Asymmetric silicon precursor compounds, methods for preparing the same, and methods for preparing silicon-containing thin films - Patents.com

Asymmetric silicon precursor compounds with alkoxide structures address the challenges of step coverage and impurity inclusion in thin films, enabling high-quality silicon-containing films for advanced semiconductors.

JP2025533587APending Publication Date: 2025-10-07MERCK PATENT GMBH
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Patent Information

Application Number
JP2025517926
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Priority Date
2022-09-27
Filing Date
2023-09-26
Publication Date
2025-10-07

AI Technical Summary

Technical Problem

Conventional silicon precursor compounds struggle to achieve good step coverage and thickness control for highly integrated semiconductor devices, and often include impurities in silicon-containing thin films.

Method used

Development of asymmetric silicon precursor compounds with alkoxide structures, prepared through specific reaction schemes, allowing for the formation of high-quality silicon-containing thin films using methods like CVD, PECVD, and ALD.

Benefits of technology

The asymmetric silicon precursor compounds enable high deposition rates and excellent quality silicon-containing thin films, particularly suitable for advanced semiconductor applications.

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Abstract

The present invention relates to an alkoxide-containing asymmetric silicon precursor compound capable of preparing high-quality silicon-containing thin films, a method for preparing the same, and a method for preparing silicon-containing thin films using the alkoxide-containing asymmetric silicon precursor compound.
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Description

[Technical Field]

[0001] The present invention relates to alkoxide-containing silicon precursor compounds of asymmetric structure, methods for preparing the same, and methods for preparing silicon-containing thin films using the silicon precursor compounds. [Background technology]

[0002] Silicon-containing thin films are used as semiconductor substrates, diffusion masks, oxidation inhibitors, and dielectric films in semiconductor technologies such as microelectronic devices such as RAM (memory and logic chips), flat panel displays containing thin film transistors (TFTs), and solar energy.

[0003] In particular, with the increasing integration of semiconductor devices, silicon-containing thin films with various properties are required. As the aspect ratio increases with the increasing integration of semiconductor devices, there has been a problem that the deposition of silicon-containing thin films using conventional precursors cannot satisfy the required performance.

[0004] Thin film deposition using conventional precursors is difficult to achieve good step coverage and thickness control for highly integrated semiconductor devices, and impurity inclusion in the thin films is also a problem.

[0005] Therefore, there is a need to develop a variety of silicon precursor compounds with different physical and chemical properties as silicon precursors necessary for forming high-quality silicon-containing films. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Korean Patent Publication No. 2011-0017404 Summary of the Invention [Problem to be solved by the invention]

[0007] Disclosure of the Invention

[0008] The object of the present invention is to provide a novel silicon precursor compound with an asymmetric structure containing alkoxide, which can be used to prepare silicon-containing thin films of excellent quality, and a method for preparing the same.

[0009] Yet another object is to provide a method for preparing silicon-containing thin films using novel silicon precursor compounds of asymmetric structure containing alkoxides. [Means for solving the problem]

[0010] To achieve the above object, the present invention provides a silicon precursor compound represented by the following formula 1:

[0011] [ka]

[0012] In Formula 1, n is 1 or 2, and R 1 is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 R 2 and R 3 are hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 R 4 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, and R 5 is methyl (Me), ethyl (Et), isopropyl ( isoPr), SiMe3, SiHMe2, SiH2Me, SiH3, SiHClMe, SiHCl2, SiMe2CH2CH3, SiMe2CH=CH2, and SiHMeCH=CH2, and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso In the silicon precursor compound of the present invention, R 4 and R 5 may be different from each other, and preferably, R 4 and R 5 are different from each other.

[0013] The silicon precursor compound of the present invention is preferably selected from the group consisting of the following compounds (1) to (56).

[0014] [ka]

[0015] [ka]

[0016] [ka]

[0017] [ka]

[0018] To achieve another object, a method for preparing the silicon precursor compound of the present invention may include reacting an alkoxide compound with a secondary amine, or reacting an alkoxide compound with an alkylaminosilane to prepare the silicon precursor compound represented by Formula 1.

[0019] The alkoxide compound is preferably a compound represented by the following formula 4:

[0020] [ka]

[0021] In Formula 4, n is 1 or 2, and R 1 is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 R 2 and R 3 are hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso Pr).

[0022] In the method for preparing a silicon precursor compound, a silicon precursor compound represented by the following formula 8 can be prepared by reacting an alkoxide compound with a secondary amine.

[0023] [ka]

[0024] In Equation 8, R 1 is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8R 3 are hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 R 4 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, and R 5 is methyl (Me), ethyl (Et), isopropyl ( iso Pr), SiMe3, SiHMe2, SiH2Me, SiH3, SiHClMe, SiHCl2, SiMe2CH2CH3, SiMe2CH=CH2, and SiHMeCH=CH2, and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso Pr).

[0025] In the method for preparing a silicon precursor compound, a silicon precursor compound represented by the following formula 15 or 18 can be prepared by reacting an alkoxide compound with an alkylaminosilane.

[0026] [ka]

[0027] [ka]

[0028] In Formula 15 or Formula 18, R 1 is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR7 R 8 R 2 , R 2 ', R 3 , and R 3 ' represents hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 R 0 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, and R 9 , R 10 , and R 11 are each one selected from hydrogen (H), chlorine (Cl), a methyl group (Me), an ethyl group (CHCH), and a vinyl group (CH=CH), and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso Pr).

[0029] The silicon precursor compound of formula 1 prepared by the method for preparing a silicon precursor compound of the present invention is at least one selected from compounds (1) to (56).

[0030] To achieve another object, the method for preparing a silicon-containing thin film according to the present invention can use a silicon precursor compound represented by Formula 1 to form a silicon-containing thin film.

