Aminoalkoxydisilazane compound, composition for depositing silicon-containing thin film comprising the same, and method of manufacturing silicon-containing thin film using the same
Patent Information
- Application Number
- TW113147310
- Authority / Receiving Office
- TW · TW
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2024-10-29
- Filing Date
- 2024-12-05
- Publication Date
- 2026-10-11
- Estimated Expiration
- 2044-12-04
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Figure TWG2TB001915257_001 
Figure TWG2TB001915257_002
Abstract
Description
Technical Field
[0001] The present invention relates to an aminoalkoxydisilazane compound, a composition for depositing a silicon-containing film comprising the aminoalkoxydisilazane compound, and a method for preparing a silicon-containing film using the aminoalkoxydisilazane compound. Prior Art
[0002] Silicon-containing thin films are essential materials in semiconductor manufacturing and are used in various forms such as silicon film, silicon oxide film, silicon nitride film, silicon carbonitride film, and silicon oxynitride film. These films play an essential role in advanced electronic devices such as memory, logic chips, flat panel displays (TFTs, thin film transistors) and solar cells, and are used as semiconductor substrates, diffusion masks, anti-oxidation 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 continued to increase.
[0003] In order to deposit silicon-containing thin films, various silicon precursors (such as aminosilane and alkoxysilane) are being developed, including existing silicon precursors (such as silane, disilane and silane halide), and representative processes include chemical vapor deposition (CVD) and atomic layer deposition (ALD). In particular, ALD is very effective in forming ultra-fine films with uniform thickness, so it is an essential process for realizing fine patterns in the latest semiconductor devices. In addition, deposition technology using plasma (PECVD (plasma-enhanced chemical vapor deposition) and PEALD (plasma-enhanced atomic layer deposition)) can deposit thin films under low temperature conditions, and thus has become an important technology for preparing next-generation semiconductors and display devices.
[0004] In recent years, the miniaturization and high integration of ultra-fine semiconductor devices are progressing rapidly, and the requirements for silicon precursors have become more stringent. Precursors should be stable and highly volatile at room temperature, have no non-volatile by-products during the film deposition process, have significant thermal stability and reactivity at high temperatures, and be easy to handle, transport and store. In order to deposit high-quality films, precursors with these characteristics are necessary.
[0005] Due to the development of ultra-highly integrated semiconductor devices, existing precursors have limitations in forming uniform thin films under low temperature conditions, and also have problems with reduced production capacity and physical and electrical properties. Therefore, it is necessary to develop a new silicon precursor that can be deposited quickly and uniformly at low temperatures while having excellent physical properties.
[0006] [Prior Technical Literature] [Patent Document] (Patent Document 1) KR 10-2023-0151303 A (November 1, 2023). Summary of the invention
[0007] Problem that the invention aims to solve
[0008] One embodiment of the present invention is to provide an aminoalkoxy disilazane compound and a composition comprising the same for depositing a silicon-containing film. The aminoalkoxy disilazane compound can be used as a precursor for depositing a silicon-containing film.
[0009] Another embodiment of the present invention provides a method for preparing a silicon-containing thin film by using the aminoalkoxydisilazane compound or a composition for depositing a silicon-containing thin film comprising the aminoalkoxydisilazane compound.
[0010] Means used to solve problems
[0011] In one general scheme, an aminoalkoxydisilazane compound represented by the following Chemical Formula 1 is provided: [Chemical formula 1] , In chemical formula 1, R1, R11 and R12 are each independently C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkenyl, or R11 and R12 may be connected to each other to form a ring, R2 and R3 are each independently C1-C7 alkyl, C3-C7 cycloalkyl or C1-C7 alkoxy, R is a C1-C7 alkyl group or a C3-C7 cycloalkyl group, and R4 and R5 are each independently C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 alkoxy or C3-C7 cycloalkyloxy.
[0012] In another general embodiment, a composition for depositing a silicon-containing film comprising an aminoalkoxydisilazane compound according to an exemplary embodiment of the present invention is provided.
