperature for 3 hours to complete the reaction. Isopropylamine hydrochloride ((CH 3 ) 2 CHNH 2 ·HCl) was removed by filtering the reaction mixture, and after removing the solvent under reduced pressure from the obtained filtrate, under the conditions of 60 °C @ 100 torr, vacuum distillation was carried out to obtain the title compound 1-chloro-N-isopropyl-1,1-dimethylsilanamine ((CH 3 ) 2 CHNHSi(CH 3 ) 2 Cl) (yield 73%).

[0108] 1 H-NMR (C 6 D 6 ): δ 0.25 (s, 6H, Si(CH 3 ) 2 ), 0.92 (d, 6H, (CH(CH 3 ) 2 ), 2.99 (m, 1H, CH).

[0109] Step 2: Synthesis of Lithium dimethylamide

[0110]

[0111] Under anhydrous and inert atmosphere, 917 mL (2.411 mol) of 2.63 M n-butyllithium (n-C 4 H 9 Li) and 786 mL (6.027 mol) of n-hexane (n-C 6 H 14 ) were charged into a flame-dried 3 L flask, and while maintaining the internal temperature at -20 °C, 114.12 g (2.532 mol) of dimethylamine ((CH 3 )2 NH). After the addition is complete, stir for 3 hours at room temperature to complete the reaction. After the reaction is complete, remove the solvent under reduced pressure in a vacuum and dry to obtain the title compound lithium dimethylamide (LiN(CH 3 ) 2 ) in equivalents.

[0112] Step 3: Synthesis of (Dimethylamino)(isopropylamino)dimethylsilane

[0113]

[0114] Under anhydrous and inert atmosphere, charge 15.79 g (0.309 mol) of lithium dimethylamide (LiN(CH 3 ) 2 ) synthesized in Step 2 and 2140 mL (18.569 mol) of n-pentane (n-C 5 H 12 ) into a flame-dried 4 L flask. While maintaining the internal temperature at -40 °C, add 46.95 g (0.309 mol) of 1-chloro-N-isopropyl-1,1-dimethylsilanamine ((CH 3 ) 2 CHNHSi(CH 3 ) 2 Cl) synthesized in Step 1. After the addition is complete, stir for 3 hours at room temperature to complete the reaction. Remove lithium chloride salt (LiCl) by filtering the reaction mixture, and after removing the solvent under reduced pressure from the obtained filtrate, perform vacuum distillation at 25 °C @ 50 torr to obtain 29.6 g (0.185 mol) of the title compound (Dimethylamino)(isopropylamino)dimethylsilane ((CH 3 ) 2 NSi(CH 3 ) 2 NHCH(CH 3 ) 2 )(yield 60%).

[0115] 1 H-NMR(C 6 D 6 ): δ 0.07 (s, 6H, Si(CH 3 ) 2 ), 0.29 (br, 1H, NH), 1.00 (d, 6H, CH(CH 3 ) 2), 2.49 (s, 6H SiN(CH 3 )) 2 ), 2.99 (ds, 1H, CH).

[0116] 13 C NMR (C 6 D 6 )): δ -1.96 (SiCH 3 ), 27.8 (CHCH 3 ), 37.5 (SiNCH 3 ), 42.6 (CH).

[0117] 29 Si-NMR (C 6 D 6 )): δ -7.5.

[0118] Step 4: Synthesis of ((Dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine

[0119]

[0120] Under anhydrous and inert atmosphere, 50 g (0.195 mol) of (Dimethylamino)(isopropylamino)dimethylsilane ((CH 3 )) 2 NSi(CH 3 )) 2 NHCH(CH 3 )) 2 ) synthesized in Step 3 and 1527 mL (11.707 mol) of n-pentane (n-C 6 H 14 ) were charged into a flame-dried 3 L flask. While maintaining the internal temperature at -50 °C, 74 mL (0.195 mol) of 2.63 M n-butyllithium (n-C 4 H 9 Li) was slowly added. After that, the mixture was stirred at room temperature for 3 hours. When the stirring was completed, 29.71 g (0.195 mol) of tetramethyl orthosilicate (Si(OCH 3 )) 4 ) was slowly added to the reaction mixture, and the mixture was stirred at room temperature for 24 hours to complete the reaction. The reaction mixture was filtered to remove lithium methoxide (LiOCH 3), and after removing the solvent under reduced pressure from the obtained filtrate, under the conditions of 48 °C and 0.5 torr, vacuum distillation was carried out to obtain 29 g (0.103 mol) of the title compound ((dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine ((CH 3 ) 2 NSi(CH 3 ) 2 N(CH(CH 3 ) 2 )Si(OCH 3 ) 3 ), as a colorless liquid (yield 53%).

[0121] 1 H-NMR(C 6 D 6 ): δ 0.29 (s, 6H, Si(CH 3 ) 2 ), 1.32 (d, 6H, CH(CH 3 ) 2 ), 2.53 (s, 6H, N(CH 3 ) 2 ), 3.44 (s, 9H, Si(OCH 3 ) 3 ), 3.29 (m, 1H, CH(CH 3 ) 2 ).