[0031] In the method for preparing a silicon-containing thin film according to the present invention, the silicon precursor compound is at least one selected from the compounds (1) to (56).

[0032] In the method for preparing a silicon-containing thin film according to the present invention, the silicon-containing thin film can be deposited by chemical vapor deposition (CVD), plasma-enhanced chemical vapor deposition (PECVD), or atomic layer deposition (ALD). [Effects of the Invention]

[0033] The silicon precursor compound of the present invention exhibits sufficient volatility to be applied to atomic layer deposition (ALD), plasma enhanced chemical vapor deposition (PECVD), and chemical vapor deposition (CVD) for preparing silicon-containing thin films. In particular, it can be deposited at high deposition rates even at high temperatures, so that silicon-containing thin films of excellent quality can be prepared.

[0034] However, the effects of the present invention are not limited to these. [Brief explanation of the drawings]

[0035] [Figure 1] 1 shows the hydrogen nuclear magnetic resonance ( 1 H-NMR) spectrum of the silicon precursor compound prepared according to Example 1 of the present invention. [Figure 2] 1 shows the hydrogen nuclear magnetic resonance ( 1 H-NMR) spectrum of the silicon precursor compound prepared according to Example 2 of the present invention. [Figure 3] 1 shows the hydrogen nuclear magnetic resonance ( 1 H-NMR) spectrum of the silicon precursor compound prepared according to Example 3 of the present invention. [Figure 4] 1 shows the hydrogen nuclear magnetic resonance ( 1 H-NMR) spectrum of the silicon precursor compound prepared according to Example 4 of the present invention. [Figure 5] 1 shows the hydrogen nuclear magnetic resonance ( 1 H-NMR) spectrum of the silicon precursor compound prepared according to Example 5 of the present invention. [Figure 6] 1 shows the hydrogen nuclear magnetic resonance ( 1 H-NMR) spectrum of the silicon precursor compound prepared according to Example 6 of the present invention. [Figure 7]1 is a graph showing the results of thermogravimetric analysis (TGA) of silicon precursor compounds prepared according to examples of the present invention. [Figure 8] 1 is a graph showing the results of measuring the vapor pressure of silicon precursor compounds prepared according to Examples 2, 3, 5, and 6 of the present invention. [Figure 9] 1 is a graph showing the sequence of pulses in a silicon oxide thin film deposition process. [Figure 10] 1 shows the results of AES (Auger Electron Spectroscopy) analysis of the composition of a silicon oxide thin film deposited according to the present invention. [Figure 11] 1 is an image of a silicon oxide thin film deposited according to the present invention, observed using a transmission electron microscope (TEM). [Figure 12] 1 is an image of a silicon oxide thin film deposited according to the present invention, observed using a transmission electron microscope (TEM). [Figure 13] 1 is an image of a silicon oxide thin film deposited according to the present invention, observed using a transmission electron microscope (TEM). DETAILED DESCRIPTION OF THE INVENTION

[0036] The silicon precursor compounds according to the present invention and methods for preparing the same are described in detail below.

[0037] As used herein, the term "about" is intended to encompass ±5% of the defined number.

[0038] The alkoxide-containing silicon precursor compound of asymmetric structure according to the present invention can be represented by the following formula 1:

[0039] [ka]

[0040] In Formula 1, n is 1 or 2, and R 1is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 R 2 and R 3 are hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 R 4 is a linear or branched, saturated or unsaturated hydrocarbon group (e.g., having 1 to 6 carbon atoms) or an isomer thereof, and R 5 is methyl (Me), ethyl (Et), isopropyl ( iso Pr), SiMe3, SiHMe2, SiH2Me, SiH3, SiHClMe, SiHCl2, SiMe2CH2CH3, SiMe2CH=CH2, and SiHMeCH=CH2.

[0041] NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso Pr).

[0042] R 1 and R 4 The hydrocarbon groups in each of the above are independently a methyl group (Me), an ethyl group (Et), an n-propyl group (Pr), an isopropyl group ( iso Pr), n-butyl group (Bu), sec-butyl group ( sec Bu), isobutyl group ( iso Bu), tert-butyl group ( tert Bu), and isomers thereof.

[0043] In the present invention, R 4 and R 5 may be different from each other, and preferably, R 4 and R 5 are different from each other.

[0044] The alkoxide in the present invention is a compound in which the hydrogen (H) of the hydroxyl group (OH) of an alcohol is substituted with a metal, i.e., a silicon alkoxide in which silicon (Si) is substituted as the metal.

[0045] The silicon precursor compounds of the present invention can be prepared by the methods shown in Reaction Scheme 1 and Reaction Scheme 2 below.

[0046] [ka]

[0047] In the method for preparing a silicon precursor according to Reaction Scheme 1, an alkoxide compound is reacted with a secondary amine to prepare a silicon precursor compound represented by Formula 1. This is carried out by a first step of reacting a chlorosilane compound represented by Formula 2 with an alcohol compound represented by Formula 3 to form an alkoxide compound, and a second step of reacting the alkoxide compound with a secondary amine represented by Formula 5 to prepare the silicon precursor compound represented by Formula 1.

[0048] As a specific example of Reaction Scheme 1, n is 1 and R 2 When is hydrogen (H), silicon compounds of formula 8 can be prepared as shown in Reaction Scheme 2 below.

[0049] [ka]

[0050] In Reaction Schemes 1 and 2, n is 1 or 2 and R 1is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 R 2 and R 3 are hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 R 4 is a linear or branched, saturated or unsaturated hydrocarbon group (e.g., having 1 to 6 carbon atoms) or an isomer thereof, and R 5 is methyl (Me), ethyl (Et), isopropyl ( iso Pr), SiMe3, SiHMe2, SiH2Me, SiH3, SiHClMe, SiHCl2, SiMe2CH2CH3, SiMe2CH=CH2, and SiHMeCH=CH2.