[0013] In another general embodiment, a method for preparing a silicon-containing film is provided, which uses an aminoalkoxydisilazane compound according to an exemplary embodiment of the present invention or a composition for depositing a silicon-containing film comprising the aminoalkoxydisilazane compound.
[0014] Effects of the Invention
[0015] The aminoalkoxydisilazane compound of the present invention has excellent volatility and thermal stability, exists in a liquid state at normal temperature and pressure, is easy to store and handle, and has high reactivity. Therefore, it can be used as a precursor for depositing a silicon-containing film, and can form a high-purity and high-quality silicon-containing film.
[0016] The aminoalkoxydisilazane compound of the present invention is used as a precursor for depositing a thin film, and a high-quality silicon-containing thin film with high silicon content, thermal stability and remarkable durability can be prepared.
[0017] In addition, the silicon-containing 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. Simple diagram description
[0018] FIG. 1 shows the thermogravimetric analysis (TGA) results of ((dimethylamino)dimethylsilyl) (trimethoxysilyl) (isopropyl)amine prepared in Example 1. Implementation
[0019] In this specification, unless otherwise defined, all technical terms and scientific terms have the same meanings as those commonly understood by those skilled in the art in the technical field to which the present invention belongs. The terms used in this specification are only used to effectively describe specific embodiments and are not used to limit the present invention.
[0020] Unless the context specifically indicates otherwise, expressions of a single number used in this specification may also include expressions of a plural number.
[0021] Throughout this specification, unless otherwise specifically described, when reference is made to “including”, “configured with”, “containing” or “having” a certain constituent element, it does not mean to exclude other constituent elements, but rather may also include other constituent elements, and does not exclude additional unlisted elements, materials or processes.
[0022] The numerical range used in this specification includes the lower limit and the upper limit and all values within the 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 range defined in different forms. As an example, when the content of a composition is limited to 10% to 80% or 20% to 50%, the numerical range of 10% to 50% or 50% to 80% should also be interpreted as the content recorded in this specification. Unless otherwise specifically defined in this specification, values outside the numerical range that may appear due to experimental errors or rounding of values are also included in the defined numerical range.
[0023] 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.
[0024] Unless otherwise specifically mentioned, the units used in this specification are based on weight. As an example, the unit of "%" or "ratio" refers to "weight %" or "weight ratio", and unless otherwise defined, "weight %" refers to the weight % of any component in the entire composition.
[0025] The term "CA-CB" in this specification means "the number of carbon atoms is A or more and B or less", and the term "A to B" means "A or more and B or less".
[0026] The term "alkyl" in this specification refers to a monovalent organic group derived from a straight-chain or branched saturated hydrocarbon and has 1 to 7, 1 to 5, 1 to 4 or 1 to 3 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, isobutyl, pentyl, etc.
[0027] The term "cycloalkyl" in this specification refers to a monovalent saturated carbocyclic group formed by one or more rings. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.
[0028] The term "alkenyl" in this specification refers to a straight or branched hydrocarbon group containing 2 to 7 carbon atoms and one or more carbon-carbon double bonds. Specifically, the alkenyl group is a lower alkenyl group having 2 to 7, 2 to 5, 2 to 4 or 2 to 3 carbon atoms. Examples of alkenyl groups may include vinyl, propenyl, isopropenyl, allyl, butenyl, 4-methylbutenyl, etc. The alkenyl group may include groups having cis and trans orientations, or alternatively having E and Z orientations.
[0029] In this specification, "normal temperature" may refer to a temperature without artificial temperature control. For example, the normal temperature may be 20°C to 40°C, or 20°C to 30°C, or 23°C to 26°C.
[0030] The present invention is described in detail below. However, this is merely exemplary, and the present invention is not limited to the specific embodiments described exemplarily.