[0122] 13 C-NMR(C 6 D 6 ): δ 25.1, 37.70, 45.54, 49.76.

[0123] 29 Si-NMR(C 6 D 6 ): δ -3.96, -62.73.

[0124] Figure 1 shows the thermogravimetric analysis (TGA) results of ((dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine prepared in Example 1. Referring to Figure 1 , it can be seen that the compound of Example 1 has the characteristic of rapid vaporization, and vaporizes more than 99% by weight near about 240 °C, without residual substances caused by thermal decomposition. Thus, it can be known that the compound of Example 1 has excellent thermal stability and excellent volatility.

[0125] As described above, in the present invention, it has been described through specific matters and limited embodiments, but this is only provided for the convenience of more comprehensively understanding the present invention. The present invention is not limited to the above embodiments, and those of ordinary skill in the art to which the present invention pertains can make various modifications and variations based on these descriptions. Therefore, the idea of the present invention should not be limited to the described embodiments, and all contents equivalent to or having equivalent variations to the appended claims fall within the scope of the idea of the present invention.

Claims

1. An aminoalkoxydisilazane compound, wherein The aminoalkoxydisilazane compound is represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, R 1 , R 11 and R 12 Each independently is a C1-C7 alkyl, a C3-C7 cycloalkyl or a C2-C7 alkenyl, or the R 11 and R 12 Connected to form a ring, R 2 and R 3 Each is independently a C1-C7 alkyl, a C3-C7 cycloalkyl or a C1-C7 alkoxy group, R is a C1-C7 alkyl group or a C3-C7 cycloalkyl group, R 4 and R 5 Each is independently a C1-C7 alkyl group, a C3-C7 cycloalkyl group, a C1-C7 alkoxy group or a C3-C7 cycloalkyloxy group.

2. The aminoalkoxydisilazane compound according to claim 1, wherein The R 1 , R 11 and R 12 are each independently C1-C5 alkyl, C3-C7 cycloalkyl or C2-C4 alkenyl, or the R 11 and R 12 C2-C7 alkylene groups are connected to each other to form a ring, R 2 and R 3 Each is independently a C1-C5 alkyl group or a C3-C7 cycloalkyl group, R is a C1-C5 alkyl group or a C3-C7 cycloalkyl group, R 4 and R 5 Each is independently a C1-C5 alkyl group, a C3-C7 cycloalkyl group or a C1-C5 alkoxy group.

3. The aminoalkoxydisilazane compound according to claim 1, wherein The aminoalkoxydisilazane compound is represented by the following Chemical Formula 2 or Chemical Formula 3: [Chemical formula 2] [Chemical formula 3] In the chemical formula 2 and the chemical formula 3, R 1 , R 11 and R 12 Each is independently C1-C4 alkyl, C3-C6 cycloalkyl or C2-C3 alkenyl, R 2 , R 3 , R and R 4a Each is independently a C1-C4 alkyl group or a C3-C6 cycloalkyl group, R 4 and R 5 Each is independently a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C1-C4 alkoxy group, and a is an integer from 0 to 4.

4. The aminoalkoxydisilazane compound according to claim 3, wherein The R 1 , R 11 and R 12 Each is independently a C1-C4 alkyl or a C2-C3 alkenyl, R 2 , R 3 , R and R 4a are each independently C1-C4 alkyl, R 4 and R 5 Each is independently a C1-C4 alkyl group or a C1-C4 alkoxy group, a is an integer from 0 to 3.

5. The aminoalkoxydisilazane compound according to claim 2, wherein The R 1 , R 2 , R 3 , R, R 11 and R 12 are each independently C1-C4 alkyl, R 4 and R 5 Each is independently a C1-C4 alkyl group or a C1-C4 alkoxy group.

6. The aminoalkoxydisilazane compound according to claim 1, wherein The aminoalkoxydisilazane compound is selected from the following structures:

7. A composition for deposition of a silicon-containing thin film, wherein: The method comprises an aminoalkoxydisilazane compound selected from the group consisting of the aminoalkoxydisilazane compounds according to any one of claims 1 to 6.

8. A method for preparing a silicon-containing film, wherein: The method comprises the steps of depositing a silicon-containing thin film using an aminoalkoxydisilazane compound represented by the following Chemical Formula 1 or a composition for depositing a silicon-containing thin film comprising the aminoalkoxydisilazane compound, [Chemical formula 1] In the chemical formula 1, R, R 1 To R 5 , R 11 and R 12 Same as the definition in claim 1.

9. The method for preparing a silicon-containing thin film according to claim 8, wherein: The preparation method is carried out by atomic layer deposition, vapor deposition, metal organic chemical vapor deposition, low pressure vapor deposition, plasma enhanced vapor deposition or plasma enhanced atomic layer deposition.

10. The method for preparing a silicon-containing thin film according to claim 8, wherein: The silicon-containing thin film is a silicon oxide film, a silicon oxycarbide film, a silicon nitride film, a silicon oxynitride film, a silicon carbonitride film, or a silicon carbide film.

Images