[0051] In the method for preparing silicon precursors according to Reaction Schemes 1 and 2, in the first step, a chlorosilane compound is reacted with an alcohol compound in a non-polar solvent at a low temperature of about -40°C to carry out a substitution reaction between Cl and the alcohol compound, followed by filtration and distillation under reduced pressure to form an alkoxide compound.

[0052] In the second step, the alkoxide compound formed in the first step is reacted with a secondary amine represented by formula 5, and the resulting salt and unreacted materials are removed by filtration and vacuum distillation to obtain a silicon precursor compound.

[0053] The silicon precursor compounds of the present invention may be prepared by alternative methods as shown in Reaction Scheme 3 or Reaction Scheme 4 below.

[0054] [ka]

[0055] [ka]

[0056] In the method for preparing silicon precursors according to Reaction Schemes 3 and 4, an alkoxide compound is reacted with an alkylaminosilane to prepare the silicon precursor compound.

[0057] As shown in Reaction Scheme 4, this can be achieved by reacting a chlorosilane compound of formula 11 with a primary amine of formula 12 to form an alkylaminosilane of formula 13 in a first step, reacting the alkylaminosilane with an alkyl-lithium (alkyl-Li) to form a lithium-containing alkylaminosilane of formula 14 in a second step, and reacting the compound of formula 14 with an alkoxide compound of formula 10 to prepare a silicon precursor compound of formula 15 in a third step.

[0058] The alkoxide compounds represented by formula 10 can be formed by reacting a chlorosilane compound represented by formula 9 with an alcohol compound represented by formula 3, as shown in Reaction Scheme 3.

[0059] Another method for preparing a silicon precursor compound is carried out similarly to Reaction Scheme 4, except that the alkoxide compound used in Reaction Scheme 4 is a compound of Formula 17, prepared according to Reaction Scheme 5 below to prepare a silicon precursor compound of Formula 18, as shown in Reaction Scheme 6.

[0060] [ka]

[0061] [ka]

[0062] In Reaction Schemes 3 to 6, R 1 is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 R 2 , R 2 ', R 3 , and R 3 ' represents hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 R 0 is a linear or branched, saturated or unsaturated hydrocarbon group (e.g., having 1 to 6 carbon atoms) or an isomer thereof, and R 9 , R 10 , and R 11 are each one selected from hydrogen (H), chlorine (Cl), a methyl group (Me), an ethyl group (CH2CH3), and a vinyl group (CH=CH2).

[0063] In the method for preparing silicon precursors according to Reaction Schemes 4 and 6, in the first step, triorganochlorosilane as a chlorosilane compound is reacted with a primary amine in a non-polar solvent at a low temperature of about -40°C to carry out a substitution reaction of Cl with the amine, followed by filtration and distillation under reduced pressure to form an alkylaminosilane of Formula 13.

[0064] In the second step, the alkylaminosilane formed in the first step is reacted with alkyl-lithium (alkyl-Li) in a non-polar solvent at a low temperature of about −40° C. to carry out a Li displacement reaction to form a compound of formula 14.

[0065] Here, alkyl-Li is lithium containing an alkyl group having 1 to 10 carbon atoms, examples of which include methyllithium, ethyllithium, propyllithium, butyllithium, and isobutyllithium.

[0066] In the third step, after reaction with the silane compound represented by formula 10 or 17, the reaction product salt (LiCl) and unreacted materials are removed by filtration, and distillation is carried out under reduced pressure to obtain the silicon precursor compound.

[0067] The non-polar solvent used in Reaction Schemes 1 to 6 may be, but is not limited to, hexane, n-pentane, etc. Any non-polar solvent commonly used by those skilled in the art may be used.

[0068] The silicon precursor compound of the present invention can be selected from the group consisting of the following compounds (1) to (56).

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] Furthermore, according to the method for preparing a silicon-containing thin film of the present invention, a silicon-containing thin film can be formed by chemical vapor deposition (CVD), plasma-enhanced chemical vapor deposition (PECVD), or atomic layer deposition (ALD), which are well known to those skilled in the art, using a silicon precursor compound represented by Formula 1. The silicon-containing thin film according to the present invention can be any one selected from the group consisting of a silicon oxide (SiO2) film, a silicon oxycarbide (SiOC) film, a silicon nitride (SiN) film, a silicon oxynitride (SiON) film, a silicon carbonitride (SiCN) film, a silicon oxycarbonitride (SiOCN) film, and a silicon carbide (SiC) film, but is not limited thereto. The silicon-containing thin film according to the present invention is preferably a silicon oxide (SiO2) film.

[0074] The silicon oxide film of the present invention is preferably deposited by atomic layer deposition. Atomic layer deposition includes providing a substrate in a reactor, supplying a silicon precursor compound to the reactor, purging the reactor with a purge gas, supplying an oxygen source to the reactor to react with the silicon precursor compound to form the silicon oxide film, and purging the reactor with the purge gas. The purge gas is preferably selected from the group consisting of, but not limited to, nitrogen, helium, argon, and mixtures thereof. The oxygen source is preferably selected from the group consisting of, but not limited to, oxygen, peroxide, oxygen plasma, water vapor, water vapor plasma, hydrogen peroxide, an ozone source, and mixtures thereof. The oxygen source is preferably ozone (O).

[0075] The step of forming the silicon oxide film may be carried out at a temperature of about 200°C to about 600°C, and is preferably carried out at a temperature of about 400°C.

[0076] Aspects of the invention

[0077] The present invention will be described in detail below with reference to examples. [Example]

[0078] In Example 1, compound (1), diisopropyldimethoxysilanamine, was prepared as the silicon precursor compound.