[0031] An exemplary embodiment of the present invention provides an aminoalkoxydisilazane compound, which is used as a precursor for preparing a high-quality silicon-containing film. Specifically, the aminoalkoxydisilazane compound according to an exemplary embodiment is represented by the following chemical formula 1: [Chemical formula 1] , In chemical formula 1, R1, R11 and R12 are each independently C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkenyl, Alternatively, the R 11 and R 12 may be connected to each other to form a ring, R2 and R3 are each independently C1-C7 alkyl, C3-C7 cycloalkyl or C1-C7 alkoxy, R is a C1-C7 alkyl group or a C3-C7 cycloalkyl group, and R4 and R5 are each independently C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 alkoxy or C3-C7 cycloalkyloxy.
[0032] According to an exemplary embodiment, the aminoalkoxydisilazane 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 another Si. According to an exemplary embodiment, the aminoalkoxydisilazane compound can also have a lower activation energy and excellent thermal stability according to the above structural characteristics and the asymmetric structure of the silicon moiety (moiety) existing on both sides with the central N of the disilazane skeleton as the center, thereby significantly improving the reactivity and not generating non-volatile by-products, so that it is easy to form a high-quality silicon-containing film at a high deposition rate. According to an exemplary embodiment of the present invention, the aminoalkoxydisilazane compound exists in a liquid state at room temperature and a pressure condition that can be handled, so it is easy to handle.
[0033] In an exemplary embodiment, in Chemical Formula 1, R1, R11 and R12 may each independently be a C1-C5 alkyl group, a C3-C7 cycloalkyl group or a C2-C4 alkenyl group, or R11 and R12 may be connected to each other through a C2-C7 alkylene group to form a ring, R2 and R3 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, and R4 and R5 may each independently be a C1-C5 alkyl group, a C3-C7 cycloalkyl group or a C1-C5 alkoxy group.
[0034] In one specific example, in Chemical Formula 1, R1, R11 and R12 may each independently be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C2-C3 alkenyl group, R2, R3 and R4 may each independently be a C1-C4 alkyl group or a C3-C6 cycloalkyl group, R4 may be a C1-C4 alkoxy group or a C3-C6 cycloalkyloxy group, and R5 may be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C1-C4 alkoxy group.
[0035] In a specific example, in Chemical Formula 1, R1 can be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C2-C3 alkenyl group, R11 and R12 can be connected to each other through a C2-C6 alkylene group to form a ring, R2, R3 and R4 can each independently be a C1-C4 alkyl group or a C3-C6 cycloalkyl group, and R4 and R5 can each independently be a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C1-C4 alkoxy group.
[0036] In one specific example, in Chemical Formula 1, R1, R11 and R12 may each independently be a C1-C4 alkyl group or a C2-C3 alkenyl group, R2, R3 and R4 may each independently be a C1-C4 alkyl group, and R4 and R5 may each independently be a C1-C4 alkyl group or a C1-C4 alkoxy group.
[0037] In one embodiment, in Chemical Formula 1, R1, R2, R3, R, R11 and R12 may each independently be a C1-C4 alkyl group, and R4 and R5 may each independently be a C1-C4 alkyl group or a C1-C4 alkoxy group.
[0038] In an exemplary embodiment, the aminoalkoxydisilazane compound can be represented by the following Chemical Formula 2 or Chemical Formula 3: [Chemical formula 2] , [Chemical formula 3] , In Chemical Formula 2 and Chemical Formula 3, R1, R11 and R12 are each independently C1-C4 alkyl, C3-C6 cycloalkyl or C2-C3 alkenyl, R2, R3, R4a are each independently C1-C4 alkyl or C3-C6 cycloalkyl, R4 and R5 are each independently C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 alkoxy, and a is an integer of 0-4.
[0039] In one specific example, R1, R11 and R12 can each independently be a C1-C4 alkyl group or a C2-C3 alkenyl group, R2, R3, R4a and R4a can each independently be a C1-C4 alkyl group, R4 and R5 can each independently be a C1-C4 alkyl group or a C1-C4 alkoxy group, and a can be an integer from 0 to 3.
[0040] In an exemplary embodiment, the aminoalkoxydisilazane compound can be represented by the following chemical formula 4: [Chemical formula 4] , In chemical formula 4, R1 is C1-C4 alkyl or C2-C3 alkenyl, R 21 is a C1-C4 alkyl group, R 22 is a C1-C4 alkyl group or a C1-C4 alkoxy group, R is a C1-C4 alkyl group, and R23 is a C1-C4 alkyl group or a C2-C3 alkenyl group.
[0041] As an example, the R 1 may be a C1-C3 alkyl group or a C2-C3 alkenyl group, and as a specific example, may be a methyl group, an ethyl group, an isopropyl group, a vinyl group, an isopropenyl group or an allyl group.
[0042] As an example, the R 21 may be a C1-C3 alkyl group, and as a specific example, may be a methyl group or an ethyl group.
[0043] As an example, the R 22 may be a C1-C3 alkyl group or a C1-C3 alkoxy group, or may be a C1-C3 alkoxy group, and as a specific example, may be a methyl group, an ethyl group, a methoxy group or an ethoxy group.
[0044] As an example, the R may be a C1-C3 alkyl group, and as a specific example, may be a methyl group or an ethyl group.
[0045] As an example, the R 23 may be a C1-C3 alkyl group or a C2-C3 alkenyl group, and as a specific example, may be an ethyl group, an isopropyl group, a vinyl group, an isopropenyl group or an allyl group.
[0046] In an exemplary embodiment, the aminoalkoxydisilazane compound can be selected from the following compounds, but is not limited thereto: .
[0047] The aminoalkoxydisilazane compound can be prepared by any possible method within the scope understandable to those skilled in the art.
[0048] Another exemplary embodiment of the present invention provides a composition for depositing a silicon-containing film, wherein the composition comprises an aminoalkoxydisilazane compound according to an exemplary embodiment.
[0049] In an exemplary embodiment, the composition for depositing a silicon-containing film comprises an aminoalkoxydisilazane compound having high volatility and excellent thermal stability as a precursor for depositing the film, and the content thereof can be within a range understandable to those skilled in the art, taking into account the film forming conditions or the thickness and characteristics of the film.
[0050] Another embodiment of the present invention provides a method for preparing a silicon-containing film, the method comprising the step of depositing a silicon-containing film using an aminoalkoxydisilazane compound represented by Chemical Formula 1 or a composition for depositing a silicon-containing film comprising the aminoalkoxydisilazane compound.
[0051] In an exemplary embodiment, in the method for preparing a silicon-containing film, by using the aminoalkoxydisilazane compound as a precursor, a high-quality silicon-containing film can be prepared at a high deposition rate under various conditions.
[0052] In an exemplary embodiment, the method for preparing the silicon-containing thin film can be used without limitation as long as it is a possible method within the scope understandable to those skilled in the art, for example, it can be performed 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).
[0053] In an exemplary embodiment, the aminoalkoxydisilazane compound and the reaction gas may be supplied continuously or discontinuously, and the discontinuous supply may include a pulse form.
[0054] As an example, the method for preparing a silicon-containing film may include: step a), maintaining the temperature of a substrate installed in a chamber at above 100° C.; step b), adsorbing an aminoalkoxydisilazane compound according to an exemplary embodiment or a composition for depositing a silicon-containing film including the aminoalkoxydisilazane compound onto the substrate; and step c), injecting a reaction gas into the substrate on which the aminoalkoxydisilazane compound or the composition for depositing a silicon-containing film including the aminoalkoxydisilazane compound is adsorbed to deposit the silicon-containing film.
[0055] The method for preparing the silicon-containing film may further include: a step of removing unreacted reactants by purging.
[0056] Specifically, the method for preparing a silicon-containing 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 aminoalkoxydisilazane compound according to an exemplary embodiment or a composition for depositing a silicon-containing film including the aminoalkoxydisilazane compound onto the substrate; step b-2), purging the residual aminoalkoxydisilazane compound or the residual composition for depositing a film and by-products; step c-1), injecting a reaction gas into the substrate on which the aminoalkoxydisilazane compound or the composition for depositing a film including the aminoalkoxydisilazane compound is adsorbed to form a silicon-containing film; and step c-2), purging the residual reaction gas and by-products.