[0079] In the first step, dichlorodiisopropylsilanamine (1,1-dichloro-N,N-diisopropylsilanamine) was prepared. 200 g (1.48 mol) of trichlorosilane (HSiCl) and 1,279 g (17.72 mol) of n-pentane were placed in a 5-liter flask under an anhydrous and inert atmosphere. While maintaining the temperature at -40°C, 306 g (3.03 mol) of diisopropylamine (((CH)CH)NH) was slowly added and stirred for 3 hours. After stirring, the diisopropylamine hydrochloride (((CH)CH)NHCl) was removed by filtration and purified under reduced pressure to yield 264.5 g (1.48 mol) of dichlorodiisopropylsilanamine (((CH)CH)NSiHCl) (89% yield).

[0080] 1 H-NMR(C6D6):δ 0.92(d,12H(N(CH(CH3)2)2)),3.09(m,2H(N(CH(CH3)2)2)2)),5.65(s,1H(-SiH))

[0081] In the second step, 161 g (1.11 mol) of dichlorodiisopropylsilanamine (((CH3)2CH)2NSiHCl2) prepared in the first step and 1,430 g (19.82 mol) of n-pentane were placed in a 5-L flask under an anhydrous and inert atmosphere. While maintaining the temperature at -40°C, 274 g (2.71 mol) of triethylamine (N(CH2CH3)3) was slowly added, followed by the slow addition of 109 mL (2.71 mol) of methanol (CH3OH). The temperature was then gradually raised to room temperature, followed by stirring for 3 hours. After stirring was completed, the triethylamine salt (N(CH2CH3)3HCl) was removed by filtration, and the solvent was then removed under reduced pressure to obtain 156.8 g (1.32 mol) of the silicon precursor compound diisopropyldimethoxysilanamine (((CH3)2CH)2NSiH(OCH3)2) (yield: 62.3%).

[0082] FIG. 1 shows the hydrogen nuclear magnetic resonance (NMR) spectra of the silicon precursor compound prepared according to Example 1 of the present invention.1 1H-NMR spectrum is shown, as shown, the silicon precursor compound prepared in Example 1 was confirmed to be diisopropyldimethoxysilanamine.

[0083] 1 H-NMR(C6D6):δ 1.11(d,12H(N(CH(CH3)2)2)),3.18(m,2H(N(CH(CH3)2)2))),3.40(s,6H(OCH3)2),4.63(s,1H(-SiH)) [Example]

[0084] In Example 2, compound (2), ethoxymethylsilylisopropyltrimethylsilanamine, was prepared as the silicon precursor compound.

[0085] First, chloro(ethoxy)(methyl)silane was prepared as the silane compound required to prepare the silicon precursor compound. 250 g (2.17 mol) of dichloromethylsilane (CH3SiHCl2) and 1,568 g (21.73 mol) of n-pentane were placed in a 1-liter flask under an anhydrous and inert atmosphere. While maintaining the temperature at -40°C, 230 g (2.28 mol) of triethylamine (N(CH2CH3)3) was slowly added, followed by the slow addition of ethanol (CH3CH2OH) over a period of 1 hour. The temperature of the reaction solution was then gradually raised to room temperature, followed by stirring for 3 hours. After stirring was complete, triethylamine hydrochloride (N(CH2CH3)3HCl) was removed by filtration, and the mixture was purified under reduced pressure to yield 185 g (1.49 mol) of chloroethoxymethylsilane (CH3CH2OSiHMeCl) (yield: 69%).

[0086] 1 H-NMR(C6D6):δ 0.22(d,3H(-SiCH3)),1.01(t,3H(-OCH2CH3)),3.59(m,2H(-OCH2CH3)),5.14(m,1H(-SiH))

[0087] In the first step of Example 2, isopropylaminotrimethylsilazane was prepared. 220 g (2.03 mol) of chlorotrimethylsilane ((CH3)3SiCl) and 2,190 g (30 mol) of n-pentane were placed in a 1-liter flask under an anhydrous and inert atmosphere. While maintaining the temperature at -40°C, 251 g (4.25 mol) of isopropylamine ((CH3)2CHNH2) was slowly added, followed by stirring for 3 hours. After stirring was completed, the isopropylamine hydrochloride ((CH3)2CHNH3Cl) was removed by filtration, followed by vacuum distillation to remove the solvent, yielding 205 g (1.5 mol) of isopropylaminotrimethylsilazane ((CH3)2CHNSiH(CH3)3) (77% yield).

[0088] 1 H-NMR(C6D6):δ 0.06(s,9H(SiCH3)3),0.96(d,6H(NCH(CH3)2)),2.92(m,1H(NCH(CH3)2))

[0089] In the second step of Example 2, 200 g (1.38 mol) of isopropylaminotrimethylsilazane ((CH)CHNSiH(CH)) prepared in the first step and 1,186 g (13.76 mol) of hexane were placed in a 1-liter flask under an anhydrous and inert atmosphere. While maintaining the temperature at -40°C, 402 mL (1.45 mol) of 2.5 M n-butyllithium (n-BuLi) was slowly added. The temperature was then gradually raised to room temperature, followed by stirring for 12 hours.

[0090] Next, in the third step of Example 2, 171.5 g (1.38 mol) of chloroethoxymethylsilane (CH3CH2OSiHMeCl) was gradually added to the mixed solution from the second step while maintaining the temperature at -20°C, followed by stirring for 6 hours or more. After stirring was completed, the lithium chloride (LiCl) salt was removed by filtration. The solvent in the filtrate was removed under reduced pressure, followed by distillation to obtain 181 g (1.38 mol) of ethoxymethylsilylisopropyltrimethylsilanamine (CH3CH2OSiHMeNiPrSiMe3) as a silicon precursor compound (yield: 60%).