[0057] As an example, when the method for preparing a silicon-containing film is performed by plasma enhanced atomic layer deposition (PEALD) or plasma enhanced chemical vapor deposition (PECVD), after step a), it may further include: a step of generating plasma.
[0058] As an example, in the method for preparing a silicon-containing thin film, in the step b), the aminoalkoxydisilazane compound or the composition for depositing a silicon-containing thin film comprising the aminoalkoxydisilazane compound may be injected together with a carrier gas.
[0059] Taking into account the type of silicon-containing film to be prepared, the reaction gas can be used as long as it is a gas commonly used with the precursor, and as a specific example, it can be any 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 to C12 saturated or unsaturated hydrocarbons and hydrogen.
[0060] The transmission gas may be one or more selected from argon, helium and nitrogen, but is not limited thereto.
[0061] In an exemplary embodiment, the deposition conditions can be adjusted according to the structure or characteristics of the desired thin film, and as an example of the deposition conditions, the input flow rate of the aminoalkoxydisilazane compound or the composition for depositing a silicon-containing thin film including the aminoalkoxydisilazane compound, the input flow rate of the reaction gas, the input flow rate of the transport gas, the pressure, the RF (radio frequency) power, and the substrate temperature can be illustrated. As a specific example, the input flow rate of the aminoalkoxydisilazane compound or the composition for depositing a silicon-containing thin film can be adjusted to 10 cc (cubic centimeters) / minute to 1000 cc / minute, the transport gas can be adjusted to 10 cc / minute to 1000 cc / minute, the flow rate of the reaction gas can be adjusted to 1 cc / minute to 1500 cc / minute, the pressure can be adjusted to 0.5 torr to 10 torr, the RF power can be adjusted to 50 watts (W) to 1000 watts, 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 are not limited thereto.
[0062] The substrate may 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; 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 is not limited thereto.
[0063] In addition, in addition to directly forming the silicon-containing film on the substrate, a plurality of conductive layers, dielectric layers or insulating layers may be formed between the substrate and the silicon-containing film.
[0064] According to an exemplary embodiment, high-quality silicon-containing thin films can be prepared by using the aminoalkoxydisilazane compound as a precursor.
[0065] As an example, the silicon-containing film may be any film as long as it is a film that can be prepared within the scope understood by those skilled in the art, and 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), etc. In addition, a variety of high-quality thin films containing silicon can be prepared within the scope understood by those skilled in the art, and can be used as gate insulating films, dielectric films of capacitors, tunnel insulating films of non-volatile memory devices, etc.
[0066] The present invention is described in more detail below through the following examples. Prior to this, the terms or words used in this specification and the scope of the patent application should not be interpreted as limited to the usual or dictionary meanings, and should be interpreted as the meanings and concepts that are consistent with the technical ideas of the present invention based on the principle that the inventor appropriately defines the concepts of the terms based on the best way to explain his invention.
[0067] Therefore, the embodiments described in this specification and the structures shown in the drawings are only the best implementation modes 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 also many equivalents and modified examples that can replace them.
[0068] The following synthetic examples were performed in anhydrous and inert atmosphere using a glove box or Schlenk tube. The structure of the aminoalkoxydisilazane compound was analyzed by nuclear magnetic resonance (NMR, 400MHz Ultrashield, Buruker). The thermal stability, volatility and decomposition temperature of the aminoalkoxydisilazane compound were analyzed by thermogravimetric analysis (TGA, L81-II, LINSEIS).
[0069] Example 1
[0070] Synthesis of ((dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine
[0071] Step 1: Synthesis of 1-chloro-N-isopropyl-1,1-dimethylsilanamine
[0072] Under anhydrous and inert atmosphere, 311.16 g (2.411 mol) of dichlorodimethylsilane ((CH 3) 2SiCl 2) and 3319 ml (24.110 mol) of n-pentane (nC 5H 12) were placed in a flame-dried 10-liter flask, and 285.03 g (4.821 mol) of isopropylamine ((CH 3) 2CHNH 2) was slowly added while maintaining the internal temperature at -20°C. After the addition was completed, the mixture was stirred at room temperature for 3 hours to complete the reaction. The reaction mixture was filtered to remove isopropylamine hydrochloride ((CH 3) 2CHNH 2·HCl), and the solvent was removed from the obtained filtrate under reduced pressure. Then, the target compound 1-chloro-N-isopropyl-1,1-dimethylsilaneamine ((CH 3) 2CHNHSi(CH 3) 2Cl) was obtained by reduced pressure distillation at 60°C@100 Torr (yield: 73%). 1H-NMR (C 6D 6): δ 0.25(s, 6H, Si(CH 3) 2), 0.92 (d, 6H, (CH(CH 3) 2), 2.99(m, 1H, CH)
[0073] Step 2: Synthesis of lithium dimethylamide
[0074] Under anhydrous and inert atmosphere, 917 ml (2.411 mol) of 2.63 M n-butyl lithium (nC 4H 9Li) and 786 ml (6.027 mol) of n-hexane (nC 6H 14) were placed in a flame-dried 3-liter flask, and 114.12 g (2.532 mol) of dimethylamine ((CH 3) 2NH) was slowly added while maintaining the internal temperature at -20°C. After the addition was completed, the mixture was stirred at room temperature for 3 hours to complete the reaction. After the reaction was completed, the solvent was removed under vacuum and dried to obtain the target compound, lithium dimethylamide (LiN(CH 3) 2), in equivalents.
[0075] Step 3: Synthesis of (dimethylamino)(isopropylamino)dimethylsilane
[0076] Under anhydrous and inert atmosphere, 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 (nC 5H 12) were placed in a flame-dried 4-liter flask, and 46.95 g (0.309 mol) of 1-chloro-N-isopropyl-1,1-dimethylsilaneamine ((CH 3) 2CHNHSi(CH 3) 2Cl) synthesized in step 1 was added while maintaining the internal temperature at -40°C. After the addition was completed, the mixture was stirred at room temperature for 3 hours to complete the reaction. The reaction mixture was filtered to remove lithium chloride (LiCl), and the solvent was removed from the obtained filtrate under reduced pressure, followed by vacuum distillation at 25°C @ 50 Torr to obtain 29.6 g (0.185 mol) of the target compound (dimethylamino) (isopropylamino) dimethylsilane ((CH 3) 2NSi(CH 3) 2NHCH(CH 3) 2) (yield 60%). 1H-NMR (C 6D 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) 13C NMR (C 6D 6): δ -1.96 (SiCH 3), 27.8 (CHCH 3), 37.5(SiNCH 3), 42.6(CH) 29Si-NMR (C 6D 6): δ -7.5
[0077] Step 4: Synthesis of ((dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine
[0078] Under anhydrous and inert atmosphere, 50 g (0.195 mol) of (dimethylamino)(isopropylamino)dimethylsilane ((CH 3) 2NSi(CH 3) 2NHCH(CH 3) 2) synthesized in step 3 and 1527 ml (11.707 mol) of n-hexane (nC 6H 14) were placed in a flame-dried 3-liter flask, and 74 ml (0.195 mol) of 2.63 M n-butyllithium (nC 4H 9Li) was slowly added while maintaining the internal temperature at -50°C, and stirred at room temperature for 3 hours. After 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 stirred at room temperature for 24 hours to complete the reaction. The reaction mixture was filtered to remove lithium methoxide (LiOCH 3), and the solvent was removed from the obtained filtrate under reduced pressure. Then, distillation was performed under reduced pressure at 48°C@0.5 torr to obtain 29 g (0.103 mol) of the target compound ((dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine ((CH 3) 2NSi(CH 3) 2N(CH(CH 3) 2)Si(OCH 3) 3), which was a colorless liquid (yield 53%). 1H-NMR (C 6D 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) 13C-NMR (C 6D 6): δ 25.1, 37.70, 45.54, 49.76 29Si-NMR (C 6D 6): δ -3.96, -62.73
[0079] FIG1 shows the thermogravimetric analysis (TGA) results of ((dimethylamino)dimethylsilyl)(trimethoxysilyl)(isopropyl)amine prepared in Example 1. Referring to FIG1 , it can be seen that the compound of Example 1 has the characteristic of rapid vaporization, and vaporizes more than 99% by weight at about 240° C., and there is no residual substance caused by thermal decomposition. It can be seen that the compound of Example 1 has excellent thermal stability and excellent volatility.