[0091] FIG. 2 shows the hydrogen nuclear magnetic resonance (NMR) spectra of the silicon precursor compound prepared according to Example 2 of the present invention. 1 1H-NMR spectrum is shown, as shown, the silicon precursor compound prepared in Example 2 was confirmed to be ethoxymethylsilylisopropyltrimethylsilanamine.

[0092] 1 H-NMR(C6D6):δ 0.18(s,9H(-Si(CH3)3)),0.28(d,3H(-SiHCH3)),1.15(t,3H(-O(CH2CH3))),1.17(m,6H(- SiNCH(CH3)2)),3.20(m,1H(-NCH(CH3)2)),3.65(m,2H(-O(CH2CH3)))),4.95(m,1H(-SiH)) [Example]

[0093] In Example 3, compound (3), dimethylsilylethoxyisopropylmethylsilanamine, was prepared as the silicon precursor compound.

[0094] In the first step of Example 3, isopropyldimethylsilanamine was prepared. A 1-liter flask under an anhydrous and inert atmosphere was charged with 100 g (1.06 mol) of chlorodimethylsilane ((CH)SiHCl) and 1,143 g (15.0 mol) of n-pentane. While maintaining the temperature at -40°C, 128 g (2.17 mol) of isopropylamine ((CH)CHNH) was slowly added, followed by stirring for 3 hours. After stirring was completed, the isopropylamine hydrochloride ((CH)CHNHCl) was removed by filtration and then purified under reduced pressure to yield 101 g (1.06 mol) of isopropyldimethylsilanamine ((CH)CHNHSiH(CH)). Yield: 82%.

[0095] 1 H-NMR(C6D6):δ 0.08(s,6H(Si(CH3)2)),0.96(d,6H(NCH(CH3)2)),2.95(m,1H(NCH(CH3)2))),4.71(m,1H(-SiH))

[0096] In the second step of Example 3, 100 g (0.85 mol) of isopropyldimethylsilanamine ((CH)CHNHSiH(CH)) prepared in the first step and 367 g (5.0 mol) of hexane were placed in a 1-liter flask under an anhydrous and inert atmosphere. 257 mL (0.90 mol) of 2.5 M n-butyllithium (n-BuLi) was slowly added while maintaining the temperature at -40°C. The temperature was then gradually raised to room temperature, followed by stirring for 12 hours.

[0097] Next, in the third step of Example 3, 177 g (0.85 mol) of chloroethoxymethylsilane (CH3CH2OSiHMeCl) was slowly added to the mixed solution from the second step while maintaining the temperature at -20°C, followed by stirring for 6 hours or more. After stirring was completed, the lithium chloride (LiCl) salt was removed by filtration. The solvent in the filtrate was removed under reduced pressure, followed by distillation to obtain 122 g of dimethylsilylethoxyisopropylmethylsilanamine (CH3CH2OSiHMeNiPrSiHMe2) as a silicon precursor compound (yield: 70%).

[0098] FIG. 3 shows the hydrogen nuclear magnetic resonance (NMR) spectra of the silicon precursor compound prepared according to Example 3 of the present invention. 1 1H-NMR spectrum is shown, as shown, the silicon precursor compound prepared in Example 3 was confirmed to be dimethylsilylethoxyisopropylmethylsilanamine.

[0099] 1 H-NMR(C6D6):δ 0.20(m,6H(-SiH(CH3)2)),1.14(t,3H(-O(CH2CH3)),1.17(m,6H(-SiNCH2(CH3)2)),3.27(m,1H (NCH(CH3)2)),3.65(m,2H(-O(CH2CH3))),4.75(m,1H(-SiH(CH3)2)),4.88(m,1H(-SiH(CH3)2)) [Example]

[0100] In Example 4, compound (25), diethylaminooxymethylsilylisopropyltrimethylsilanamine, was prepared as the silicon precursor compound.

[0101] In the first step of Example 4, isopropylaminotrimethylsilazane was prepared in the same manner as in Example 2.

[0102] In the second step of Example 4, chloro(methyl)silyl)diethylhydroxylamine was prepared. A 1-liter flask under an anhydrous and inert atmosphere was charged with 100 g (0.86 mol) of dichloromethylsilane (CHSiHCl) and 1,140 g (13.04 mol) of n-pentane. While maintaining the temperature at -40°C, 92.4 g (0.92 mol) of triethylamine ((CHCHN)) was added, followed by the slow addition of 81.4 g (0.92 mol) of diethylhydroxylamine ((CHCHNOH)) over a 1-hour period. The temperature was then raised to room temperature, followed by stirring for 3 hours. After stirring was completed, triethylamine hydrochloride ((CH3CH2)3NHCl) was removed by filtration, and the solvent was subsequently removed by distillation under reduced pressure to obtain 132 g (0.78 mol) of chloro(methyl)silyl)diethylhydroxylamine ((CH3CH2)2NOSiHMeCl) (yield: 90%).

[0103] 1 H-NMR(C6D6):δ 0.34(d,3H(SiCH3)),0.83(m,6H-ON(CH2CH3)2),2.66(m,4H(-ON(CH2CH3)2),5.23(m,1H(-SiH))

[0104] In the third step of Example 4, 14 g (0.12 mol) of isopropylaminotrimethylsilazane ((CH3)2CHNHSi(CH3)3) prepared in the first step and 74.2 g (0.86 mol) of hexane were placed in a 1-liter flask under an anhydrous and inert atmosphere. While maintaining the temperature at -40°C, 52 mL (0.13 mol) of 2.5 M n-butyllithium (n-BuLi) was slowly added. The temperature was then gradually raised to room temperature, followed by stirring for 2 hours. Next, while maintaining the mixture at -20°C, 30 g (0.12 mol) of chloro(methyl)silyl)diethylhydroxylamine ((CH3CH2)2NOHSiCH3Cl) prepared in the second step was slowly added, followed by stirring for 6 hours at room temperature. After stirring was completed, the lithium chloride (LiCl) salt was removed by filtration. The solvent in the filtrate was removed under reduced pressure, followed by purification to obtain 20 g of the silicon precursor compound, diethylaminooxymethylsilylisopropyltrimethylsilanamine ((CH3CH2)2NOCH3HSiNCH(CH3)2Si(CH3)3) (yield: 62%).