[0080] The above embodiments are only used to illustrate the principle and efficacy of the present invention and to describe the technical features of the present invention, and are not used to limit the scope of protection of the present invention. Any changes or arrangements that can be easily completed by anyone familiar with the present technology without violating the technical principle and spirit of the present invention are within the scope claimed by the present invention. Therefore, the scope of protection of the present invention is as listed in the attached patent application scope.
Claims
1. An aminoalkoxydisilazane compound represented by the following chemical formula 1, [Chemical Formula 1], wherein R1, R11 and R12 are each independently C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkenyl, or R11 and R12 are interconnected to form a ring, R2 and R3 are each independently C1-C7 alkyl, C3-C7 cycloalkyl or C1-C7 alkoxy, R is C1-C7 alkyl or C3-C7 cycloalkyl, and R4 and R5 are each independently C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 alkoxy or C3-C7 cycloalkyloxy.
2. The aminoalkoxydiasilazane compound as claimed in claim 1, wherein R1, R11 and R12 are each independently C1-C5 alkyl, C3-C7 cycloalkyl or C2-C4 alkenyl, or R11 and R12 are interconnected to form a ring through C2-C7 alkenyl groups, R2 and R3 are each independently C1-C5 alkyl or C3-C7 cycloalkyl, R is C1-C5 alkyl or C3-C7 cycloalkyl, and R4 and R5 are each independently C1-C5 alkyl, C3-C7 cycloalkyl or C1-C5 alkoxy.
3. The aminoalkoxydisilazane compound as claimed in claim 1, wherein, The aminoalkoxybissilazane compound is represented by the following chemical formula 2 or chemical formula 3: [chemical formula 2], [chemical formula 3], in chemical formula 2 and chemical formula 3, R1, R11 and R12 are each independently C1-C4 alkyl, C3-C6 cycloalkyl or C2-C3 alkenyl, R2, R3, R and R4a are each independently C1-C4 alkyl or C3-C6 cycloalkyl, R4 and R5 are each independently C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 alkoxy, and a is an integer from 0 to 4.
4. The aminoalkoxydisilazane compound as claimed in claim 3, wherein, R1, R11 and R12 are each independently C1-C4 alkyl or C2-C3 alkenyl, R2, R3, R and R4a are each independently C1-C4 alkyl, R4 and R5 are each independently C1-C4 alkyl or C1-C4 alkoxy, and a is an integer from 0 to 3.
5. The aminoalkoxydisilazane compound as claimed in claim 2, wherein, R1, R2, R3, R, R11 and R12 are each independently C1-C4 alkyl, and R4 and R5 are each independently C1-C4 alkyl or C1-C4 alkoxy.
6. The aminoalkoxydisilazane compound as claimed in claim 1, wherein, The aminoalkoxydiasilazane compound is selected from the following structures: .
7. A composition for depositing silicon-containing thin films, comprising an aminoalkoxydisilazane compound as described in any one of claims 1 to 6.
8. A method for preparing a silicon-containing thin film, comprising the step of depositing a silicon-containing thin film using an aminoalkoxydisilazane compound represented by the following chemical formula 1 or a composition comprising the following for depositing a silicon-containing thin film: [Chemical Formula 1], wherein R, R1 to R5, R11 and R12 are as defined in claim 1.
9. The method for preparing a silicon-containing thin film as described in claim 8, wherein, This method is performed using atomic layer deposition (ALD) or chemical vapor deposition (CVD).
10. The method for preparing a silicon-containing thin film as described in claim 8, wherein, The silicon-containing thin film is a silicon oxide (SiO2) film, a silicon oxide (SiOC) film, a silicon nitride (SiN) film, a silicon oxynitride (SiON) film, a silicon carbonitride (SiCN) film, or a silicon carbide (SiC) film.
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