[0105] 1 H-NMR(C6D6):δ 0.12(s,9H(-Si(CH3)3),0.25(d,3H(-SiHCH3)),1.07(m,6H(-ON(CH2CH3)2),1.20(m,6H(- NCH(CH3)2)),2.76(m,4H(-ON(CH2CH3)2)),3.29(m,1H(-NCH(CH3)2))),4.69(m,1H(-SiH))

[0106] FIG. 4 shows the hydrogen nuclear magnetic resonance (NMR) spectra of the silicon precursor compound prepared according to Example 4 of the present invention. 1 1H-NMR spectrum is shown, as shown, the silicon precursor compound prepared in Example 4 was confirmed to be diethylaminooxymethylsilylisopropyltrimethylsilanamine. [Example]

[0107] In Example 5, compound (35), isopropylmethoxytetramethyltrimethylsilyldisilanamine, was prepared as a silicon precursor compound.

[0108] In the first step of Example 5, chloromethoxytetramethyldisilane was prepared. A 1-liter flask under an anhydrous and inert atmosphere was charged with 193 g (1.03 mol) of dichlorotetramethyldisilane (Cl(CH)SiSi(CH)Cl) and 2,754 g (38.15 mol) of n-pentane. While maintaining the temperature at -40°C, 99 g (0.98 mol) of triethylamine (N(CHCH)) was slowly added, followed by 31 g (0.98 mol) of methanol (HOCH). The temperature was then gradually raised to room temperature, followed by stirring for 16 hours. After stirring, the triethylamine salt (N(CHCH)HCl) was removed by filtration, followed by removal of the solvent under reduced pressure, yielding 119 g (0.65 mol) of chloromethoxytetramethyldisilane (CHO(CH)SiSi(CH)Cl) (67% yield).

[0109] 1 H-NMR(CDCl3):δ 0.32(s,6H(-Si(OCH3)(CH3)2)),0.53(s,6H(-SiCl(CH3)2)),3.48(s,3H(-OCH3))

[0110] In the second step of Example 5, 129 g (0.89 mol) of isopropyltrimethylsilanamine ((CH)CHNHSi(CH)) and 535 g (6.20 mol) of n-hexane were placed in a 1-L flask under an anhydrous and inert atmosphere. 372 mL (0.93 mol) of 2.5 M n-butyllithium (n-BuLi) was slowly added while maintaining the temperature at -15°C. The temperature was then gradually raised to room temperature, followed by stirring for 2 hours.

[0111] Next, in the third step of Example 5, while the mixed solution from the second step was maintained at -3°C, 162 g (0.89 mol) of chloromethoxytetramethyldisilane (CHO(CH)SiSi(CH)Cl) prepared in the first step was slowly added to it. The temperature was then raised to room temperature and stirred for 16 hours. After stirring was completed, the lithium chloride (LiCl) salt was removed by filtration. The solvent in the filtrate was removed under reduced pressure, followed by distillation to obtain 138 g (0.48 mol) of isopropylmethoxytetramethyltrimethylsilyldisilanamine (CHO(CH)SiSi(CH)N(CH(CH))Si(CH)) as a silicon precursor compound (yield: 54%).

[0112] FIG. 5 shows the hydrogen nuclear magnetic resonance (NMR) spectra of the silicon precursor compound prepared according to Example 5 of the present invention. 1 1H-NMR spectrum is shown, as shown, the silicon precursor compound prepared in Example 5 was confirmed to be isopropylmethoxytetramethyltrimethylsilyldisilanamine.

[0113] 1 H-NMR(C6D6):δ 0.21(s,9H(-Si(CH3)3)),0.26(s,6H(-Si(CH3)2N-)),0.34(s,6H(CH3OSi(CH3)2 Si-)),1.18(d,6H(-NCH(CH3)2)),3.29(s,3H(CH3O-)),3.37(m,1H(-NCH(CH3)2)) [Example]

[0114] In Example 6, compound (36), dimethylsilylisopropylmethoxytetramethyldisilanamine, was prepared as a silicon precursor compound.

[0115] In the first step of Example 6, chloromethoxytetramethyldisilane was prepared in the same manner as in Example 5.

[0116] In the second step of Example 6, 92 g (0.78 mol) of isopropyldimethylsilanamine ((CH)CHNHSiH(CH)) prepared in the first step of Example 3 and 472 g (5.48 mol) of n-hexane were placed in a 1-liter flask under an anhydrous and inert atmosphere. 328 mL (0.82 mol) of 2.5 M n-butyllithium (n-BuLi) was slowly added while maintaining the temperature at -15°C. The temperature was then gradually raised to room temperature, followed by stirring for 2 hours.

[0117] Next, in the third step of Example 6, while maintaining the mixed solution from the second step at -3°C, 162 g (0.89 mol) of chloromethoxytetramethyldisilane (CHO(CH)SiSi(CHCl)) was slowly added thereto, and the temperature was then raised to room temperature and stirred for 16 hours. After stirring was completed, the lithium chloride (LiCl) salt was removed by filtration. The solvent in the filtrate was removed under reduced pressure, followed by distillation to obtain 108 g (0.41 mol) of dimethylsilylisopropylmethoxytetramethyldisilanamine (CHO(CH)SiSi(CH)N(CH(CH))SiH(CH)) as a silicon precursor compound (yield: 52%).

[0118] FIG. 6 shows the hydrogen nuclear magnetic resonance (NMR) spectra of the silicon precursor compound prepared according to Example 6 of the present invention. 1 1H-NMR spectrum is shown, as shown, the silicon precursor compound prepared in Example 6 was confirmed to be dimethylsilylisopropylmethoxytetramethyldisilanamine.

[0119] 1 H-NMR(C6D6):δ 0.22(d,6H(-SiH(CH3)2)),0.27(s,6H(-Si(CH3)2N-)),0.32(s,6H(CH3OSi(CH3)2Si-)),1.16( d,6H(-NCH(CH3)2)),3.28(m,1H(-NCH(CH3)2)),3.30(s,3H(CH3O-)),4.76(m,1H(-SiH(CH3)2))

[0120] Thermogravimetric analysis (TGA) was performed to analyze the thermal properties of the silicon precursor compounds prepared in Examples 1 to 6. The results are shown in FIG.

[0121] 7, the silicon precursor compounds of Examples 4, 5, and 6 exhibit volatility over various temperature ranges, including temperatures below 220°C, between 220°C and 500°C, and above 500°C. In particular, the silicon precursor compounds of Examples 1, 2, and 3 exhibit volatility over temperature ranges below 170°C, between 170°C and 500°C, and above 500°C, which are lower than the temperature ranges of the silicon precursor compounds of Examples 4, 5, and 6. Therefore, they are excellent silicon precursors capable of forming silicon-containing thin films over a wide temperature range.

[0122] The above results indicate that all silicon precursor compounds prepared according to the examples of the present invention exhibit sufficient volatility to be applied in atomic layer deposition (ALD) or chemical vapor deposition (CVD).

[0123] To confirm that the silicon precursor compounds prepared in Examples 2, 3, 5, and 6 have vapor pressures suitable for preparing silicon oxide thin films by deposition, their vapor pressures were measured, and the results are shown in Figure 8.

[0124] As shown in Figure 8, all of the silicon precursor compounds of Examples 2, 3, 5, and 6 exhibited high vapor pressures of 10 Torr or more at about 100°C. Among them, Example 3 exhibited a higher vapor pressure at a lower temperature than the other examples.

[0125] The above vapor pressure results show that all of the silicon precursor compounds prepared according to the examples of the present invention exhibit high vapor pressures of 10 Torr or more at low temperatures of about 100°C or less, which are sufficient for application in atomic layer deposition (ALD) or chemical vapor deposition (CVD).

[0126] Preparation of silicon-containing thin films

[0127] Here, the preparation of a silicon oxide thin film SiO2 will be described as a representative example, but is not limited to this. Silicon-containing thin films known in the art, such as SiN, SiO2, and SiCN, can also be formed.

[0128] An experiment was conducted to form a silicon oxide thin film on a silicon substrate by atomic layer deposition (ALD) using the silicon compound ethoxymethylsilylisopropyltrimethylsilanamine of Example 2 as a precursor. An ALD reactor was used, which uses a double showerhead to supply the precursor and reactive gas (O3) separately in the vertical direction.

[0129] Table 1 and FIG. 9 show specific conditions for depositing a silicon oxide thin film.

[0130] [Table 1]

[0131] The thin film deposited as described above was analyzed for the composition of the silicon oxide thin film by AES (Auger Electron Spectroscopy) using X-ray photoelectron spectroscopy, and the results are shown in FIG.

[0132] As shown in FIG. 10, the thin films deposited using the silicon precursor compounds prepared according to the present invention were high purity silicon oxide thin films.

[0133] Furthermore, as shown in FIGS. 11 to 13, the step coverage and thickness of the silicon oxide thin film were observed using a transmission electron microscope (TEM).

[0134] Table 2 below shows the results of analyzing the properties of certain silicon oxide thin films.

[0135] [Table 2]

[0136] As shown in Table 2, a thick film with a thickness of 300 Å was formed at a high deposition rate at a substrate temperature of 400°C and a deposition rate of 0.27 Å / cycle. The O / Si composition ratio of the formed thin film suggested that a high-purity silicon-containing thin film was formed.

[0137] As mentioned above, the silicon precursor compounds prepared according to the present invention are suitable for forming high-purity silicon-containing thin films at high deposition rates by atomic layer deposition (ALD).

[0138] The above-described embodiments are merely intended to illustrate preferred embodiments of the present invention. The scope of the present invention is not limited to the described embodiments. Those skilled in the art will recognize that various changes, modifications, and substitutions may be made within the technical spirit of the present invention and the scope of the claims. It is understood that such embodiments fall within the scope of the present invention.

Claims

1. A silicon precursor compound, The following formula (1): 【Chemical 1】 (Wherein, n is 1 or 2, R 1 represents a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 One of the following is selected from R 2 and R 3 are respectively hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 One of the following is selected from R 4 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, R 5 is methyl (Me), ethyl (Et), isopropyl ( iso Pr), SiMe 3 , SiHMe 2 , SiH 2 Me, SiH 3 , SiHClMe, SiHCl 2 , SiMe 2 CH 2 CH 3 , SiMe 2 CH=CH 2 , and SiHMeCH═CH 2 and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso Pr) is any one selected from the group consisting of:

2. The following compounds (1) to (56): 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 2. The silicon precursor compound of claim 1 selected from the group consisting of:

3. 1. A method for preparing a silicon precursor compound, comprising: The alkoxide compound is reacted with a secondary amine, or the alkoxide compound is reacted with an alkylaminosilane to form a compound of the following formula 1: 【Chemistry 6】 (Wherein, n is 1 or 2, R 1 represents a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 One of the following is selected from R 2 and R 3 are respectively hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 One of the following is selected from R 4 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, R 5 is methyl (Me), ethyl (Et), isopropyl ( iso Pr), SiMe 3 , SiHMe 2 , SiH 2 Me, SiH 3 , SiHClMe, SiHCl 2 , SiMe 2 CH 2 CH 3 , SiMe 2 CH=CH 2 , and SiHMeCH═CH 2 and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso 3. A method for preparing a silicon precursor compound, comprising preparing a silicon precursor compound represented by the formula (I) wherein R is an integer of 1 to 3, and R is an integer of 1 to 3.

4. The alkoxide compound is represented by the following formula 4: 【Chemistry 7】 (Wherein, n is 1 or 2, R 1 represents a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 One of the following is selected from R 2 and R 3 are respectively hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 One of the following is selected from NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso 4. The method for preparing the silicon precursor compound according to claim 3, wherein the silicon precursor compound is a compound represented by the formula (I) or (II), wherein the compound is any one selected from the group consisting of:

5. The reaction of the alkoxide compound with the secondary amine affords a compound of the following formula 8: 【Chemistry 8】 (In the formula, R 1 represents a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 One of the following is selected from R 3 is hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 One of the following is selected from R 4 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, R 5 is methyl (Me), ethyl (Et), isopropyl ( iso Pr), SiMe 3 , SiHMe 2 , SiH 2 Me, SiH 3 , SiHClMe, SiHCl 2 , SiMe 2 CH 2 CH 3 , SiMe 2 CH=CH 2 , and SiHMeCH═CH 2 and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso 4. The method for preparing a silicon precursor compound according to claim 3, wherein a silicon precursor compound represented by the formula (I) is prepared, wherein the silicon precursor compound is any one selected from the group consisting of:

6. The reaction of the alkoxide compound with the alkylaminosilane yields a compound of the following formula 15 or 18: 【Chemistry 9】 【Chemistry 10】 (In the formula, R 1 represents a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 One of the following is selected from R 2 , R 2 ', R 3 , and R 3 ' respectively represent hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 One of the following is selected from R 0 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, R 9 , R 10 , and R 11 represent hydrogen (H), chlorine (Cl), a methyl group (Me), and an ethyl group (CH 2 CH 3 ), and vinyl groups (CH═CH 2 ) and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso 4. The method for preparing a silicon precursor compound according to claim 3, wherein a silicon precursor compound represented by the formula (I) is prepared, wherein the silicon precursor compound is any one selected from the group consisting of:

7. The silicon precursor compound is the following compounds (1) to (56): 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 4. A method for preparing the silicon precursor compound of claim 3, wherein the silicon precursor compound is selected from the group consisting of:

8. 1. A method for preparing a silicon-containing thin film, comprising: The silicon-containing thin film has the following formula 1: 【Chemistry 15】 (Wherein, n is 1 or 2, R 1 represents a linear or branched saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms, its isomers, and NR 7 R 8 One of the following is selected from R 2 and R 3 are respectively hydrogen (H), chlorine (Cl), methyl (Me), methoxy (MeO), ethoxy (EtO), n-propoxy, and isopropoxy ( iso PrO), n-butoxy, isobutoxy ( iso BuO), sec-butoxy ( sec BuO), tert-butoxy ( tert BuO), and NR 7 R 8 One of the following is selected from R 4 is a linear or branched, saturated or unsaturated hydrocarbon group or an isomer thereof, R 5 is methyl (Me), ethyl (Et), isopropyl ( iso Pr), SiMe 3 , SiHMe 2 , SiH 2 Me, SiH 3 , SiHClMe, SiHCl 2 , SiMe 2 CH 2 CH 3 , SiMe 2 CH=CH 2 , and SiHMeCH═CH 2 and NR 7 R 8 R in 7 and R 8 are methyl (Me), ethyl (Et), and isopropyl ( iso 2. A method for preparing a silicon-containing thin film, comprising the steps of:

9. The silicon precursor compound is the following compounds (1) to (56): 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 9. The method for preparing a silicon-containing thin film of claim 8, wherein the silicon-containing thin film is selected from the group consisting of:

10. 10. The method for preparing a silicon-containing thin film of claim 8, wherein the silicon-containing thin film is deposited by chemical vapor deposition, plasma-enhanced chemical vapor deposition, or atomic layer deposition.

11. The silicon-containing thin film is silicon oxide (SiO 2 9. The method for preparing a silicon-containing thin film according to claim 8, wherein the silicon-containing thin film is any one selected from the group consisting of a silicon oxycarbide (SiOC) film, a silicon nitride (SiN) film, a silicon oxynitride (SiON) film, a silicon carbonitride (SiCN) film, a silicon oxycarbonitride (SiOCN) film, and a silicon carbide (SiC) film.

12. The silicon-containing thin film is silicon oxide (SiO 2 ) film, wherein the silicon oxide film is deposited by atomic layer deposition, and the atomic layer deposition comprises: providing a substrate to a reactor; providing the silicon precursor compound to the reactor; purging the reactor with a purge gas; providing an oxygen source to the reactor to react with the silicon precursor compound to form a silicon oxide film; and purging the reactor with a purge gas.

13. the purge gas is selected from the group consisting of nitrogen, helium, argon, and mixtures thereof; 13. The method for preparing a silicon-containing thin film of claim 12, wherein the oxygen source is selected from the group consisting of oxygen, peroxide, oxygen plasma, water vapor, water vapor plasma, hydrogen peroxide, an ozone source, and mixtures thereof.

14. The oxygen source is ozone (O 3 13. The method for preparing a silicon-containing thin film of claim 12, wherein

15. 13. The method for preparing a silicon-containing thin film of claim 12, wherein the step of forming the silicon oxide film is carried out at a temperature of about 200°C to about 600°C.

Citation Information

Patent Citations

  • KR2011-0017404